# EDGAR Filing Document

**Accession Number:** 0001585608
**File Stem:** 0001193125-25-201351
**Filing Date:** 2025-9
**Character Count:** 145260
**Document Hash:** 325b6cdeeb7246bbee8b903bbb94a255
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001193125-25-201351.hdr.sgml**: 20250911

**ACCESSION NUMBER**: 0001193125-25-201351

**CONFORMED SUBMISSION TYPE**: 8-K

**PUBLIC DOCUMENT COUNT**: 14

**CONFORMED PERIOD OF REPORT**: 20250909

**ITEM INFORMATION**: Entry into a Material Definitive Agreement

**ITEM INFORMATION**: Unregistered Sales of Equity Securities

**ITEM INFORMATION**: Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year

**ITEM INFORMATION**: Financial Statements and Exhibits

**FILED AS OF DATE**: 20250911

**DATE AS OF CHANGE**: 20250911

**FILER**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** Jaguar Health, Inc.
- **CENTRAL INDEX KEY:** 0001585608
- **STANDARD INDUSTRIAL CLASSIFICATION:** PHARMACEUTICAL PREPARATIONS [2834]
- **ORGANIZATION NAME:** 03 Life Sciences
- **EIN:** 000000000
- **STATE OF INCORPORATION:** DE
- **FISCAL YEAR END:** 1231

**FILING VALUES:**
- **FORM TYPE:** 8-K
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 001-36714
- **FILM NUMBER:** 251308893

**BUSINESS ADDRESS:**
- **STREET 1:** 200 PINE STREET SUITE 400
- **CITY:** SAN FRANCISCO
- **STATE:** CA
- **ZIP:** 94104
- **BUSINESS PHONE:** 415-371-8300

**MAIL ADDRESS:**
- **STREET 1:** 200 PINE STREET SUITE 400
- **CITY:** SAN FRANCISCO
- **STATE:** CA
- **ZIP:** 94104

**FORMER COMPANY:**
- **FORMER CONFORMED NAME:** Jaguar Animal Health, Inc.
- **DATE OF NAME CHANGE:** 20130830

?xml version='1.0' encoding='ASCII'? 8-K

### UNITED STATES

### SECURITIES AND EXCHANGE COMMISSION

#### WASHINGTON, D.C. 20549

### FORM 8-K

#### CURRENT REPORT

#### Pursuant to Section 13 or 15(d)

#### of the Securities Exchange Act of 1934

#### Date of Report (Date of earliest event reported): September 9, 2025

## Jaguar Health, Inc.

#### (Exact name of Registrant as Specified in Its Charter)

---

| | | |
|:---|:---|:---|
| **Delaware** | **001-36714** | **46-2956775** |
| **(State or Other Jurisdiction**<br> **of Incorporation)** | **(Commission**<br> **File Number)** | **(IRS Employer**<br> **Identification No.)** |

---

---

| | |
|:---|:---|
| **200 Pine Street** |  |
| **Suite 400** |  |
| **San Francisco, California** | **94104** |
| **(Address of Principal Executive Offices)** | **(Zip Code)** |

---

#### Registrant's Telephone Number, Including Area Code: (415) 371-8300

#### (Former Name or Former Address, if Changed Since Last Report)
Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:

☐ Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

☐ Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

☐ Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

☐ Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

#### Securities registered pursuant to Section 12(b) of the Act:

---

| | | |
|:---|:---|:---|
| **Title of each class** | **Trading<br>Symbol(s)** | **Name of each exchange**<br> **on which registered** |
| Common Stock, Par Value $0.0001 Per Share | JAGX | The Nasdaq Stock Market |

---

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§ 230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§ 240.12b-2 of this chapter).

Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

------

---

| | |
|:---|:---|
| **Item 1.01** | **Entry into a Material Definitive Agreement.**  |

---

#### PIPE Financing
On or around September 9, 2025, Jaguar Health, Inc. (the "Company") entered into securities purchase agreements (each a "PIPE Purchase Agreement" and collectively, the "PIPE Purchase Agreements") with certain investors named therein (collectively, the "Purchasers"), pursuant to which the Company agreed to issue and sell to the Purchasers in a private placement an aggregate of approximately 951 shares (the "Preferred Shares") of Series N Perpetual Preferred Stock, par value $0.0001 per share, of the Company ("Series N Preferred Stock"), for an aggregate purchase price of approximately $2.38 million (the "Private Placement"). The Private Placement closed on September 10, 2025, subject to customary closing conditions as set forth in the PIPE Purchase Agreements. The Company intends to use the proceeds from the Private Placement for working capital and general corporate purposes, and repayment of certain existing notes.

Subject to the terms of the Series N Preferred Stock set forth in Item 3.02 below, following the Stockholder Approval (as defined hereunder), each share of Series N Preferred Stock is exchangeable for shares of Common Stock. The terms of the Series N Preferred Stock are set forth in a Certificate of Designation of Preferences, Rights and Limitations of Series N Perpetual Preferred Stock (the "Certificate of Designation") filed with the Secretary of State of Delaware and effective on September 9, 2025. A description of the terms of the Series N Preferred Stock is included under Item 5.03 of this Current Report and is incorporated herein by reference.

Under the PIPE Purchase Agreements, the Company is required to use commercially reasonable efforts to hold a meeting of stockholders at the earliest practical date, but in no event later than 90 days after the closing of the Private Placement, for the purpose of obtaining the Stockholder Approval. If the Company does not obtain the Stockholder Approval at the first meeting, upon the written request of holders of the Preferred Shares representing at least a majority of the amount of the outstanding Preferred Shares, the Company shall use commercially reasonable efforts to call another meeting of stockholders within four months of the first meeting of stockholders.

The PIPE Purchase Agreements include representations, warranties, and covenants customary for a transaction of this type. In addition, the Company agreed to file a registration statement on Form S-3 with the U.S. Securities and Exchange Commission (the "SEC") within 30 days following the closing of the Private Placement, to register the resale of (i) shares of the Common Stock issued or issuable by the Company upon exchange of the Preferred Shares (the "Exchange Shares" and, together with the Preferred Shares, collectively the "PIPE Shares"), and (ii) any securities issued or issuable upon any stock split, dividend or other distribution, recapitalization or similar event, or any price adjustment as a result of such stock splits, reverse stock splits or similar events with respect to the securities referenced in (i). The PIPE Shares were offered and sold in reliance upon exemptions from registration pursuant to Section 4(a)(2) under the Securities Act of 1933, as amended ("Securities Act"), and Rule 506 of Regulation D promulgated thereunder.

The foregoing summary of the PIPE Purchase Agreements does not purport to be complete and is subject to, and qualified in its entirety by the form of PIPE Purchase Agreement attached as Exhibit 10.1 to this Current Report on Form 8-K and is incorporated herein by reference.

Neither the disclosures on this Form 8-K nor the attached press releases shall constitute an offer to sell or the solicitation of an offer to buy the securities described herein or therein, nor shall there be any sale of such securities in any state or jurisdiction in which such an offer, solicitation or sale would be unlawful prior to registration or qualification under the securities laws of any such state or jurisdiction.

---

| | |
|:---|:---|
| **Item 3.02** | **Unregistered Sales of Equity Securities.**  |

---

The information contained above in Item 1.01 is hereby incorporated by reference into this Item 3.02 in its entirety. The shares of Series N Preferred Stock were offered and sold in reliance upon exemptions from registration pursuant to 4(a)(2) under the Securities Act, and Rule 506 of Regulation D promulgated thereunder. The offering was made to "accredited investors" (as defined by Rule 501 under the Securities Act).

------

---

| | |
|:---|:---|
| **Item 5.03** | **Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year.**  |

---

#### Series N Certificate of Designation
As disclosed under Items 1.01 and 3.02 above, in connection with the Private Placement, the Company agreed to issue shares of Series N Preferred Stock to the Purchasers. The preferences, rights, limitations and other matters relating to the Series N Preferred Stock are set forth in the Certificate of Designation, which the Company filed with the Secretary of State of the State of Delaware on September 9, 2025. The Certificate of Designation became effective with the Secretary of State of the State of Delaware upon filing.

The Certificate of Designation authorizes the Company to issue up to 2,000 of its 4,475,074 authorized shares of preferred stock as Series N Preferred Stock.

*Dividends* 

Holders of shares of Series N Preferred Stock (the "Holders") will not be entitled to receive any dividends on shares of Series N Preferred Stock.

*Voting Rights* 

The Series N Preferred Stock shall vote together with shares of Common Stock on an as-converted basis from time to time, and not as a separate class, at any annual or special meeting of stockholders of the Company, and may act by written consent in the same manner as holders of shares of the Common Stock, in either case upon the following basis: each share of the Series N Preferred Stock shall be entitled to such number of votes equal to the quotient obtained by dividing (i) the $2,500 stated value of each share of Series N Preferred Stock (the "Stated Value") by (ii) the Minimum Price (which is defined as the lower of: (i) the Nasdaq official closing price (as reflected on Nasdaq.com) immediately preceding a given date or (ii) the average Nasdaq official closing price of the Common Stock (as reflected on Nasdaq.com) for the five (5) trading days immediately preceding such given date) of the Common Stock on the date of the PIPE Purchase Agreements. In addition, as long as any shares of Series N Preferred Stock are outstanding, the Company shall not, without the affirmative vote of the Holders of a majority of the then outstanding shares of the Series N Preferred Stock, (a) alter or change adversely the powers, preferences or rights given to the Series N Preferred Stock or alter or amend the Certificate of Designation or (b) enter into any agreement with respect to any of the foregoing.

Notwithstanding the foregoing, in no event shall a Holder (together with such Holder's Affiliates and Attribution Parties (both terms as defined in the Certificate of Designation)) be entitled to vote, on an as-converted basis and in aggregate with respect to any shares of Common Stock and preferred stock of the Company beneficially owned by such Holder or any Affiliates or Attribution Parties of such Holder, more than 19.99% of the Company's outstanding shares of Common Stock as of the applicable record date (the "Voting Cap"). The Voting Cap shall be appropriately adjusted for any stock splits, reverse stock splits, stock dividends, reclassifications, reorganization, recapitalizations or other similar transaction.

*Liquidation Rights* 

In the event of any voluntary or involuntary liquidation, dissolution or winding up of the Company or Deemed Liquidation Event (as defined below), each share of Series N Preferred Stock shall be entitled to be paid, out of the assets of the Company available for distribution to its stockholders, before any distribution or payment out of the assets of the Company may be made to or set aside for the holders of any Junior Stock (as defined in the Certificate of Designation) and subject to the rights of the holders of any class or series of securities ranking senior to or on parity with Series N Preferred Stock upon any such Liquidation Event and the rights of the Company's depositors and other creditors, an amount per share of Series N Preferred Stock equal to the Stated Value at such time (as applicable, the "Liquidation Amount"). If upon any such liquidation, dissolution or winding up of the Company (other than a Chapter 7 bankruptcy) or Deemed Liquidation Event, the assets of the Company available for distribution to its stockholders shall be insufficient to pay the Liquidation Amount, the Holders of shares of Series N

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Preferred Stock and the holders of all Parity Stock (as defined in the Certificate of Designation) shall share ratably in any distribution of the assets available for distribution in proportion to the respective amounts which would otherwise be payable in respect of the shares held by them upon such distribution if all amounts payable on or with respect to such shares were paid in full. Following the payment of the Liquidation Amount, if there are any remaining assets of the Company available for distribution to its stockholders, the Series N Preferred Stock shall not participate in such distributions. Notwithstanding the foregoing, if in the event of a dissolution or winding up of the Company in connection with a Chapter 7 bankruptcy, the assets of the Company available for distribution to its stockholders shall be insufficient to pay the Liquidation Amount, the Holders with respect to their shares of Series N Preferred Stock shall be entitled to receive out of such assets the same amount that each share of the Common Stock would receive as if each outstanding share of Series N Preferred Stock were, immediately prior to the applicable record date, fully converted (disregarding solely for such purposes any conversion or exchange limitations hereunder) to shares of Common Stock by dividing (i) Liquidation Amount by (ii) the Exchange Price (which, for each share of Series N Preferred Stock shall be, unless otherwise provided in the Certificate of Designation, equal to $1.20, subject to adjustments), which amounts shall be paid pari passu with all holders of Common Stock.

Each of the following events shall be considered a "Deemed Liquidation Event": (a) (A) a merger or consolidation in which the Company is a constituent party and in which the stockholders of the Company immediately prior to such merger or consolidation do not continue to hold a majority of the voting power of the Company or any successor entity following such merger or consolidation; or (b) the sale, lease, transfer, exclusive license or other disposition, in a single transaction or series of related transactions, by the Company or any subsidiary of the Company of all or substantially all the assets of the Company and its subsidiaries taken as a whole, or the sale or disposition (whether by merger, consolidation or otherwise) of one or more subsidiaries of the Company if substantially all of the assets of the Company and its subsidiaries taken as a whole are held by such subsidiary or subsidiaries, except where such sale, lease, transfer, exclusive license or other disposition is to a wholly owned subsidiary of the Company. The Company shall not have the power to effect a Deemed Liquidation Event unless the agreement or plan of merger or consolidation for such transaction (the "Merger Agreement') provides that the consideration payable to the Series N Preferred Stock shall be allocated in accordance with the Certificate of Designation.

*Conversion Rights* 

Series N Preferred Stock shall not be convertible into Common Stock or any other security of the Company and does not otherwise have any conversion rights.

