SECURITIES
PURCHASE AGREEMENT


 


This Securities Purchase
Agreement (this “Agreement”) is made and entered into as of May 15, 2012 by and among 22nd Century Group, Inc.,
a Nevada corporation (the “Company”), and the purchaser(s) identified on the signature pages hereto (each a
“Purchaser” and collectively, the “Purchasers”).


 


WHEREAS, subject
to the terms and conditions set forth in this Agreement and pursuant to Section 4(2), Section 4(6), and Regulation S of the Securities
Act of 1933, as amended (the “Securities Act”), and Rule 506 of Regulation D promulgated thereunder, the Company
desires to offer, issue and sell to the Purchasers (the “Offering”), and the Purchasers, severally and not jointly,
desire to purchase from the Company, in the aggregate, up to Three Million Five Hundred Thousand (3,500,000) shares of the Company’s
common stock, par value $0.00001 per share (the “Common Stock”) at a purchase price of $0.60 per share of Common
Stock (the “Purchase Price”);


 


WHEREAS,
each Purchaser shall also receive five-year warrants to purchase an equal number of shares of
Common Stock as such Purchaser purchases pursuant to this Agreement (the “Warrants”), with such Warrants having
an exercise price equal to One Dollar ($1.00) per share of Common Stock; and


 


WHEREAS, for
purposes of this Agreement, the Common Stock, the Warrants and the shares of Common Stock into which the Warrants are exercisable
being hereinafter collectively referred to as the “Securities”.


 


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


 


		A.	Purchase and Sale



 


(1)          The
introductory paragraphs of this Agreement are hereby incorporated into this Agreement as if fully set forth herein. Subject to
the terms and conditions set forth in this Agreement, at the Closing the Company shall issue and sell to each Purchaser, and each
Purchaser shall, severally and not jointly, purchase from the Company, the number of shares of Common Stock and number of Warrants
set forth on such Purchaser’s signature page to this Agreement. The Closing shall take place at the offices of Foley &
Lardner LLP, One Independent Drive, Suite 1300, Jacksonville, FL 32202, on the Closing Date or
at such other location or time as the parties may agree (the “Closing”). “Closing Date”
means the business day on which all of the conditions set forth in Sections H(1) and H(2) hereof are satisfied or waived, or such
other date as the parties may mutually agree in writing.


 


(2)          Prior
to or at the Closing, each Purchaser shall deliver or cause to be delivered to the Company the aggregate purchase price for the
Common Stock and Warrants to be purchased by such Purchaser as set forth on the signature page of such Purchaser hereto (the “Investment
Amount”). Wire transfer instructions are set forth on Schedule A attached hereto. Such funds will be held for
the Purchaser’s benefit, and will be returned promptly, without interest or setoff, if this Agreement is not accepted by
the Company, or the Offering is terminated pursuant to its terms by the Company.


 



    	 



    	 



    

 


(3)          At the
Closing, the Company shall deliver to the Purchasers a certificate stating that the representations and warranties made by the
Company in Section C of this Agreement were true and correct in all material respects when made and are true and correct in all
material respects on the Closing Date relating to the Securities purchased pursuant to this Agreement as though made on and as
of such Closing Date (provided, however, that representations and warranties that speak as of a specific date shall continue to
be true and correct as of the Closing with respect to such date). The foregoing obligations of the Company shall be conditions
precedent to each Purchaser’s obligation to complete the purchase of the Securities as contemplated by this Agreement.


 


(4)          Each
Purchaser acknowledges and agrees that the purchase of the Securities by such Purchaser pursuant to the Offering is subject to
all the terms and conditions set forth in this Agreement.


 


(5)          The
Purchaser understands and agrees that the Company in its sole discretion reserves the right to accept or reject this or any other
subscription for Securities, in whole or in part, notwithstanding prior receipt by the Purchaser of notice of acceptance of this
subscription. The Company shall have no obligation hereunder until the Company shall execute and deliver to the subscriber an executed
copy of this Agreement. If this subscription is rejected in whole, or the Offering is terminated, all funds received from the Purchaser
will be returned without interest or offset, and this Agreement shall thereafter be of no further force or effect. If this subscription
is rejected in part, the funds for the rejected portion of such subscription will be returned without interest or offset, and this
Agreement will continue in full force and effect to the extent this subscription was accepted.


