Company: XXII
Filing Date: 2025-12-19
Form Type: PRE 14A
Source: 0001493152-25-028573
Chunk: 23

Company: 22nd Century Group, Inc.
Filing Date: 2025-12-19
Form: PRE 14A
Chunk 23
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 addition, If stockholder approval is not obtained, the holders may require us to redeem the Series A Preferred at the Stated Value per share for cash. If approved, the Series A Preferred will be dilutive to current stockholders.

| Our Board of Directors recommends that the stockholders vote “FOR” Proposal 2 to             
 approve the issuance of shares upon the anti-dilution adjustments in the Series A Preferred. |

| PROXY STATEMENT | 16 |

<div align='center'>Proposal THREE:

APPROVAL OF THE ANTI-DILUTION ADJUSTMENTS in the AUGUST WARRANTS</div>

The board of directors has approved and recommends to the stockholders a proposal to approve the amendment to the August 2025 Warrants adding anti-dilution provisions pursuant to Rule 5635(d) of the Nasdaq Stock Market for the potential issuance of more than 19.99% of our outstanding common stock at below the Minimum Price under Nasdaq rules.

General

As previously disclosed on a current report on Form 8-K filed with SEC on August 25, 2025, we sold shares of Series A Preferred and warrants to purchase shares of Common Stock pursuant to a registered direct offering. The investors purchased approximately $10.65 million of shares of Series A Preferred and warrants.9,460,661 of the warrants are currently exercisable at an exercise price of $1.97 per share of common stock and 567,641 of the warrants, issued as placement agent warrants in the offering, are currently exercisable for $2.167 and all of the warrants expire on the date that is five (5) years after issuance. On December 17, 2025, we entered into an amendment to add an anti-dilution provision in the event of any dilutive issuances of our common stock, subject to stockholder approval. Section 3(b) of the warrant amendment provides as follows:

“(b) Subsequent Equity Sales. Following the Stockholder Approval Date, if the Company or any Subsidiary thereof, as applicable, at any time while this Warrant is outstanding, shall sell, enter into an agreement to sell or grant any option to purchase, or sell or grant any right to reprice, or otherwise dispose of or issue (or announce any offer, sale, grant or any option to purchase or other disposition) any Common Stock or Common Stock Equivalents, at an effective price per share less than the Exercise Price then in effect (such lower price, the “Base Share