*Company Mandatory Exchange Rights* 

The Company has the right to exchange, at any time after the Stockholder Approval is obtained and from time to time and at its sole discretion, part or all of the then outstanding shares of Series N Preferred Stock held by any holder thereof for shares of Common Stock (the "Mandatory Exchange Shares") at an exchange ratio equal to the Stated Value divided by the Exchange Price. Notwithstanding the foregoing, the Company will not have the right to consummate a Mandatory Exchange if: (a) the Stockholder Approval is not obtained, (b) the issuance of such Exchange Shares would cause such holder, together with its Affiliates, to beneficially own in excess of 19.99% of the number of shares of Common Stock outstanding on the date of issuance (including for such purpose the shares of Common Stock issuable upon such issuance) immediately after giving effect to the issuance of the Mandatory Exchange Shares; (c) any of the Mandatory Exchange Conditions (as defined below) has not been satisfied as of the applicable Exchange Date. The Exchange Cap shall be appropriately adjusted for any reorganization, recapitalization, non-cash dividend, stock split, reverse stock split or other similar transaction. Following delivery of an Exchange Notice (as defined in the Certificate of Designation), the Company may not deliver another Exchange Notice to a Holder for at least three (3) Trading Days.

"Exchange Conditions" mean: (a) with respect to the applicable Exchange Date, all of the Exchange Shares would be (i) registered for trading under applicable federal and state securities laws, (ii) freely tradable under Rule 144, or (iii) otherwise freely tradable without the need for registration under any applicable federal or state securities laws; (b) the applicable Mandatory Exchange Shares would be eligible for immediate resale by the holder; (c) no Event of Default (as defined below) shall have occurred under the Certificate of Designation; and (e) the closing price of the Common Stock on the Trading Day immediately prior to the applicable Exchange Date is equal to or greater than the Exchange Price.

------

*Mutual Exchange Right* 

At any time and from time to time after the date that Stockholder Approval is obtained, the Company and any Holder may mutually agree to exchange part or all of the then outstanding shares of Series N Preferred Stock held by such Holder for shares of Common Stock (the "Mutual Exchange Shares") pursuant to Section 3(a)(9) of the Securities Act at a price per share equal to the Minimum Price of the Common Stock as of the date of the agreement for such exchange.

*Covenants* 

Until such time as no shares of Series N Stock remain outstanding, the Company, and as applicable, its Subsidiaries, will at all times comply with the following covenants: (a) the Company will timely file on the applicable deadline all reports required to be filed with the Securities and Exchange Commission (the "Commission") pursuant to Sections 13 or 15(d) of the Securities Exchange Act of 1934, as amended (the "Exchange Act"), and will take all reasonable action under its control to ensure that adequate current public information with respect to the Company, as required in accordance with Rule 144 of the Securities Act, is publicly available, and will not terminate its status as an issuer required to file reports under the Exchange Act even if the Exchange Act or the rules and regulations thereunder would permit such termination; (b) the Company will cause the Common Stock to be listed or quoted for trading on any of NYSE, NYSE American, Nasdaq, CBOE, OTCQB or OTCQX until a Fundamental Transaction (as defined below); (c) the Company shall ensure that, until a Fundamental Transaction, trading in the Common Stock will not be suspended, halted, chilled, frozen, reach zero bid or otherwise cease trading on the Company's principal trading market for a period of more than five (5) consecutive Trading Days; (d) the Company shall not enter into any agreement or otherwise agree to any covenant, condition, or obligation that locks up, restricts in any way or otherwise prohibits the Company from issuing Equity Securities to any Holder or any Affiliate of such Holder.

The covenants set forth in sub-section (d) will also apply to all Subsidiaries.

"Fundamental Transaction" means: (i) the Company, directly or indirectly, in one or more related transactions effects any merger or consolidation of the Company with or into another Person (as defined in the Certificate of Designation) other than any subsidiary or any Affiliate of the Company, whereby the stockholders of the Company immediately prior to such merger or consolidation do not own, directly or indirectly, at least 50% of the voting power of the surviving entity immediately after such merger or consolidation, (ii) the Company, directly or indirectly, effects any sale, lease, license, assignment, transfer, conveyance or other disposition of all or substantially all of its assets in one or a series of related transactions, (iii) any, direct or indirect, purchase offer, tender offer or exchange offer (whether by the Company or another Person) is completed pursuant to which holders of Common Stock are permitted to sell, tender or exchange their shares for other securities, cash or property and has been accepted by the holders of 50% or more of the outstanding Common Stock, (iv) the Company, directly or indirectly, in one or more related transactions effects any reclassification, reorganization or recapitalization of the Common Stock or any compulsory share exchange pursuant to which the Common Stock is effectively converted into or exchanged for other securities, cash or property, (v) the Company, directly or indirectly, in one or more related transactions consummates a stock or share purchase agreement or other business combination (including, without limitation, a reorganization, recapitalization, spin-off, merger or scheme of arrangement) with another Person or group of Persons whereby such other Person or group acquires more than 50% of the outstanding shares of Common Stock (not including any shares of Common Stock held by the other Person or other Persons making or party to, or associated or affiliated with the other Persons making or party to, such stock or share purchase agreement or other business combination), (vi) the sale or spin-off of any Subsidiaries, and (vii) a Deemed Liquidation Event. For the avoidance of doubt, any license agreement entered into in the ordinary course of business by the Company or any Subsidiary will not be considered a Fundamental Transaction.

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*Covenant Default* 

The Required Holders may elect to declare an "Event of Default" if any of the following conditions or events shall occur and be continuing: (a) the Company or any Subsidiary fails to fully comply with any covenant, obligation or agreement of the Company or any Subsidiary in the Certificate of Designation, and such failure, if known to the Required Holders and reasonably possible of cure, is not cured within thirty (30) calendar days following notice to cure from the Required Holders; (b) the Company fails to pay any amount due and payable to the Holders pursuant to and as required by the Certificate of Designation, and such failure, if known to the Holders and reasonably possible of cure, is not cured within five (5) Trading Days following notice of notice to cure from the Required Holders; (c) the Company shall (1) apply for or consent to the appointment of, or the taking of possession by, a receiver, custodian, trustee or liquidator; (2) make a general assignment for the benefit of the Company's creditors; or (3) commence a voluntary case under the U.S. Bankruptcy Code as now and hereafter in effect, or any successor statute; or (d) a proceeding or case shall be commenced, without the application or consent of the Company, in any court of competent jurisdiction, seeking (1) liquidation, reorganization or other relief with respect to it or its assets or the composition or readjustment of its debts, or (2) the appointment of a trustee, receiver, custodian, liquidator or the like of any substantial part of its assets, and, in each case, such proceedings or case shall remain uncontested for 30 days or shall continue undismissed, or an order, judgment or decree approving or ordering any of the foregoing shall be entered and continue unstayed and in effect, for a period of 60 days, if in the United States, or 90 days, if outside of the United States; or an order for relief against the Company shall be entered in an involuntary case under any bankruptcy, insolvency, composition, readjustment of debt, liquidation of assets or similar Law of any jurisdiction.

If an Event of Default has occurred (i) the Required Holders may, by notice to the Company (the "Notice of the Forced Redemption"), force the Company to redeem all of the issued and outstanding shares of Series N Preferred Stock then held by the Holders for a price equal to (1) the Stated Value of all such shares of Series N Preferred Stock, with such Stated Value to be paid in such number of shares of Common Stock equal to the quotient obtained by dividing the Stated Value by the Exchange Price; plus (2) any and all other amounts (the "Other Amounts") due and payable to the Holders pursuant to the Certificate of Designation, with such Other Amounts to be paid in such number of shares of Common Stock equal to the quotient obtained by dividing the Other Amounts by the Exchange Price (with the shares of Common Stock issuable pursuant to aforementioned sub-sections (1) and (2), collectively, the "Forced Redemption Shares"); (ii) the Holders shall have the right to pursue any other remedies that the Required Holders may have under applicable law and/or in equity; and (iii) the Holders shall have the right to seek and receive injunctive relief from a court prohibiting the Company from issuing any of its Common Stock or Preferred Stock to any party unless the all shares of Series N Preferred Stock owned by the Holders are redeemed in full simultaneously with such issuance. Notwithstanding the foregoing, Holder will not have the right to force the Corporation to redeem any shares of Series N Preferred Stock and issue any Forced Redemption Shares if: (a) the Stockholder Approval is not obtained; or (b) the issuance of such Forced Redemption Shares would cause such Holder, together with its Affiliates, to beneficially own in excess of the Maximum Percentage immediately after giving effect to the issuance of the Forced Redemption Shares. For the avoidance of doubt, any Forced Redemption Shares that would cause the Holder to exceed the Maximum Percentage shall be held in abeyance and shall not be issued until such time, if ever, as the Holder's right to receive such shares would not result in a violation of the Maximum Percentage.

In the event that any Holder incurs expenses in the enforcement of its rights, including but not limited to reasonable attorneys' fees, then the Company shall immediately reimburse such Holder the reasonable costs thereof.

*Trading Market* 

There is no established trading market for any of the Series N Preferred Stock, and we do not expect a market to develop. We do not intend to apply for a listing for any of the Series N Preferred Stock on any securities exchange or other nationally recognized trading system. Without an active trading market, the liquidity of the Series N Preferred Stock will be limited.

*Maximum Percentage* 

In no event may shares of Common Stock be issued to any Holder that would cause such Holder's beneficial ownership to exceed the Maximum Percentage, which is 19.99% of the number of shares of Common Stock outstanding on a given date (including for such purpose the shares of Common Stock issuable upon such issuance).

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The foregoing description of the Certificate of Designation does not purport to be complete and is qualified in its entirety by reference to the full text of the Certificate of Designation, a copy of which is filed as Exhibit 3.1 to this Current Report and is incorporated by reference herein.

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| | |
|:---|:---|
| **Item 9.01** | **Financial Statements and Exhibits.**  |

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*(d) Exhibits* 

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| | |
|:---|:---|
| **Exhibit**<br>**No.** | **Description** |
| 3.1 | [Certificate of Designation of Preferences, Rights and Limitations of Series N Perpetual Preferred Stock.](d947025dex31.htm) |
| 10.1 | [Form of Securities Purchase Agreements.](d947025dex101.htm) |
| 104 | Cover Page Interactive Data File (embedded within the inline XBRL document) |

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#### SIGNATURES
Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

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| | | |
|:---|:---|:---|
|  |  | JAGUAR HEALTH, INC. |
| Date: September 11, 2025 | By: | /s/ Lisa A. Conte |
|  |  | Lisa A. Conte |
|  |  | Chief Executive Officer & President |

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## Exhibit 3.1

**Exhibit 3.1** 

JAGUAR HEALTH, INC.

CERTIFICATE OF DESIGNATION OF PREFERENCES,

RIGHTS AND LIMITATIONS

OF

SERIES N PERPETUAL PREFERRED STOCK

Pursuant to Section 151 of the

General Corporation Law of the State of Delaware

The undersigned, Lisa A. Conte and Carol R. Lizak, do hereby certify that:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;1. They are the Chief Executive Officer/President and Chief Financial Officer, respectively, of Jaguar Health, Inc., a Delaware corporation (the "<u>Corporation</u>").

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2. The following resolutions were duly adopted by the board of directors of the Corporation (the "<u>Board of Directors</u>"):

WHEREAS, the certificate of incorporation of the Corporation provides for a class of its authorized stock known as preferred stock, consisting of 4,475,074 shares, $0.0001 par value per share, issuable from time to time in one or more series;

WHEREAS, the Board of Directors is authorized to fix the dividend rights, dividend rate, voting rights, conversion rights, rights and terms of redemption and liquidation preferences of any wholly unissued series of preferred stock and the number of shares constituting any series and the designation thereof, of any of them; and

WHEREAS, it is the desire of the Board of Directors, pursuant to its authority as aforesaid, to fix the rights, preferences, restrictions and other matters relating to a series of the preferred stock, which shall consist of 2,000 shares of the preferred stock which the Corporation has the authority to issue, as follows:

NOW, THEREFORE, BE IT RESOLVED, that the Board of Directors does hereby provide for the issuance of a series of preferred stock for cash or exchange of other securities, rights, powers, property, or other lawful consideration and does hereby fix and determine the rights, preferences, restrictions and other matters relating to such series of preferred stock as follows:

**TERMS OF SERIES N PERPETUAL PREFERRED STOCK** 

<u>Section</u> <u>1.</u> <u>Definitions</u>. For the purposes hereof, the following terms shall have the following meanings:

"<u>Affiliate</u>" means any Person that, directly or indirectly through one or more intermediaries, controls or is controlled by or is under common control with a Person, as such terms are used in and construed under Rule 405 of the Securities Act.

"<u>Certificate</u>" means this Certificate of Designation.

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"<u>Commission</u>" means the United States Securities and Exchange Commission.

"<u>Common Stock</u>" means the Corporation's voting common stock, par value $0.0001 per share, and stock of any other class of securities into which such securities may hereafter be reclassified or changed.

"<u>Common Stock Equivalents</u>" means any securities of the Corporation or its subsidiaries which would entitle the holder thereof to acquire at any time Common Stock, including, without limitation, any debt, Preferred Stock, rights, options, warrants or other instrument that is at any time convertible into or exercisable or exchangeable for, or otherwise entitles the holder thereof to receive, Common Stock.

"<u>Deemed Liquidation Event</u>" shall have the meaning set forth in <u>Section</u> <u>5(b)</u>.

"<u>Definitive Agreement Date</u>" means the date of the definitive agreement with respect to the first of such aggregated transactions for the sale and issuance of the shares of Series N Preferred Stock.

"<u>Delaware Courts</u>" shall have the meaning set forth in Section 12(b).

"<u>Equity</u> <u>Securities</u>" means Common Stock, Common Stock Equivalents, Preferred Stock and any option, warrant, or right to subscribe for, acquire or purchase Common Stock or Preferred Stock.