 


		B.	Representations and Warranties of the Purchaser



 


Each Purchaser, severally
and not jointly, hereby represents and warrants to the Company as of the date hereof and as of the Closing Date, and agrees with
the Company as follows:


 


(1)          The
Purchaser has carefully read this Agreement, the term sheet attached hereto as Exhibit A (the “Term Sheet”)
and the form of Warrant attached hereto as Exhibit B (collectively the “Offering Documents”), and is
familiar with and understands the terms of the Offering, and the Purchaser also acknowledges having access to and reviewed or had
the opportunity to access and review all of the information regarding the Company that is publicly available on the EDGAR database
of the United States Securities and Exchange Commission (“SEC”), including but not limited to portions of the
Company’s publicly available documents which consist of the financial statements included therein and the sections therein
entitled “Risk Factors” and “Our Business” (collectively, the “Publicly Available Information”).
The Purchaser fully understands all of the risks related to the purchase of the Securities. The Purchaser has carefully considered
and has discussed, or has the opportunity to discuss, with the Purchaser’s professional legal, tax, accounting and financial
advisors, to the extent the Purchaser has deemed necessary, the suitability of an investment in the Securities for the Purchaser’s
particular tax and financial situation and has determined that the Securities being purchased by the Purchaser are a suitable investment
for the Purchaser. The Purchaser recognizes that an investment in the Securities involves substantial risks, including the possible
loss of the entire amount of such investment. The Purchaser further recognizes that the Company has broad discretion concerning
the use and application of the proceeds from the Offering.


 



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(2)          The
Purchaser acknowledges that (i) the Purchaser has had the opportunity to request copies of any documents, records and books pertaining
to this investment and (ii) any such documents, records and books that the Purchaser requested have been made available for inspection
by the Purchaser, the Purchaser’s attorney, accountant or other advisor(s). The Purchaser has requested, received, reviewed
and considered all information it deems relevant in making an informed decision to purchase the Securities. 


 


(3)          The
Purchaser and the Purchaser’s advisor(s) have had a reasonable opportunity to ask questions of and receive answers from representatives
of the Company or Persons (as defined below) acting on behalf of the Company concerning the Company, the Offering and the Securities
and all such questions have been answered to the full satisfaction of the Purchaser. For purposes of this Agreement, “Person”
means an individual, a limited liability company, a partnership, a joint venture, a corporation, a trust, an unincorporated organization,
any other entity and a government or any department or agency thereof.


 


(4)          The
Purchaser is not subscribing for Securities as a result of or subsequent to any advertisement, article, notice or other communication
published in any newspaper, magazine or similar media or broadcast over television, radio or the Internet (including without limitation,
internet “blogs,” bulletin boards, discussion groups and social networking sites) or presented at any seminar, meeting
or conference whose attendees have been invited by any general solicitation or general advertising. 


 


(5)          If
the Purchaser is a natural Person, the Purchaser has reached the age of majority in the state in which the Purchaser resides. The
Purchaser has adequate means of providing for the Purchaser’s current financial needs and contingencies, is able to bear
the substantial economic risks of an investment in the Securities for an indefinite period of time, has no need for liquidity in
such investment and can afford a complete loss of such investment.


 


(6)          The
Purchaser has sufficient knowledge and experience in financial, tax and business matters to enable the Purchaser to utilize the
information made available to the Purchaser in connection with the Offering, to evaluate the merits and risks of an investment
in the Securities and to make an informed investment decision with respect to an investment in the Securities on the terms described
in the Offering Documents. The Purchaser has independently evaluated the merits and risks of its decision to purchase the Securities
pursuant to the Offering Documents, and the Purchaser confirms that it has not relied on the advice of the Company’s or any
other Purchaser’s business and/or legal counsel in making its investment decision. Such Purchaser confirms that none of such
Persons has made any representations or warranties to such Purchaser in connection with the transactions contemplated by the Offering
Documents.