"<u>Exchange Cap</u>" means the maximum number of Exchange Shares and Forced Redemption Shares, in aggregate, that could be issued to Holders without violating The Nasdaq Capital Market rules related to the aggregation of offerings under Nasdaq Listing Rule 5635(d), if applicable. The Exchange Cap shall be appropriately adjusted for any reorganization, recapitalization, non-cash dividend, stock split, reverse stock split or other similar transaction.

"<u>Mandatory Exchange Conditions</u>" mean: (a) with respect to the applicable Exchange Date, all of the Exchange Shares would be (i) registered for trading under applicable federal and state securities laws, (ii) freely tradable under Rule 144, or (iii) otherwise freely tradable without the need for registration under any applicable federal or state securities laws; (b) the applicable Mandatory Exchange Shares would be eligible for immediate resale by Holder; (c) no Event of Default shall have occurred hereunder; (d) the Common Stock is trading on Nasdaq, NYSE, OTCQB or OTCQX as of the applicable Exchange Date; and (e) the closing price of the Common Stock on the Trading Day immediately prior to the applicable Exchange Date is equal to or greater than the Exchange Price.

"<u>Exchange Date</u>" means the date that an Exchange Notice is delivered by the Corporation to a Holder.

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"<u>Exchange Notice</u>" means a notice delivered by the Corporation to a Holder specifying the number of shares of Series N Preferred Stock to be exchanged and the number of Mandatory Exchange Shares to be issued.

"<u>Exchange Price</u>" for each share of Series N Preferred Stock shall be, unless otherwise provided in this Certificate, equal to $1.20, subject to adjustment for reverse and forward stock splits, stock dividends, stock combinations and other similar transactions of the Common Stock that occur after the Original Issue Date.

"<u>Exchange Ratio</u>" for each share of Series N Preferred Stock shall be equal to the Stated Value divided by the applicable Exchange Price.

"<u>Exchange Shares</u>" means, collectively, the Mandatory Exchange Shares and the Mutual Exchange Shares issued and issuable upon exchange of the shares of Series N Preferred Stock.

"<u>Fundamental Transaction</u>" means: (i) the Corporation, directly or indirectly, in one or more related transactions effects any merger or consolidation of the Corporation with or into another Person other than any subsidiary or any Affiliate of the Corporation, whereby the stockholders of the Corporation immediately prior to such merger or consolidation do not own, directly or indirectly, at least 50% of the voting power of the surviving entity immediately after such merger or consolidation, (ii) the Corporation, directly or indirectly, effects any sale, lease, license, assignment, transfer, conveyance or other disposition of all or substantially all of its assets in one or a series of related transactions, (iii) any, direct or indirect, purchase offer, tender offer or exchange offer (whether by the Corporation or another Person) is completed pursuant to which holders of Common Stock are permitted to sell, tender or exchange their shares for other securities, cash or property and has been accepted by the holders of 50% or more of the outstanding Common Stock, (iv) the Corporation, directly or indirectly, in one or more related transactions effects any reclassification, reorganization or recapitalization of the Common Stock or any compulsory share exchange pursuant to which the Common Stock is effectively converted into or exchanged for other securities, cash or property, (v) the Corporation, directly or indirectly, in one or more related transactions consummates a stock or share purchase agreement or other business combination (including, without limitation, a reorganization, recapitalization, spin-off, merger or scheme of arrangement) with another Person or group of Persons whereby such other Person or group acquires more than 50% of the outstanding shares of Common Stock (not including any shares of Common Stock held by the other Person or other Persons making or party to, or associated or affiliated with the other Persons making or party to, such stock or share purchase agreement or other business combination), (vi) the sale or spin-off of any Subsidiaries, and (vii) a Deemed Liquidation Event (as defined below). For the avoidance of doubt, any license agreement entered into in the ordinary course of business by the Corporation or any Subsidiary will not be considered a Fundamental Transaction.

"<u>Holder</u>" shall have the meaning given such term in <u>Section</u> <u>2</u>.

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"<u>Junior Stock</u>" means the Common Stock and any other class or series of stock of the Corporation now existing or hereafter authorized over which Series N Preferred Stock has preference or priority in the distribution of assets on any voluntary or involuntary liquidation, dissolution or winding up of the Corporation.

"<u>Liquidation Event</u>" shall have the meaning set forth in <u>Section</u> <u>5</u>.

"<u>Maximum Percentage</u>" means 19.99% of the number of shares of Common Stock outstanding on such date (including for such purpose the shares of Common Stock issuable upon such issuance). For purposes of calculating the Maximum Percentage, beneficial ownership of Common Stock will be determined pursuant to Section 13(d) of the 1934 Act.

"<u>Minimum Price</u>" means, with respect to a given date, the lower of: (i) the Nasdaq official closing price (as reflected on Nasdaq.com) immediately preceding such date or (ii) the average Nasdaq official closing price of the Common Stock (as reflected on Nasdaq.com) for the five (5) Trading Days immediately preceding such date.

"<u>Original Issue Date</u>" means the date of the first issuance of any shares of the Series N Preferred Stock regardless of the number of transfers of any particular shares of Series N Preferred Stock.

"<u>Parity Stock</u>" means the Series L Perpetual Preferred Stock, par value of $0.0001 per share, of the Corporation, the Series M Perpetual Preferred Stock, par value of $0.0001 per share, of the Corporation, and any class or series of stock of the Corporation hereafter authorized that ranks equally with the Series N Preferred Stock in the distribution of assets on any liquidation, dissolution or winding up of the Corporation.

"<u>Person</u>" means an individual or corporation, partnership, trust, incorporated or unincorporated association, joint venture, limited liability company, joint stock company, government (or an agency or subdivision thereof) or other entity of any kind.

"<u>Preferred Stock</u>" means any class or series of preferred stock issued by the Corporation.

"<u>Required Holders</u>" means the Holders of at least a majority of the outstanding Series N Preferred Stock.

"<u>Securities Act</u>" means the Securities Act of 1933, as amended, and the rules and regulations promulgated thereunder.

"<u>Senior Stock</u>" means any class or series of stock of the Corporation hereafter authorized which has preference or priority over the Series N Preferred Stock in the distribution of assets on any voluntary or involuntary liquidation, dissolution or winding up of the Corporation.

"<u>Series N Preferred Stock</u>" shall have the meaning set forth in <u>Section</u> <u>2</u>.

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"<u>Stated Value</u>" means $2,500.00.

"<u>Stockholder Approval</u>" means such approval as required by the applicable Nasdaq Stock Market Rules by the stockholders of the Corporation with respect to the exchange and/or redemption of shares of Series N Preferred Stock and the issuance of the shares of Common Stock issuable upon exchange and/or redemption of the Series N Preferred Stock.

"<u>Subsidiaries</u>" means any wholly- or partially-owned subsidiaries of the Corporation that exist now or may be created in the future.

"<u>Trading Day</u>" means a day on which the principal Trading Market is open for business.

"<u>Trading Market</u>" means any of the following markets or exchanges on which the Common Stock is listed or quoted for trading on the date in question: the NYSE American, the Nasdaq Capital Market, the Nasdaq Global Market, the Nasdaq Global Select Market, or the New York Stock Exchange (or any successors to any of the foregoing).

"<u>Transfer Agent</u>" means Equiniti Trust Company, LLC, the current transfer agent of the Corporation with a mailing address of 55 Challenger Road, Floor 2, Ridgefield Park, NJ 07660 and an electronic mailing address of helpast@equiniti.com, and any successor transfer agent of the Corporation.

<u>Section</u> <u>2.</u> <u>Designation, Amount and Par Value</u>. This series of preferred stock shall be designated as Series N Perpetual Preferred Stock (the "<u>Series N Preferred Stock</u>") and the number of shares so designated shall be Two Thousand (2,000) (each holder of the Series N Preferred Stock a "<u>Holder</u>" and collectively, the "<u>Holders</u>"). Each share of Series N Preferred Stock shall have a par value of $0.0001 per share. The Series N Preferred Stock will initially be issued in book-entry form.

<u>Section</u> <u>3.</u> <u>Dividends</u>. Holders will not be entitled to receive any dividends on shares of Series N Preferred Stock.

<u>Section</u> <u>4.</u> <u>Voting Rights</u>. Except as otherwise provided herein or as otherwise required by law, the Series N Preferred Stock shall vote together with shares of Common Stock on an as-converted basis from time to time, and not as a separate class, at any annual or special meeting of stockholders of the Corporation, and may act by written consent in the same manner as holders of shares of the Common Stock, in either case upon the following basis: each share of the Series N Preferred Stock shall be entitled to such number of votes equal to the quotient obtained by dividing (i) the Stated Value by (ii) the Minimum Price of the Common Stock on the Definitive Agreement Date. In addition, as long as any shares of Series N Preferred Stock are outstanding, the Corporation shall not, without the affirmative vote of the Holders of a majority of the then outstanding shares of the Series N Preferred Stock, (a) alter or change adversely the powers, preferences or rights given to the Series N Preferred Stock or alter or amend this Certificate or (b) enter into any agreement with respect to any of the foregoing.

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Notwithstanding the foregoing in this <u>Section</u> <u>4</u>, in no event shall a Holder (together with such Holder's Affiliates, and any Persons acting as a group together with such Holder or any of such Holder's Affiliates (such Persons, "<u>Attribution Parties</u>")) be entitled to vote, on an as-converted basis and in aggregate with respect to any shares of Common Stock and preferred stock of the Corporation beneficially owned by such Holder or any Affiliates or Attribution Parties of such Holder, more than 19.99% of the Corporation's outstanding shares of Common Stock as of the applicable record date (the "<u>Voting Cap</u>"). The Voting Cap shall be appropriately adjusted for any stock splits, reverse stock splits, stock dividends, reclassifications, reorganization, recapitalizations or other similar transaction.

<u>Section</u> <u>5.</u> <u>Liquidation Rights</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a) <u>Preferential Payments to Holders of Series N Preferred Stock</u>. In the event of any voluntary or involuntary liquidation, dissolution or winding up of the Corporation or Deemed Liquidation Event (as defined below) (each, a "<u>Liquidation Event</u>"), each share of Series N Preferred Stock shall be entitled to be paid, out of the assets of the Corporation available for distribution to its stockholders, before any distribution or payment out of the assets of the Corporation may be made to or set aside for the holders of any Junior Stock and subject to the rights of the holders of any class or series of securities ranking senior to or on parity with Series N Preferred Stock upon any such Liquidation Event and the rights of the Corporation's depositors and other creditors, an amount per share of Series N Preferred Stock equal to the Stated Value at such time (as applicable, the "<u>Liquidation Amount</u>"). If upon any such liquidation, dissolution or winding up of the Corporation (other than a Chapter 7 bankruptcy) or Deemed Liquidation Event, the assets of the Corporation available for distribution to its stockholders shall be insufficient to pay the Liquidation Amount, the Holders of shares of Series N Preferred Stock and the holders of all Parity Stock shall share ratably in any distribution of the assets available for distribution in proportion to the respective amounts which would otherwise be payable in respect of the shares held by them upon such distribution if all amounts payable on or with respect to such shares were paid in full. Following the payment of the Liquidation Amount, if there are any remaining assets of the Corporation available for distribution to its stockholders, the Series N Preferred Stock shall not participate in such distributions. Notwithstanding the foregoing, if in the event of a dissolution or winding up of the Corporation in connection with a Chapter 7 bankruptcy, the assets of the Corporation available for distribution to its stockholders shall be insufficient to pay the Liquidation Amount, the Holders with respect to their shares of Series N Preferred Stock shall be entitled to receive out of such assets the same amount that each share of the Common Stock would receive as if each outstanding share of Series N Preferred Stock were, immediately prior to the applicable record date, fully converted (disregarding solely for such purposes any conversion or exchange limitations hereunder) to shares of Common Stock by dividing (i) Liquidation Amount by (ii) the Exchange Price, which amounts shall be paid pari passu with all holders of Common Stock.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b) <u>Deemed Liquidation Events</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(i) <u>Definition.</u> Each of the following events shall be considered a " <u>Deemed Liquidation Event</u> ":

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(A) a merger or consolidation in which the Corporation is a constituent party and in which the stockholders of the
Corporation immediately prior to such merger or consolidation do not continue to hold a majority of the voting power of the Corporation or any successor entity following such merger or consolidation; or

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(B) the sale, lease, transfer, exclusive license or other disposition, in a single transaction or series of related
transactions, by the Corporation or any subsidiary of the Corporation of all or substantially all the assets of the Corporation and its subsidiaries taken as a whole, or the sale or disposition (whether by merger, consolidation or otherwise) of one
or more subsidiaries of the Corporation if substantially all of the assets of the Corporation and its subsidiaries taken as a whole are held by such subsidiary or subsidiaries, except where such sale, lease, transfer, exclusive license or other
disposition is to a wholly owned subsidiary of the Corporation.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c) <u>Effecting a Deemed Liquidation Event</u>. The Corporation shall not have the power to effect a Deemed Liquidation Event unless the agreement or plan of merger or consolidation for such transaction (the "<u>Merger Agreement'</u>) provides that the consideration payable to the Series N Preferred Stock shall be allocated in accordance with Section 5(a).

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d) <u>Amount Deemed Paid or Distributed.</u> The amount deemed paid or distributed to the Holders upon any such merger, consolidation, sale, transfer, exclusive license, or other disposition shall be the cash or the value of the property, rights or securities paid or distributed to such Holders by the Corporation or the acquiring person, firm or other entity. The value of such property, right or securities shall be determined in good faith by the Board.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(e) <u>Allocation of Escrow and Contingent Consideration</u>. In the event of a Deemed Liquidation Event<u>,</u> if any portion of the consideration payable to the Holders is payable only upon satisfaction of contingencies (the "<u>Additional Consideration</u>"), the merger agreement or other agreement related to such event shall provide that (a) the portion of such consideration that is not Additional Consideration (such portion, the ''<u>Initial Consideration</u>") shall be allocated among the Holders in accordance with Section 5(a) as if the Initial Consideration were the only consideration payable in connection with such Deemed Liquidation Event; and (b) any Additional Consideration which becomes payable to the Holders upon satisfaction of such contingencies shall be allocated among the Holders in accordance with Section 5(a) after taking into account the previous payment of the Initial Consideration as part of the same transaction.

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<u>Section</u> <u>6.</u> <u>Conversion Rights</u>. Series N Preferred Stock shall not be convertible into Common Stock or any other security of the Corporation, and does not otherwise have any conversion rights.

<u>Section</u> <u>7.</u> <u>Reserved</u>.

<u>Section</u> <u>8.</u> <u>Exchange Rights</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a) <u>Company Mandatory Exchange Right</u>. The Corporation has the right to exchange, at any time after the Stockholder Approval is obtained and from time to time, at the Corporation's sole discretion, part or all of the then outstanding shares of Series N Preferred Stock held by any Holder for shares of Common Stock (the "<u>Mandatory Exchange Shares</u>") at the Exchange Ratio (the "<u>Mandatory Exchange</u>"). Notwithstanding the foregoing, the Corporation will not have the right to consummate a Mandatory Exchange if: (a) the Stockholder Approval is not obtained, (b) the issuance of such Mandatory Exchange Shares would cause such Holder, together with its Affiliates, to beneficially own in excess of the Maximum Percentage immediately after giving effect to the issuance of the Mandatory Exchange Shares; or (c) any of the Mandatory Exchange Conditions has not been satisfied as of the applicable Exchange Date. Following delivery of an Exchange Notice, the Corporation may not deliver another Exchange Notice to a Holder for at least three (3) Trading Days.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b) <u>Mutual Exchange Right</u>. At any time and from time to time after the date that Stockholder Approval is obtained, the Company and any Holder may mutually agree to exchange part or all of the then outstanding shares of Series N Preferred Stock held by such Holder for shares of Common Stock (the "<u>Mutual Exchange Shares</u>") pursuant to Section 3(a)(9) of the Securities Act at a price per share equal to the Minimum Price of the Common Stock as of the date of the agreement for such exchange.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c) <u>Fractional Shares</u>. The Corporation shall have the authority to issue fractional shares of Series N Preferred Stock.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d) <u>Transfer Taxes and Expenses</u>. The issuance of Exchange Shares on exchange of this Series N Preferred Stock shall be made without charge to any Holder for any documentary stamp or similar taxes that may be payable in respect of the issue or delivery of such Exchange Shares, provided that the Corporation shall not be required to pay any tax that may be payable in respect of any transfer involved in the issuance and delivery of any such Exchange Shares upon exchange in a name other than that of the Holders of such shares of Series N Preferred Stock and the Corporation shall not be required to issue or deliver such Exchange Shares unless or until the Person or Persons requesting the issuance thereof shall have paid to the Corporation the amount of such tax or shall have established to the satisfaction of the Corporation that such tax has been paid. The Corporation shall pay all Transfer Agent fees required for same-day processing of any Notice of Exchange and all fees to the Depository Trust Company (or another established clearing corporation performing similar functions) required for same-day electronic delivery of the Exchange Shares.

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<u>Section</u> <u>9.</u> <u>Reserved</u>.

<u>Section</u> <u>10.</u> <u>Covenants</u>. Until such time as no shares of Series N Stock remain outstanding, the Corporation, and as applicable, its Subsidiaries, will at all times comply with the following covenants:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a) The Corporation will timely file on the applicable deadline all reports required to be filed with the Commission pursuant to Sections 13 or 15(d) of the Exchange Act, and will take all reasonable action under its control to ensure that adequate current public information with respect to the Corporation, as required in accordance with Rule 144 of the Securities Act, is publicly available, and will not terminate its status as an issuer required to file reports under the Exchange Act even if the Exchange Act or the rules and regulations thereunder would permit such termination.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b) The Corporation will cause the Common Stock to be listed or quoted for trading on any of NYSE, NYSE American, Nasdaq, CBOE, OTCQB or OTCQX until a Fundamental Transaction.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c) The Corporation shall ensure that, until a Fundamental Transaction, trading in the Common Stock will not be suspended, halted, chilled, frozen, reach zero bid or otherwise cease trading on the Corporation's principal trading market for a period of more than five (5) consecutive Trading Days.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d) The Corporation shall not enter into any agreement or otherwise agree to any covenant, condition, or obligation that locks up, restricts in any way or otherwise prohibits the Corporation from issuing Equity Securities to any Holder or any Affiliate of any Holder pursuant to this Certificate.

The covenants set forth in Section 10(d) will also apply to all Subsidiaries.

<u>Section</u> <u>11.</u> <u>Covenant Default</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a) <u>Event of Default</u>. The Required Holders may elect to declare an "<u>Event of Default</u>" if any of the following conditions or events shall occur and be continuing:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(i) The Corporation or any Subsidiary fails to fully comply with any covenant, obligation or agreement of the Corporation or any Subsidiary in this Certificate (other than payment or issuance defaults which are addressed in subparagraph (ii) below), and such failure, if known to the Required Holders and reasonably possible of cure, is not cured within thirty (30) calendar days following notice to cure from the Required Holders;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(ii) The Corporation fails to pay any amount due and payable to the Holders pursuant to and as required by this Certificate, and such failure, if known to the Holders and reasonably possible of cure, is not cured within five (5) Trading Days following notice of notice to cure from the Required Holders;

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(iii) The Corporation shall (1) apply for or consent to the appointment of, or the taking of possession by, a receiver, custodian, trustee or liquidator; (2) make a general assignment for the benefit of the Corporation's creditors; or (3) commence a voluntary case under the U.S. Bankruptcy Code as now and hereafter in effect, or any successor statute; or

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(iv) a proceeding or case shall be commenced, without the application or consent of the Corporation, in any court of competent jurisdiction, seeking (1) liquidation, reorganization or other relief with respect to it or its assets or the composition or readjustment of its debts, or (2) the appointment of a trustee, receiver, custodian, liquidator or the like of any substantial part of its assets, and, in each case, such proceedings or case shall remain uncontested for 30 days or shall continue undismissed, or an order, judgment or decree approving or ordering any of the foregoing shall be entered and continue unstayed and in effect, for a period of 60 days, if in the United States, or 90 days, if outside of the United States; or an order for relief against the Corporation shall be entered in an involuntary case under any bankruptcy, insolvency, composition, readjustment of debt, liquidation of assets or similar Law of any jurisdiction.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b) <u>Consequences of Events of Default</u>. If an Event of Default has occurred (i) the Required Holders may, by notice to the Corporation (the "<u>Notice of the Forced Redemption</u>"), force the Corporation to redeem all of the issued and outstanding shares of Series N Preferred Stock then held by the Holders for a price equal to (1) the Stated Value of all such shares of Series N Preferred Stock, with such Stated Value to be paid in such number of shares of Common Stock equal to the quotient obtained by dividing the Stated Value by the Exchange Price; <u>plus</u> (2) any and all other amounts (the "<u>Other Amounts</u>") due and payable to the Holders pursuant to this Certificate, with such Other Amounts to be paid in such number of shares of Common Stock equal to the quotient obtained by dividing the Other Amounts by the Exchange Price (with the shares of Common Stock issuable pursuant to aforementioned sub-sections (1) and (2), collectively, the "<u>Forced Redemption Shares</u>"); (ii) the Holders shall have the right to pursue any other remedies that the Required Holders may have under applicable law and/or in equity; and (iii) the Holders shall have the right to seek and receive injunctive relief from a court prohibiting the Corporation from issuing any of its Common Stock or Preferred Stock to any party unless the all shares of Series N Preferred Stock owned by the Holders are redeemed in full simultaneously with such issuance. Notwithstanding the foregoing, Holder will not have the right to force the Corporation to redeem any shares of Series N Preferred Stock and issue any Forced Redemption Shares if: (a) the Stockholder Approval is not obtained; or (b) the issuance of such Forced Redemption Shares would cause such Holder, together with its Affiliates, to beneficially own in excess of the Maximum Percentage immediately after giving effect to the issuance of the Forced Redemption Shares. For the avoidance of doubt, any Forced Redemption Shares that would cause the Holder to exceed the Maximum Percentage shall be held in abeyance and shall not be issued until such time, if ever, as the Holder's right to receive such shares would not result in a violation of the Maximum Percentage.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c) <u>Expenses</u>. In the event that any Holder incurs expenses in the enforcement of its rights hereunder, including but not limited to reasonable attorneys' fees, then the Corporation shall immediately reimburse such Holder the reasonable costs thereof.

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<u>Section</u> <u>12.</u> <u>Miscellaneous</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a) <u>Notices</u>. Any and all notices or other communications or deliveries to be provided by the Holders hereunder shall be in writing and delivered personally, by facsimile, or sent by a nationally recognized overnight courier service, addressed to the Corporation, at the address set forth above Attention: Chief Executive Officer, facsimile number (415) 371-8311, with a copy sent to attention of the Corporation's Chief Financial Officer, facsimile number (415) 371-8311, or such other facsimile number or address as the Corporation may specify for such purposes by notice to the Holders delivered in accordance with this <u>Section</u> <u>12(a)</u>. Any and all notices or other communications or deliveries to be provided by the Corporation hereunder shall be in writing and delivered personally, by facsimile, or sent by a nationally recognized overnight courier service addressed to each record Holder at the facsimile number, or address of such Holder appearing on the books of the Corporation. Any notice or other communication or deliveries hereunder shall be deemed given and effective on the earliest of (i) the time of transmission, if such notice or communication is delivered via facsimile at the facsimile number set forth in this <u>Section</u> <u>12(a)</u> prior to 5:30 p.m. (New York City time) on any Trading Day, (ii) the next Trading Day after the time of transmission, if such notice or communication is delivered via facsimile at the facsimile number set forth in this <u>Section</u> <u>12(a)</u> on a day that is not a Trading Day or later than 5:30 p.m. (New York City time) on any Trading Day, (iii) the second Trading Day following the date of mailing, if sent by U.S. nationally recognized overnight courier service, or (iv) upon actual receipt by the party to whom such notice is required to be given.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b) <u>Governing Law</u>. All questions concerning the construction, validity, enforcement and interpretation of this Certificate shall be governed by and construed and enforced in accordance with the internal laws of the State of Delaware, without regard to the principles of conflict of laws thereof. The rule of construction to the effect that any ambiguities are to be resolved against the drafting party shall not be employed in the interpretation of this Certificate or any amendments thereto. All legal proceedings concerning the interpretation, enforcement and defense of the transactions contemplated by this Certificate (whether brought against a party hereto or its respective Affiliates, directors, officers, stockholders, employees or agents) shall be commenced in the state and federal courts sitting in the State of Delaware (the "<u>Delaware Courts</u>").

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c) <u>Uncertificated Shares</u>. The shares of Series N Preferred Stock shall be uncertificated.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d) <u>Waiver</u>. Any waiver by the Corporation or a Holder of a breach of any provision of this Certificate shall not operate as or be construed to be a waiver of any other breach of such provision or of any breach of any other provision of this Certificate or a waiver by any other Holders. The failure of the Corporation or a Holder to insist upon strict adherence to any term of this Certificate on one or more occasions shall not be considered a waiver or deprive that party (or any other Holder) of the right thereafter to insist upon strict adherence to that term or any other term of this Certificate on any other occasion. Any waiver by the Corporation or a Holder must be in writing.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(e) <u>Severability</u>. If any provision of this Certificate is invalid, illegal or unenforceable, the balance of this Certificate shall remain in effect, and if any provision is inapplicable to any Person or circumstance, it shall nevertheless remain applicable to all other Persons and circumstances. If it shall be found that any interest or other amount deemed interest due hereunder violates the applicable law governing usury, the applicable rate of interest due hereunder shall automatically be lowered to equal the maximum rate of interest permitted under applicable law.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(f) <u>Next Trading Day</u>. Whenever any payment or other obligation hereunder shall be due on a day other than a Trading Day, such payment shall be made or other obligation performed on the next succeeding Trading Day.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(g) <u>Headings</u>. The headings contained herein are for convenience only, do not constitute a part of this Certificate and shall not be deemed to limit or affect any of the provisions hereof.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(h) <u>Status of Exchanged or Redeemed Preferred Stock</u>. Any shares of Series N Preferred Stock that are exchanged, redeemed or otherwise acquired by the Corporation or any of its subsidiaries in accordance with the terms of this Certificate shall be automatically and immediately cancelled and retired and shall not be reissued, sold or transfer as shares of Series N Preferred Stock, and shall resume the status of authorized but unissued shares of preferred stock and the Corporation may thereafter take such appropriate action (without the need for stockholder action) as may be necessary to reduce the authorized number of shares of Series N Preferred Stock accordingly.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(i) <u>Amendment</u>. In addition to any other vote or consent required by the Certificate of Incorporation (including this Certificate) or required by law, any of the provisions, terms, rights, powers, preferences and other terms of the Series N Preferred Stock set forth herein may be amended or waived on behalf of all Holders of Series N Preferred Stock by the affirmative written consent or vote of the Holders of at least a majority of the shares of Series N Preferred Stock then outstanding.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(j) <u>Maximum Percentage</u>. Notwithstanding anything herein to the contrary, in no event may shares of Common Stock be issued to any Holder that would cause such Holder's beneficial ownership to exceed the Maximum Percentage.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(k) <u>No Cash Redemption</u>. Notwithstanding anything herein to the contrary, in no event may the Corporation redeem any shares of Series N Preferred Stock then outstanding by cash.

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RESOLVED, FURTHER, that the chief executive officer, the president, the chief financial officer or any vice-president, and the secretary or any assistant secretary, of the Corporation be and they hereby are authorized and directed to prepare and file this Certificate of Designation of Preferences, Rights and Limitations in accordance with the foregoing resolution and the provisions of Delaware law.

IN WITNESS WHEREOF, the undersigned have executed this Certificate this 9th day of September, 2025.

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| | |
|:---|:---|
| /s/ Lisa A. Conte | /s/ Carol R. Lizak |
| Name: Lisa A. Conte | Name: Carol R. Lizak |
| Title: Chief Executive Officer and President | Title: Chief Financial Officer |

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## Exhibit 10.1

**Exhibit 10.1** 

**SECURITIES PURCHASE AGREEMENT** 

**THIS SECURITIES PURCHASE AGREEMENT** (this "**Agreement**"), is dated as of September 9, 2025, by and among Jaguar Health, Inc., a Delaware corporation (the "**Company**"), and the purchasers listed on the <u>Schedule of Purchasers</u> attached hereto (each, a "**Purchaser**" and collectively, the "**Purchasers**").

**<u>RECITALS</u>**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;A. Subject to the terms and conditions set forth in this Agreement and pursuant to Section 4(a)(2) of the Securities Act of 1933, as amended (the "**Securities Act**"), and Rule 506 promulgated thereunder, the Company desires to issue and sell to each Purchaser, and each Purchaser, severally and not jointly, desires to purchase from the Company, (i) that aggregate number of shares of Series N Perpetual Preferred Stock, par value $0.0001 per share, of the Company (the "**Series N Preferred Stock**") set forth opposite such Purchaser's name in column (4) on the <u>Schedule of Purchasers</u> (which aggregate amount for all Purchasers shall collectively be referred to herein as the "**Preferred Shares**").

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;B. The Series N Preferred Stock has the terms set forth in the Certificate of Designation of Preferences, Rights and Limitations of Series N Perpetual Preferred Stock (the "**Certificate of Designation**") in the form attached hereto as <u>Exhibit A</u>, according to which the Preferred Shares shall be exchangeable for shares of Common Stock (such shares of Common Stock exchanged and/or exchangeable from the Preferred Shares, the "**Exchange Shares**").

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;C. The Preferred Shares and the Exchange Shares are collectively referred to herein as the "**Securities.**"

**<u>AGREEMENT</u>**

**NOW, THEREFORE**, in consideration of the mutual agreements, covenants, representations and warranties contained in this Agreement, and for other good and valuable consideration, the receipt and adequacy of which are hereby acknowledged, the Company and each Purchaser hereby agree as follows:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;1. <u>PURCHASE AND SALE OF PREFERRED SHARES.</u>

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a. <u>Sale and Issuance of Stock</u>. Subject to the satisfaction (or waiver) of the terms and conditions set forth in <u>Section</u> <u>4</u> below, the Company agrees to sell to each Purchaser, and each Purchaser, severally and not jointly, agree to purchase from the Company on the Closing Date (as defined below), the number of Preferred Shares as is set forth opposite such Purchaser's name in column (4) on the <u>Schedule of Purchasers</u>, with each Preferred Share having the rights, preferences, and privileges set forth in the Certificate of Designation (the "**Closing**")

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;b. <u>Closing</u>. The date and time of the Closing (the "**Closing Date**") shall be 9:00 a.m., New York City time, on September 10, 2025 (or such later date and time as is mutually agreed to by the Company and each Purchaser) after notification of satisfaction or waiver of the conditions to the Closing set forth in <u>Section</u> <u>4</u> below at the offices of Reed Smith LLP, 1841 Page Mill Road, Suite 110, Palo Alto, California, 94304.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;c. <u>Consideration for Purchase of the Preferred Shares</u>. In consideration of the purchase of the Preferred Shares, each Purchaser agrees to pay an aggregate purchase price at the Closing (the "**Purchase Price**") as set forth in Column (6) on the <u>Schedule of Purchasers</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;d. <u>Form of Payment</u>. On the Closing Date, (i) each Purchaser shall pay its Purchase Price to the Company for the Preferred Shares to be issued and sold to such Purchaser at the Closing, by wire transfer of immediately available funds in accordance with the Company's written wire instructions, and (ii) the Company shall deliver to each Purchaser the Preferred Shares which such Purchaser is then purchasing hereunder, in each case, duly executed or authenticated on behalf of the Company and registered in the name of such Purchaser or its designee, on the applicable balance account held by the Company. Upon the request of a Purchaser, the Company shall provide such Purchaser with a copy of such Purchaser's balance account.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2. <u>COMPANY'S REPRESENTATIONS AND WARRANTIES</u>.

The Company hereby represents and warrants to each Purchaser as of the date of this Agreement and as of the Closing as follows, subject to the exceptions as are disclosed prior to the date of this Agreement in the Company's reports, schedules, forms, statements and other documents required to be filed by the Company under the Securities Act and the Securities Exchange Act of 1934, as amended (the "**Exchange Act**"), including pursuant to Section 13(a) or 15(d) thereof (the foregoing materials, including the exhibits thereto and documents incorporated by reference therein, being collectively referred to herein as the "**SEC Reports**"), which SEC Reports as filed prior to the date of this Agreement shall be deemed a part hereof and shall qualify any representation or warranty otherwise made herein to the extent of the disclosure contained in the SEC Reports as filed prior to the date of this Agreement:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a. <u>Organization, Good Standing and Qualification</u>. The Company is a corporation duly organized and validly existing under the laws of the State of Delaware. The Company has all requisite corporate power and authority to own and operate its properties and assets, to execute and deliver this Agreement and sell the Securities, and to carry out the provisions of this Agreement and to carry on its business as presently conducted. The Company is duly qualified and is authorized to do business and is in good standing as a foreign corporation in all jurisdictions in which the nature of its activities and of its properties (both owned and leased) makes such qualification necessary, except for those jurisdictions in which failure to do so would not have a material adverse effect on the Company or its business (a "**Material Adverse Effect**").

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;b. <u>Authorization; Binding Obligations</u>. Except for the Stockholder Approval (as defined below) which will be sought by the Company after the Closing pursuant to <u>Section</u> <u>4(a)</u>, all corporate action on the part of the Company, its officers, directors and stockholders necessary for the authorization of this Agreement and each of the other agreements entered into by the parties hereto in connection with the transactions contemplated by this Agreement, if any (collectively, the "**Transaction Documents**"), the performance of all obligations of the Company thereunder at the Closing, and the sale, issuance and delivery of the Securities pursuant hereto has been taken or will be taken prior to the Closing.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;c. <u>No Conflict</u>. Neither the execution and delivery of this Agreement, nor the consummation of the transactions contemplated hereby, will (i) violate or result in a breach of or constitute a default under any contract or agreement to which the Company is a party or by which it is bound, (ii) conflict with or result in a breach of or constitute a default under any provision of the certificate of incorporation or bylaws (or other charter documents) of the Company, or (iii) violate or result in a breach of or constitute a default under any judgment, order, decree, rule or regulation of any court or governmental agency to which the Company is subject, except, in the case of clauses (i) and (iii) above, for any such conflict, breach, violation or default that would not, individually or in the aggregate, have a Material Adverse Effect.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;d. <u>SEC Reports; Financial Statements</u>. The Company has filed all SEC Reports required to be filed by the Company under the Securities Act and the Exchange Act, including pursuant to Section 13(a) or 15(d) thereof, for the two years preceding the date of this Agreement (or such shorter period as the Company was required by law or regulation to file such material). The financial statements of the Company included in the SEC Reports comply in all material respects with applicable accounting requirements and the rules and regulations of the U.S. Securities and Exchange Commission (the "**Commission**") with respect thereto as in effect at the time of filing. Such financial statements have been prepared in accordance with United States generally accepted accounting principles applied on a consistent basis during the periods involved ("**GAAP**"), except as may be otherwise specified in such financial statements or the notes thereto and except that unaudited financial statements may not contain all footnotes required by GAAP, and fairly present in all material respects the financial position of the Company as of and for the dates thereof and the results of operations and cash flows for the periods then ended, subject, in the case of unaudited statements, to normal, immaterial, year-end audit adjustments.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;e. <u>Capitalization</u>. Except as set forth on <u>Schedule 2.e.</u>, the authorized capital stock of the Company and the issued and outstanding securities of the Company are as disclosed as of the date of this Agreement in the SEC Reports.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;f. <u>Absence of Litigation</u>. Except as disclosed in the SEC Reports, neither the Company nor any of its directors is engaged in any litigation, administrative, mediation or arbitration proceedings or other proceedings or hearings before any statutory or governmental body, department, board or agency and is not the subject of any investigation, inquiry or enforcement proceedings by any governmental, administrative or regulatory body that could reasonably be expected to have a Material Adverse Effect. No such proceedings, investigation or inquiry are pending or, to the Company's knowledge, threatened against the Company, and, to the Company's knowledge, there are no circumstances likely to give rise to any such proceedings.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;g. <u>Intellectual Property</u>. The Company has, or has rights to use, all patents, patent applications, trademarks, trademark applications, service marks, trade names, trade secrets, inventions, copyrights, licenses and other intellectual property rights and similar rights as described in the SEC Reports as necessary or required for use in connection with its business and which the failure to so have could have a material adverse effect (collectively, the "**Intellectual Property Rights**"). The Company has not received a notice (written or otherwise) that any of the Intellectual Property Rights has expired, terminated or been abandoned, or is expected to expire or terminate or be abandoned, within two (2) years from the date of this Agreement. To the knowledge of the Company, all such Intellectual Property Rights are enforceable and there is no existing infringement by another Person of any of the Intellectual Property Rights.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;h. <u>Issuance of Securities</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;i. The Preferred Shares have been duly authorized and, upon issuance in accordance with the terms hereof and payment of the Purchase Price, shall be validly issued, fully paid and non-assessable and free from all preemptive or similar rights and free of restrictions on transfer other than restrictions on transfer under this Agreement and under applicable state and federal securities laws. Upon exchange of the Preferred Shares in accordance with the Certificate of Designation, the Exchange Shares will be validly issued, fully paid and non-assessable and free from all preemptive or similar rights and free of restrictions on transfer other than restrictions on transfer under this Agreement and under applicable state and federal securities laws.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;3. <u>PURCHASER'S REPRESENTATIONS AND WARRANTIES</u>.

Each Purchaser, for itself and for no other Purchaser, represents and warrants as of the Closing as follows:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a. <u>Organization and Good Standing</u>. If such Purchaser is an entity, such Purchaser is a corporation, partnership, limited liability company or other entity duly incorporated or organized, validly existing and in good standing under the laws of the jurisdiction of its incorporation or organization.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;b. <u>Requisite Power and Authority</u>. Such Purchaser has all necessary power and authority under all applicable provisions of law to execute and deliver the Transaction Documents to which such Purchaser is a party and to purchase the Securities being sold to it hereunder. If such Purchaser is an entity, the execution, delivery and performance of the Transaction Documents to which such Purchaser is a party by such Purchaser and the consummation by it of the transactions contemplated hereby and thereby have been duly authorized by all necessary corporate, limited liability company or partnership action, and no further consent or authorization of such Purchaser or its board of directors, stockholders, partners or similar body, as the case may be, is required. The Transaction Documents to which such Purchaser is a party have been duly authorized, executed and delivered by such Purchaser and assuming due authorization, execution and delivery by the Company, constitute valid and binding obligations of such Purchaser enforceable against such Purchaser in accordance with the terms thereof, except as such enforceability may be limited by general principles of equity or applicable bankruptcy, insolvency, reorganization, moratorium, liquidation or similar laws relating to, or affecting generally, the enforcement of applicable creditors' rights and remedies.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;c. <u>No Public Sale or Distribution</u>. Such Purchaser is acquiring the Preferred Shares, and upon exchange of the Preferred Shares will acquire the Exchange Shares, for its own account and not with a view towards, or for resale in connection with, the public sale or distribution thereof, except pursuant to sales registered or exempted under the Securities Act; *provided, however*, that by making the representations herein, such Purchaser does not agree to hold any of the Securities for any minimum or other specific term and reserves the right to dispose of all or any part of the Securities at any time in accordance with or pursuant to a registration statement or an exemption from registration under the Securities Act and pursuant to the applicable terms of the Transaction Documents. Such Purchaser is acquiring the Securities hereunder in the ordinary course of its business. Such Purchaser does not presently have any agreement or understanding, directly or indirectly, with any Person to distribute any of the Securities. As used in this Agreement, "**Person**" means an individual, a limited liability company, a partnership, a joint venture, a corporation, a trust, an unincorporated organization and a government or any department or agency thereof.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;d. <u>Accredited Investor Status</u>. Such Purchaser is an "accredited investor" as that term is defined in Rule 501(a) of Regulation D. Such Purchaser has executed and delivered to the Company a questionnaire in substantially the form attached hereto as <u>Exhibit B</u> (the "**Investor Questionnaire**"), which such Purchaser represents and warrants is true, correct and complete. Such Purchaser will promptly notify the Company of any changes to its status as an "accredited investor".

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;e. <u>Reliance on Exemptions</u>. Such Purchaser understands that the Securities are being offered and sold to it in reliance on specific exemptions from the registration requirements of United States federal and state securities laws and that the Company is relying upon the truth and accuracy of, and such Purchaser's compliance with, the representations, warranties, agreements, acknowledgments and understandings of such Purchaser set forth in the Transaction Documents and the Investor Questionnaire in order to determine the availability of such exemptions and the eligibility of such Purchaser to acquire the Securities.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;f. <u>Information</u>. Such Purchaser and its advisors, if any, have had an opportunity to discuss the Company's business, management and financial affairs with the Company's management and to obtain any additional information which such Purchaser has deemed necessary or appropriate for conducting its due diligence investigation and deciding whether or not to purchase the Securities, including an opportunity to receive, review and understand the information regarding the Company's financial statements, capitalization and other business information contained in the SEC Reports as such Purchaser deems prudent. Such Purchaser has sufficient knowledge and experience in investing in companies similar to the Company so as to be able to evaluate the risks and merits of its investment in the Company. Such Purchaser acknowledges that no representations or warranties, oral or written, have been made by the Company or any agent thereof except as set forth in this Agreement. Such Purchaser understands that its investment in the Securities involves a high degree of risk and represents and warrants that it is able to bear the economic risk and complete loss of such investment. Such Purchaser has sought such accounting, legal and tax advice as it has considered necessary to make an informed investment decision with respect to its acquisition of the Securities.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;g. <u>No Governmental Review</u>. Such Purchaser understands that no United States federal or state agency or any other government or governmental agency has passed on or made any recommendation or endorsement of the Securities or the fairness or suitability of the investment in the Securities nor have such authorities passed upon or endorsed the merits of the offering of the Securities.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;h. <u>Transfer or Resale</u>. Such Purchaser understands that, except as provided in <u>Section</u> <u>7</u>: (i) the Securities have not been and are not being registered under the Securities Act or any state securities laws, and may not be offered for sale, sold, assigned or transferred unless (A) subsequently registered thereunder, or (B) such Purchaser shall have delivered to the Company an opinion of counsel, in a form reasonably acceptable to the Company, to the effect that such

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Securities to be sold, assigned or transferred may be sold, assigned or transferred pursuant to Rule 144, as amended, promulgated under the Securities Act (or a successor rule thereto) ("**Rule 144**") or an exemption from such registration, (ii) any sale of the Securities made in reliance on Rule 144 may be made only in accordance with the terms of Rule 144 and further, if Rule 144 is not applicable, any resale of the Securities under circumstances in which the seller (or the Person through whom the sale is made) may be deemed to be an underwriter (as that term is defined in the Securities Act) may require compliance with some other exemption under the Securities Act or the rules and regulations of the Commission thereunder, and (iii) neither the Company nor any other Person is under any obligation to register the Securities under the Securities Act or any state securities laws or to comply with the terms and conditions of any exemption thereunder.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;i. <u>Legends</u>. Such Purchaser understands that the certificates or other instruments representing the Securities, including any applicable balance account at Equiniti Trust Company, LLC, the Company's transfer agent (the "**Transfer Agent**"), except as set forth below, shall bear any legend as required by the "blue sky" laws of any state and a restrictive legend in substantially the following form (and a stop-transfer order may be placed against transfer of such Securities):

NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH ANY OF THESE SECURITIES ARE CONVERTIBLE OR EXCHANGEABLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR THE SECURITIES UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR (B) AN OPINION OF COUNSEL, IN A FORM REASONABLY ACCEPTABLE TO THE COMPANY, THAT REGISTRATION IS NOT REQUIRED UNDER SAID ACT.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;j. <u>Legend Removal</u>. Unless otherwise required by state securities laws, the legend set forth above shall be removed and the Company shall issue a certificate without such legend to the holder of the Securities upon which it is stamped or issue to such holder by electronic delivery at the applicable balance account at The Depository Trust Company ("**DTC**") or the Transfer Agent, as applicable, and at the Purchaser's election so long as the Purchaser is not an affiliate of the Company, if (i) such Securities are registered for resale under the Securities Act, (ii) in connection with a sale, assignment or other transfer, such holder provides the Company with an opinion of a law firm reasonably acceptable to the Company, in a form reasonably acceptable to the Company, to the effect that such sale, assignment or transfer of the Securities may be made without registration under the applicable requirements of the Securities Act, or (iii) such holder provides the Company with an opinion of a law firm reasonably acceptable to the Company, in a form reasonably acceptable to the Company, to the effect that the Securities can be sold, assigned or transferred pursuant to Rule 144 or an exemption from registration.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;k. <u>No Conflicts</u>. The execution, delivery and performance by such Purchaser of the Transaction Documents and the consummation by such Purchaser of the transactions contemplated hereby and thereby will not (i) result in a violation of the organizational documents of such Purchaser, (ii) conflict with, or constitute a default (or an event which with notice or lapse of time or both would become a default) under, or give to others any rights of termination, amendment, acceleration or cancellation of, any agreement, indenture or instrument to which such Purchaser is a party, or (iii) result in a violation of any law, rule, regulation, order, judgment or decree (including federal and state securities laws) applicable to such Purchaser, except in the case of clauses (ii) and (iii) above, for such conflicts, defaults, rights or violations which would not, individually or in the aggregate, reasonably be expected to have a material adverse effect on the ability of such Purchaser to perform its obligations hereunder.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;l. <u>No General Solicitation and Advertising</u>. Such Purchaser is not, to such Purchaser's knowledge, purchasing the Securities as a result of any advertisement, article, notice or other communication regarding the Securities published in any newspaper, magazine or similar media or broadcast over television or radio or presented at any seminar or any other general solicitation or general advertisement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;m. <u>Residency</u>. Such Purchaser is a resident of that jurisdiction specified in its address on the <u>Schedule of Purchasers</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;n. <u>Brokers</u>. There is no broker, investment banker, financial advisor, finder or other Person which has been retained by or is authorized to act on behalf of such Purchaser who might be entitled to any fee or commission for which the Company will be liable in connection with the execution of this Agreement and the consummation of the transactions contemplated hereby.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;o. <u>Foreign Assets Control Regulations, Etc</u>. Neither such Purchaser, any of its affiliates or beneficial owners, nor any person for whom such Purchaser is acting as agent or nominee, (i) appears on the list of Specially Designated Nationals and Blocked Persons ("**SDN List**") maintained by the Office of Foreign Assets Control of the U.S. Treasury Department ("**OFAC**"), the list of Foreign Sanctions Evaders maintained by OFAC, or any other lists of restricted parties maintained by the U.S. Government, nor are they otherwise a party with which any entity is prohibited to deal under the laws of the United States, (ii) is directly or indirectly owned, individually or in aggregate, 50% or more by one or more persons on the SDN List, (iii) is a senior foreign political figure or any immediate family member or close associate of a senior foreign political figure or (iv) is identified as a terrorist organization on any other relevant lists maintained by governmental authorities. Such Purchaser further represents and warrants that this Agreement and any related transactions are not designed or intended to evade or circumvent any applicable regulations related to or oversight by the Committee on Foreign Investment in the United States ("**CFIUS**"). Such Purchaser further represents and warrants that it: (1) has conducted thorough due diligence with respect to all of its beneficial owners, (2) has established the identities of all beneficial owners and the source of each of the beneficial owner's funds and (3) shall retain evidence of any such identities, any such source of funds and any such due diligence.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;p. <u>Regulation M</u>. Such Purchaser is aware that the anti-manipulation rules of Regulation M under the Exchange Act may apply to sales of the Securities and other activities with respect to the Common Stock by such Purchaser.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;q. <u>Representations and Warranties of the U.K. Investors</u>. If and only if the Such Purchaser is a resident of the United Kingdom, then such Purchaser further represents and warrants as of the Closing as follows:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(A) Such Purchaser and any person acting on its behalf falls within Article 19(5) and/or 49(2) of the Financial Services and Markets Act (Financial Promotion) Order 2005, as amended, and undertakes that it will acquire, hold, manage and (if applicable) dispose of any Securities purchased by it for the purposes of its business only.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(B) The allocation, allotment, issue and delivery to such Purchaser, or the person specified by such Purchaser for registration as holder, of the Securities will not give rise to a stamp duty or stamp duty reserve tax liability under (or at a rate determined under) any of sections 67, 70, 93 or 96 of the Finance Act 1986 (depository receipts and clearance services) and that such Purchaser is not purchasing the Securities as nominee or agent for any person or persons to whom the allocation, allotment, issue or delivery of the Securities would give rise to such a liability.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(C) Such Purchaser has complied with and will comply with all applicable laws and regulations with respect to anything done by such Purchaser or on its behalf in relation to the Securities (including all relevant provisions of the Financial Services and Markets Act 2000 and the Financial Services Act 2021 in respect of anything done in, from or otherwise involving the United Kingdom and all relevant provisions of MAR).

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(D) (i) Such Purchaser has complied with its obligations under the Criminal Justice Act 1993 and MAR; (ii) in connection with money laundering and terrorist financing, such Purchaser has complied with its obligations under the Proceeds of Crime Act 2002 (as amended), the Terrorism Act 2000 (as amended), the Terrorism Act 2006 and the Money Laundering Regulations 2007; and (iii) such Purchaser is not a person: (a) with whom transactions are prohibited under the Foreign Corrupt Practices Act of 1977 or any economic sanction programmes administered by, or regulations promulgated by, the Office of Foreign Assets Control of the U.S. Department of the Treasury; (b) named on the Consolidated List of Financial Sanctions Targets maintained by HM Treasury of the United Kingdom; or (c) subject to financial sanctions imposed pursuant to a regulation of the European Union or a regulation adopted by the United Nations (together, the Regulations); and, if making payment on behalf of a third party, that satisfactory evidence has been obtained and recorded by it to verify the identity of the third party as required by the Regulations and such Purchaser has obtained all governmental and other consents (if any) which may be required for the purpose of, or as a consequence of, such subscription.

If at any time during the term of this Agreement, the representations and warranties set forth in this <u>Section</u> <u>3</u> cease to be true, such Purchaser shall promptly so notify the Company in writing.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;4. <u>COVENANTS</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a. <u>Stockholder Approval</u>. The Company shall use commercially reasonable efforts to file a preliminary proxy statement with the Commission for the purpose of obtaining such approvals as may be required by the Certificate of Designation and the applicable rules and regulations of the Nasdaq Stock Market (or any successor entity) from the stockholders of the Company with respect to (i) the issuance of (x) the Exchange Shares issuable upon exchange of the Preferred Shares and (y) the shares of Common Stock issuable upon redemption of the Preferred Shares pursuant to the terms of the Certificate of Designation, collectively, in excess of 19.99% of the issued and outstanding Common Stock on the date of this Agreement (the "**Exchange Cap**"), and (ii) any other applicable rule or regulation of the Nasdaq Stock Market (or any successor entity) from the stockholders of the Company with respect to the issuance of all Exchange Shares (collectively, the "**Stockholder Approval**"). The Company shall use commercially reasonable efforts to hold a meeting of its stockholders at the earliest practical date after the date of this Agreement but in no event later than ninety (90) days after the Closing for the purpose of obtaining the Stockholder Approval, with the recommendation of the Company's board of directors (the "**Board of Directors**") that such proposals are approved, and the Company shall solicit proxies from its stockholders in connection therewith in the same manner as all other management proposals in such proxy statement and all management-appointed proxyholders shall vote their proxies in favor of such proposal. If the Company does not obtain Stockholder Approval at the first meeting held for such purpose, upon the written request of holders of Preferred Shares representing at least a majority of the amount of the outstanding Preferred Shares, the Company shall use commercially reasonable efforts to call another meeting of stockholders within four (4) months of the first meeting of stockholders held pursuant to this <u>Section</u> <u>4(a)</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;b. The Purchaser, in his/her/its capacity as the holder of one of the 6% convertible promissory notes issued by the Company on June 24, 2025 (the "<u>Notes</u>") pursuant to that certain Note Exchange and Warrant Purchase Agreement, dated as of June 24, 2025, by and between the Company and the buyers named therein (the "<u>Note Exchange Agreement</u>"), hereby acknowledges and consents to, notwithstanding anything to the contrary in the Notes and/or the Note Exchange Agreement, the use of proceeds from the transactions contemplated by this Agreement by the Company at its sole discretion, including but not limited to, repayment of the Notes.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;5. <u>CONDITIONS TO CLOSING</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a. <u>Conditions to Each Purchaser's Obligation to Purchase</u>. The obligation of each Purchaser to consummate the transactions contemplated in the Transaction Documents at the Closing is subject to the satisfaction on or before the date of the Closing of the following conditions, all or any of which may be waived in writing by such Purchaser as to its obligation to consummate the transactions so contemplated:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;i. <u>Performance</u>. The Company shall have (A) filed the Certificate of Designation with the Secretary of State of the State of Delaware and (B) duly executed and delivered to such Purchaser (i) each of the Transaction Documents and (ii) the Preferred Shares purchased by such Purchaser at the Closing pursuant to this Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;ii. <u>Proceedings</u>. All corporate and other proceedings taken or to be taken in connection with the transactions contemplated hereby to be consummated at or prior to the Closing and all documents incidental thereto or required to be delivered prior to or at the Closing will be reasonably satisfactory in form and substance to such Purchaser.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;iii. <u>Suits/Proceedings</u>. No action, suit, proceeding or investigation by or before any court, administrative agency or other governmental authority shall have been instituted or threatened to restrain, prohibit or invalidate the transactions contemplated by this Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;iv. <u>Authorization of Issuance</u>. The Board of Directors will have authorized the issuance and sale of the Securities by it to the Purchasers pursuant to this Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;v. <u>Consents and Approvals</u>. The Company shall have obtained any and all consents (including all governmental or regulatory consents, approvals or authorizations required in connection with the valid execution and delivery of this Agreement), permits and waivers, other than the Stockholder Approval, that are necessary or appropriate for consummation of the transactions contemplated by this Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;vi. <u>Representations and Warranties</u>. The representations and warranties of the Company contained in this Agreement that are not qualified by materiality or similar qualification shall be true and correct in all material respects on and as of the Closing, except to the extent expressly made as of an earlier date, in which case such representations and warranties shall be true and correct in all material respects as of such earlier date, and the representations and warranties of the Company contained in this Agreement that are qualified by materiality or similar qualification shall be true and correct in all respects on and as of the Closing, except to the extent expressly made as of an earlier date, in which case such representations and warranties shall be true and correct in all respects as of such earlier date.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;b. <u>Conditions to the Company</u><u>'</u><u>s Obligation to Sell</u>. The obligation of the Company to consummate the transactions contemplated herein at the Closing is subject to the satisfaction on or before the date of the Closing of the following conditions, all or any of which may be waived in writing by the Company as to its obligation to consummate the transaction so contemplated:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;i. <u>Performance</u>. Each Purchaser shall have executed each of the Transaction Documents to which it is a party and delivered the same to the Company.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;ii. <u>Investor Questionnaire</u>. Each Purchaser shall have executed and delivered to the Company an Investor Questionnaire pursuant to which such Purchaser shall provide information necessary to confirm such Purchaser's status as an "accredited investor" (as such term is defined in Rule 501 promulgated under the Securities Act) and to enable the Company to comply with its obligations under <u>Section</u> <u>7</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;iii. <u>Payment of Purchase Price</u>. Each Purchaser shall have delivered to the Company the Purchase Price for the Preferred Shares being purchased by such Purchaser in the form and manner prescribed under <u>Section</u> <u>1(d)</u> hereof.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;iv. <u>Suits/Proceedings</u>. No action, suit, proceeding or investigation by or before any court, administrative agency or other governmental authority shall have been instituted or threatened to restrain, prohibit or invalidate the transactions contemplated by this Agreement.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;v. <u>Representations and Warranties</u>. The representations and warranties of each Purchaser contained in this Agreement that are not qualified by materiality or similar qualification shall be true and correct in all material respects on and as of the Closing, except to the extent expressly made as of an earlier date, in which case such representations and warranties shall be true and correct in all material respects as of such earlier date, and the representations and warranties of such Purchaser contained in this Agreement that are qualified by materiality or similar qualification shall be true and correct in all respects on and as of the Closing, except to the extent expressly made as of an earlier date, in which case such representations and warranties shall be true and correct in all respects as of such earlier date.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;6. <u>RELIANCE</u>. Each Purchaser is aware that the Company is relying on the accuracy of the representations and warranties set forth in <u>Section</u> <u>3</u> hereof to establish compliance with federal and state securities laws. If any such warranties or representations are not true and accurate in any respect as of the Closing, each Purchaser with such knowledge shall so notify the Company in writing immediately and shall be cause for rescission by the Company at its sole election.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;7. <u>REGISTRATION RIGHTS</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a. The Company hereby agrees that, within thirty (30) days after the Closing Date, the Company shall file a registration statement on Form S-3 (or such other form available, the "**Registration Statement**") with the Commission with respect to the Registrable Securities. The Company shall use its commercially reasonable efforts to cause the Registration Statement to be declared effective under the Securities Act as promptly as possible after the filing thereof, but in no later than (x) the sixtieth (60th) day following the filing of the Registration Statement in the event of "limited review" by the Commission, or (y) the ninetieth (90th) day following the filing of the Registration Statement in the event of a "review" by the Commission, and shall use its commercially reasonable efforts to keep such Registration Statement continuously effective under the Securities Act during the entire Effectiveness Period (as such term is defined below along with any other defined terms used in this <u>Section</u> <u>7</u>).

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;b. If the Commission informs the Company that all of the Registrable Securities cannot be registered for resale as a secondary offering on a single registration statement, the Company will use its best efforts to (i) promptly file amendments to the Registration Statement, as required by the Commission, covering the maximum number of Registrable Securities permitted to be registered by the Commission, on Form S-3 or such other form available to register for resale the Registrable Securities as a secondary offering and (ii) as promptly as allowed by the Commission or the guidance of the Commission provided to the Company or to registrants of securities in general, file one or more additional registration statements on Form S-3 or such other form available to register for resale those Registrable Securities that were not registered for sale on the Registration Statement, as amended.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;c. Notwithstanding anything in this <u>Section</u> <u>7</u> to the contrary, the Company may delay or suspend the effectiveness of the Registration Statement for up to thirty (30) days (a "**Delay Period**") if the Board of Directors determines in good faith that (i) effectiveness of the Registration Statement must be suspended in accordance with the rules and regulations under the Securities Act or that (ii) the disclosure of material non-public information at such time would be detrimental to the Company and its subsidiaries, taken as a whole. Notwithstanding the foregoing, the Company shall use its reasonable best efforts to ensure that the Registration Statement is declared effective and its permitted use is resumed following a Delay Period as promptly as practicable.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;d. All fees and expenses incident to the performance of or compliance with this <u>Section</u> <u>7</u> by the Company shall be borne by the Company whether or not any Registrable Securities are sold pursuant to a Registration Statement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;e. Except for registration rights granted on or prior to the date of this Agreement, the Company has not entered into and, unless agreed in writing by each Holder on or after the date of this Agreement, will not enter into, any agreement or arrangement that (i) is inconsistent with the rights granted to the Holders with respect to Registrable Securities in this Agreement or otherwise conflicts with the provisions hereof in any material respect or (ii) other than as set forth in this Agreement, would allow any holder of the Common Stock or other securities of the Company to include such securities in any Registration Statement filed by the Company on a basis that is more favorable in any material respect to the rights granted to the Holders hereunder, including granting registration rights that would have priority over the Registrable Securities with respect to the inclusion of such securities in any registration.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;f. As used in this <u>Section</u> <u>7</u>, the following terms have the respective meanings:

"**Effectiveness Period**" means, the period commencing on the Registration Statement Effective Date and ending on the earlier of (i) the time as all of the Registrable Securities covered by such Registration Statement have been sold (either pursuant to a Registration Statement or otherwise) by the Holders, or (ii) the time as all of the remaining Registrable Securities are eligible to be sold by the Holders without compliance with the volume limitations or public information requirements of Rule 144.

"**Holder**" or "**Holders**" means the holder or holders, as the case may be, from time to time, of Registrable Securities.

"**Registrable Securities**" means: (i) the Exchange Shares, and (ii) any securities issued or issuable upon any stock split, dividend or other distribution, recapitalization or similar event, or any price adjustment as a result of such stock splits, reverse stock splits or similar events with respect to the securities referenced in (i) and (ii); *provided*, *however*, that, as to any particular Registrable Security, such securities shall cease to be Registrable Securities upon the earliest to occur of: (A) a Registration Statement with respect to the sale of such securities shall have become effective under the Securities Act and such securities shall have been sold, transferred, disposed of or exchanged in accordance with such Registration Statement by the applicable Holder; (B) (i) such securities shall have been otherwise transferred, (ii) new certificates for such securities not bearing (or book entry positions not subject to) a legend restricting further transfer shall have been delivered by the Company and (iii) subsequent public distribution of such securities shall not require registration under the Securities Act; (C) such securities shall have ceased to be outstanding; and (D) such securities may be sold without registration pursuant to Rule 144 or any successor rule promulgated under the Securities Act (but with no volume or other restrictions or limitations including as to manner or timing of sale).

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"**Registration Statement**" means the registration statements required to be filed in accordance with this <u>Section</u> <u>7</u> and any additional registration statements required to be filed under this <u>Section</u> <u>7</u>, including in each case the prospectus, amendments and supplements to such registration statements or prospectus, including pre and post effective amendments, all exhibits thereto, and all material incorporated by reference or deemed to be incorporated by reference therein.

"**Registration Statement Effective Date**" means, as to a Registration Statement, the date on which such Registration Statement is first declared effective by the Commission.

"**Trading Day**" means a day on which the Nasdaq Stock Market is open for trading.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;8. <u>MISCELLANEOUS</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a. <u>Survival</u>. The representations, warranties, covenants and agreements made herein shall survive the Closing for a period of one (1) year.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;b. <u>Successors and Assigns</u>. Except as otherwise expressly provided herein, the provisions hereof shall inure to the benefit of, and be binding upon, the successors, assigns, heirs, executors and administrators of the parties hereto.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;c. <u>Entire Agreement; Amendment</u>. This Agreement and the schedules and exhibits attached hereto constitute the entire agreement and understanding between the parties with respect to the subject matters herein, and supersede and replace any prior agreements and understandings, whether oral or written between and among them with respect to such matters. The provisions of this Agreement may be waived, altered, amended or repealed, in whole or in part, only upon the written consent of the Company and holders of at least 50.1% in interest of the Exchange Shares (either exchanged from the Series N Preferred Stock or exchangeable from the then outstanding Series N Preferred Stock) then outstanding or, in the case of a waiver, by the party against whom enforcement of any such waived provision is sought; provided that if any amendment, modification or waiver disproportionately and adversely impacts a Purchaser (or group of Purchasers), the consent of such disproportionately impacted Purchaser (or group of Purchasers) shall also be required.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;d. <u>Title and Subtitles</u>. The titles of the Sections and subsections of this Agreement are for convenience of reference only and are not to be considered in construing this Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;e. <u>Counterparts</u>. This Agreement may be executed in any number of counterparts, each of which shall be an original, but all of which together shall constitute one instrument. In the event that any signature is delivered by facsimile transmission or by e-mail delivery of a ".pdf" format data file, such signature shall create a valid and binding obligation of the party executing (or on whose behalf such signature is executed) with the same force and effect as if such facsimile or ".pdf" signature page were an original thereof.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;f. <u>Applicable Law</u>. This Agreement shall be governed by and construed in accordance with laws of the State of California, applicable to contracts between California residents entered into and to be performed entirely within the State of California.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;g. <u>Venue</u>. Any action, arbitration, or proceeding arising directly or indirectly from this Agreement or any other instrument or security referenced herein shall be litigated or arbitrated, as appropriate, in the County of San Francisco, in the State of California.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;h. <u>Authority</u>. With respect to each Purchaser, the individual executing and delivering this Agreement on behalf of such Purchaser shall have been duly authorized and be duly qualified to execute and deliver this Agreement in connection with the purchase of the Securities and the signature of such individual shall be binding upon Purchaser.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;i. <u>Notices</u>. All notices and other communications provided for or permitted hereunder shall be made by hand-delivery, electronic mail, telecopier, or overnight air courier guaranteeing next day delivery at the address set forth on the signature page hereof, if to the Company, and on the <u>Schedule of Purchasers</u>, if to a Purchaser, with copies to such Purchaser's representatives as set forth on the <u>Schedule of Purchasers</u>. All such notices and communications shall be deemed to have been duly given (i) at the time delivered by hand, if personally delivered (ii) when sent, if sent my electronic mail (provided that such sent email is kept on file (whether electronically or otherwise) by the sending party and the sending party does not receive an automatically generated message from the recipient's email server that such email could not be delivered to such recipient), (iii) when receipt acknowledged, if telecopied, and (iv) the next business day after timely delivery to the courier, if sent by overnight air courier guaranteeing next day delivery. The parties may change the addresses to which notices are to be given by giving five days prior written notice of such change in accordance herewith.

**[REMAINDER OF PAGE INTENTIONALLY LEFT BLANK]** 

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**IN WITNESS WHEREOF,** the Company and each Purchaser have caused their respective signature page to this Securities Purchase Agreement to be executed as of the date first written above.

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| | | |
|:---|:---|:---|
| **COMPANY:** | **COMPANY:** | <u>Address for Notice</u>: |
| **JAGUAR HEALTH, INC.** | **JAGUAR HEALTH, INC.** | 200 Pine Street, Suite 400<br> San Francisco, CA 94104<br> Fax: (415) 371-8300 |
| By: |  |  |
|  | Name: Lisa A. Conte<br> Title: CEO and President |  |
| With a copy to (which shall not constitute notice):<br>Donald C. Reinke, Esq.<br> Reed Smith LLP<br> 1841 Page Mill Road, Suite 110<br> Palo Alto, CA, 94304 | With a copy to (which shall not constitute notice):<br>Donald C. Reinke, Esq.<br> Reed Smith LLP<br> 1841 Page Mill Road, Suite 110<br> Palo Alto, CA, 94304 |  |

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**[REMAINDER OF PAGE INTENTIONALLY LEFT BLANK** 

**SIGNATURE PAGE FOR PURCHASERS FOLLOW]** 

SIGNATURE PAGE TO SECURITIES PURCHASE AGREEMENT

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**IN WITNESS WHEREOF,** the Company and each Purchaser have caused their respective signature page to this Securities Purchase Agreement to be executed as of the date first written above.

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| | | |
|:---|:---|:---|
| **PURCHASER:** | **PURCHASER:** | <u>Address for Notice</u>: |
| **[PURCHASER'S NAME]** | **[PURCHASER'S NAME]** |  |
| By: |  |  |
|  | Name:<br> Title: |  |

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SIGNATURE PAGE TO SECURITIES PURCHASE AGREEMENT

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**<u>Schedule of Purchasers</u>**

SCHEDULE OF PURCHASERS - SECURITIES PURCHASE AGREEMENT

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**<u>Schedule 2.e.</u>**

<u>Capitalization</u> 

SCHEDULE 2.E. - SECURITIES PURCHASE AGREEMENT

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**<u>EXHIBIT A</u>**

**Certificate of Designation of Preferences, Rights and Limitations of** 

**Series N Perpetual Preferred Stock** 

EXHIBIT A TO SECURITIES PURCHASE AGREEMENT

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**<u>EXHIBIT B</u>**

**Investor Questionnaire** 

EXHIBIT B TO SECURITIES PURCHASE AGREEMENT

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**INVESTOR QUESTIONNAIRE** 

This Investor Questionnaire ("*Questionnaire*") must be completed by each potential investor in connection with the offer and sale of shares of Series N Perpetual Preferred Stock, par value $0.0001 per share (the "*Preferred Stock*") and warrants to acquire the shares of voting common stock, par value $0.0001 per share, of the Company (the "*Common Stock*") (sometimes collectively referred to herein as the "*Securities*"), of Jaguar Health, Inc., a Delaware corporation (the "*Company*"). The Securities are being offered and sold by the Company without registration under the Securities Act of 1933, as amended (the "*Securities Act*"), and the securities laws of certain states, in reliance on the exemptions contained in Section 4(a)(2) of the Securities Act and on Regulation D promulgated thereunder and in reliance on similar exemptions under applicable state laws. The Company must determine that a potential investor meets certain suitability requirements before offering or selling the Securities to such investor. The purpose of this Questionnaire is to assure the Company that each investor will meet the applicable suitability requirements. The information supplied by you will be used in determining whether you meet such criteria, and reliance upon the private offering exemptions from registration is based in part on the information herein supplied.

This Questionnaire does not constitute an offer to sell or a solicitation of an offer to buy any security. By signing this Questionnaire, you represent and warrant that this Questionnaire is true, correct and complete and you will be authorizing the Company to provide a completed copy of this Questionnaire to such parties as the Company deems appropriate in order to ensure that the offer and sale of the Securities will not result in a violation of the Securities Act or the securities laws of any state and that you otherwise satisfy the suitability standards applicable to purchasers of the Securities. All potential investors must answer all applicable questions and complete, date and sign this Questionnaire. Please print or type your responses and attach additional sheets of paper if necessary to complete your answers to any item.

PART A. <u>BACKGROUND INFORMATION</u>

Name of Beneficial Owner of the Securities:<u> </u>

Business Address:<u> </u>

City:<u> </u> State:<u> </u> Zip Code:

Telephone Number:

*If a corporation, partnership, limited liability company, trust or other entity:* 

Type of entity:

State of formation: Approximate Date of formation:<u> </u>

Were you formed for the purpose of investing in the securities being offered? Yes ☐ No ☐

*<u>If an individual</u>:* 

Residence Address: ___________________________________________________________________

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(Number and Street)

City: _________________ State: _____ Zip Code: ___________

Telephone Number: _______________________

Age: _________________ Citizenship: _________ Where registered to vote: _______

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Set forth in the space provided below the state(s), if any, in the United States in which you maintained your residence during the past two years and the dates during which you resided in each state:

Are you a director or executive officer of the Company Yes ☐ No ☐

Social Security or Taxpayer Identification No.: ________________

PART B. <u>ACCREDITED INVESTOR QUESTIONNAIRE</u>

In order for the Company to offer and sell the Securities in conformance with state and federal securities laws, the following information must be obtained regarding your investor status. Please <u>initial each category</u> applicable to you as a purchaser of Securities of the Company.

☐ (1) A bank as defined in Section 3(a)(2) of the Securities Act, or any savings and loan association or other institution as defined in Section 3(a)(5)(A) of the Securities Act whether acting in its individual or fiduciary capacity;

☐ (2) A broker or dealer registered pursuant to Section 15 of the Securities Exchange Act of 1934, as amended (the "*Exchange Act*");

☐ (3) An insurance company as defined in Section 2(a)(13) of the Securities Act;

☐ (4) An investment company registered under the Investment Company Act of 1940 or a business development company as defined in Section 2(a)(48) of that act;

☐ (5) A Small Business Investment Company licensed by the U.S. Small Business Administration under Section 301(c) or (d) of the Small Business Investment Act of 1958;

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| | |
|:---|:---|
| ☐ (6) | A plan established and maintained by a state, its political subdivisions, or any agency or instrumentality of a state or its political subdivisions, for the benefit of its employees, if such plan has total assets in excess of $5,000,000;  |

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| | |
|:---|:---|
| ☐ (7) | An employee benefit plan within the meaning of the Employee Retirement Income Security Act of 1974, if the investment decision is made by a plan fiduciary, as defined in Section 3(21) of such act, which is either a bank, savings and loan association, insurance company or registered investment adviser, or if the employee benefit plan has total assets in excess of $5,000,000 or, if a self-directed plan, with investment decisions made solely by persons that are accredited investors;  |

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☐ (8) A private business development company as defined in Section 202(a)(22) of the Investment Advisers Act of 1940;

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| | |
|:---|:---|
| ☐ (9) | An organization described in Section 501(c)(3) of the Internal Revenue Code, a corporation, Massachusetts or similar business trust, or partnership, not formed for the specific purpose of acquiring the Securities, with total assets in excess of $5,000,000;  |

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| | |
|:---|:---|
| ☐ (10) | A trust, with total assets in excess of $5,000,000, not formed for the specific purpose of acquiring the Securities, whose purchase is directed by a sophisticated person who has such knowledge and experience in financial and business matters that such person is capable of evaluating the merits and risks of investing in the Company;  |

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| | |
|:---|:---|
| ☐ (11) | A natural person whose individual net worth, or joint net worth with that person's spouse, at the time of his purchase exceeds $1,000,000 (exclusive of the value of that person's primary residence)<sup>1</sup>;  |

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| | |
|:---|:---|
| ☐ (12) | A natural person who had an individual income in excess of $200,000 in each of the two most recent years, or joint income with that person's spouse in excess of $300,000, in each of those years (in each case, including foreign income, tax exempt income and full amount of capital gains and losses, but excluding any income of other family members and any unrealized capital appreciation), and has a reasonable expectation of reaching the same income level in the current year;  |

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☐ (13) An executive officer or director of the Company;

☐ (14) An entity in which all of the equity owners qualify under any of the above subparagraphs. If the undersigned belongs to this investor category only, list the equity owners of the undersigned, and the investor category which each such equity owner satisfies.

PART C. <u>BAD ACTOR QUESTIONNAIRE</u>

**1.** **During the past ten years, have you been convicted of any felony or misdemeanor that is related to any securities matter?** 

Yes ☐ (If yes, please continue to Question 1.a)

No ☐ (If no, please continue to Question 2)

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a) If your answer to Question 1 was "yes", was the conviction related to: (i) the purchase or
sale of any security; (ii) the making of any false filing with the Securities and Exchange Commission (the "*SEC* "); <u>or</u> (iii) the conduct of an underwriter, broker, dealer, municipal securities dealer, investment
adviser or paid solicitor of purchasers of securities?

Yes ☐ No ☐

<sup>1</sup> Please follow these guidelines in calculating the value of your principal residence: (i) you may not include equity in your principal residence as an asset; (ii) you may exclude indebtedness that is secured by your primary residence, up to the estimated fair market value of the primary residence on the date hereof from the calculation of liabilities (unless the amount of such indebtedness outstanding on the date hereof exceeds the amount outstanding 60 days before the date hereof, other than as a result of the acquisition of the primary residence, in which case the excess should be included in the calculation of liabilities); and (iii) you should include indebtedness that is secured by your principal residence in excess of the fair market value of the primary residence on the date hereof in the calculation of liabilities. 

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**2.** **Are you subject to any court injunction or restraining order entered during the past five years that is related to any securities matter?** 

Yes ☐ (If yes, please continue to Question 2.a)

No ☐ (If no, please continue to Question 3)

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a) If your answer to Question 2 was "yes", does the court injunction or restraining order currently
restrain or enjoin you from engaging or continuing to engage in any conduct or practice related to: (i) the purchase or sale of any security; (ii) the making of any false filing with the SEC; <u>or</u> (iii) the conduct of an
underwriter, broker, dealer, municipal securities dealer, investment adviser or paid solicitor of purchasers of securities?

Yes ☐ No ☐

**3.** **Are you subject to any final order<sup>2</sup> of any governmental commission, authority, agency or officer<sup>3</sup>(2) related to any securities, insurance or banking matter?** 

Yes ☐ (If yes, please continue to Question 3.a)

No ☐ (If no, please continue to Question 4)

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a) If your answer to Question 3 was "yes":

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;i) Does the order currently bar you from: (i) associating with an entity regulated by such commission,
authority, agency or officer; (ii) engaging in the business of securities, insurance or banking; <u>or</u> (iii) engaging in savings association or credit union activities?

Yes ☐ No ☐

ii) Was the order (i) entered within the past ten years <u>and</u> (ii) based on a violation of any law or regulation that prohibits fraudulent, manipulative or deceptive conduct?

Yes ☐ No ☐

**4.** **Are you subject to any SEC disciplinary order?<sup>4</sup>(3)** 

Yes ☐ (If yes, please continue to Question 4.a)

No ☐ (If no, please continue to Question 5)

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a) If your answer to Question 4 was "yes", does the order currently: (i) suspend or revoke your
registration as a broker, dealer, municipal securities dealer or investment adviser; (ii) place limitations on your activities, functions or operations; <u>or</u> (iii) bar you from being associated with any particular entity or class of
entities or from participating in the offering of any penny stock?

<sup>2</sup> A "final order" is defined under Rule 501(g) as a written directive or declaratory statement issued by a federal or state agency described in Rule 506(d)(1)(iii) under applicable statutory authority that provides for notice and an opportunity for a hearing, and that constitutes a final disposition or action by such federal or state agency. 

<sup>3</sup> You may limit your response to final orders of: (i) state securities commissions (or state agencies/officers that perform a similar function); (ii) state authorities that supervise or examine banks, savings associations or credit unions; (iii) state insurance commissions (or state agencies/officers that perform a similar function); (iv) federal banking agencies; (v) the U.S. Commodity Futures Trading Commission; or (vi) the U.S. National Credit Union Administration. 

<sup>4</sup> You may limit your response to disciplinary orders issued pursuant to Sections 15(b) or 15B(c) of the Exchange Act or Section 203(e) or (f) of the Investment Advisers Act of 1940 (the "*Advisers Act*").

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**5.** **Are you subject to any SEC cease and desist order entered within the past five years?** 

Yes ☐ (If yes, please continue to Question 5.a)

No ☐ (If no, please continue to Question 6)

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a) If your answer to Question 5 was "yes", does the order currently require you to cease and desist
from committing or causing a violation or future violation of (i) any knowledge-based anti-fraud provision of the U.S. federal securities laws<sup>5</sup> <u>or</u> (ii) Section 5 of the
Securities Act?

Yes ☐ No ☐

**6.** **Have you been suspended or expelled from membership in, or suspended or barred from association with a member of, a registered national securities exchange or a registered national or affiliated securities association?** 

Yes ☐ (If yes, please describe the basis of any such suspension or expulsion and any related details in the space provided under Question 10 below)<sup>6</sup>

No ☐ &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(If no, please continue to Question 7)

**7.** **Have you registered a securities offering with the SEC, made an offering under Regulation A or been named as an underwriter in any registration statement or Regulation A offering statement filed with the SEC?** 

Yes ☐ (If yes, please continue to Question 7.a)

No ☐ (If no, please continue to Question 8)

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a) If your answer to Question 7 was "yes":

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;i) During the past five years, was any such registration statement or Regulation A offering statement the subject
of a refusal order, stop order or order suspending the Regulation A exemption?

Yes ☐ No ☐

ii) Is any such registration statement or Regulation A offering statement currently the subject of an investigation or proceeding to determine whether a stop order or suspension order should be issued?

Yes ☐ No ☐

<sup>5</sup> Including (but not limited to) Section 17(a)(1) of the Securities Act, Section 10(b) of the Exchange Act and Rule 10b-5 thereunder, Section 15(c)(1) of the Exchange Act, and Section 206(1) of the Advisers Act or any other rule or regulation thereunder.

<sup>6</sup> In providing additional information, please explain whether or not the suspension or expulsion resulted from "any act or omission to act constituting conduct inconsistent with just and equitable principles of trade."

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**8.** **Are you subject to a U.S. Postal Service false representation order entered within the past five years?** 

Yes ☐ No ☐

**9.** **Are you currently subject to a temporary restraining order or preliminary injunction with respect to conduct alleged by the U.S. Postal Service to constitute a scheme or device for obtaining money or property through the mail by means of false representations?** 

Yes ☐ No ☐

**10.** **In the space provided below, describe any facts or circumstances that caused you to answer "yes" to any Question (indicating the corresponding Question number). Attach additional pages if necessary.** 

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THE UNDERSIGNED UNDERSTANDS THAT THE COMPANY WILL RELY ON THE FOREGOING REPRESENTATIONS TO, AMONG OTHER THINGS, MAINTAIN THE EXEMPTION FOR THE ISSUANCE OF SECURITIES FROM THE REQUIREMENT TO REGISTER SUCH SECURITIES UNDER THE SECURITIES ACT.

The answers to the foregoing questions are correctly stated to the best of my knowledge, information and belief. I hereby agree to notify the Company promptly of any changes in the foregoing information.

**A.** **FOR EXECUTION BY AN INDIVIDUAL:** 

 By:<br>

Print Name:    

Date

**B.** **FOR EXECUTION BY AN ENTITY:** 

Entity Name:    

 By:<br>

Print Name:    

 Title:<br>

Date

**C.** **ADDITIONAL SIGNATURES (if required by partnership, corporation or trust document):** 

Entity Name:    

 By:<br>

Print Name:    

 Title:<br>

Date

Entity Name:    

 By:<br>

Print Name:    

 Title:<br>

Date