 



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(7)          The
Purchaser will not sell or otherwise transfer the Securities without registration under the Securities Act and applicable state
securities laws or an applicable exemption therefrom. The Purchaser acknowledges that neither the offer nor sale of the Securities
has been registered under the Securities Act or under the securities laws of any state. The Purchaser represents and warrants that
the Purchaser is acquiring the Securities for the Purchaser’s own account, for investment purposes and not with a view toward
resale or distribution within the meaning of the Securities Act, except pursuant to sales registered or exempted under the Securities
Act. The Purchaser is acquiring the Securities in the ordinary course of business. The Purchaser has not offered or sold the Securities
being acquired nor does the Purchaser have any present intention of selling, distributing or otherwise disposing of such Securities
either currently or after the passage of a fixed or determinable period of time or upon the occurrence or non-occurrence of any
predetermined event or circumstances in violation of the Securities Act. The Purchaser is aware that (i) the Securities are not
currently eligible for sale in reliance upon Rule 144 (as defined below) and (ii) the Company has no obligation to register the
Securities purchased hereunder. By making these representations herein, the Purchaser is not making any representation or agreement
to hold the Securities for any minimum or other specific term and reserves the right to dispose of the Securities at any time in
accordance with or pursuant to a registration statement or an available exemption to the registration requirements of the Securities
Act.


 


(8)          The
Purchaser understands that except for the piggy-back registration rights provided in Section E hereof: (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, (B) the Purchaser shall have delivered to the Company an
opinion of counsel, in a form reasonably acceptable to the Company, to the effect that such Securities to be sold, assigned or
transferred may be sold, assigned or transferred pursuant to an exemption from such registration, or (C) the Purchaser provides
the Company with reasonable assurance that such Securities can be sold, assigned or transferred pursuant to Rule 144 or Rule 144A
promulgated under the Securities Act (or a successor rule thereto) (collectively, “Rule 144”); (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 SEC 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. 


 



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(9)          The
Purchaser acknowledges that any certificates or other evidence that may be issued representing the Securities shall bear any legend
required by the securities laws of any state and be stamped or otherwise imprinted with a legend substantially in the following
form: 


 


The securities represented hereby
have not been registered under the Securities Act of 1933, as amended, or any state securities laws and neither the securities
nor any interest therein may be offered, sold, transferred, pledged or otherwise disposed of except pursuant to an effective registration
under such act or an exemption from registration, which, in the opinion of counsel reasonably satisfactory to this corporation,
is available.


 


Certificates
evidencing the Securities shall not be required to contain such legend or any other legend (i) following any sale of such Securities
pursuant to Rule 144, or (ii) if such Securities have been sold pursuant to the Registration Statement (as hereafter defined) and
in compliance with the obligations set forth in Section E(6) below, or (iii) such legend is not required under applicable requirements
of the Securities Act (including judicial interpretations and pronouncements issued by the Staff of the SEC), in each such case
(i) through (iii) to the extent determined by the Company’s legal counsel in its sole discretion. Each Purchaser, severally
and not jointly with the other Purchasers, agrees that the removal of such legend from certificates evidencing the Securities is
predicated upon (i) the reliance by the Company that the Purchaser will sell such Securities pursuant to either the registration
requirements of the Securities Act, including any applicable prospectus delivery requirements, or an exemption therefrom, and/or
(ii) that in the context of a sale under Rule 144, if requested by the transfer agent of the Securities, the Purchaser shall have
signed and delivered a representation letter relating to the Purchaser’s Securities.


 


(10)          If
this Agreement is executed and delivered on behalf of a partnership, corporation, trust, estate or other entity: (i) such partnership,
corporation, trust, estate or other entity is duly organized and validly existing and has the full legal right and power and all
authority and approval required (a) to execute and deliver this Agreement and all other instruments executed and delivered by or
on behalf of such partnership, corporation, trust, estate or other entity in connection with the purchase of its Securities, and
(b) to purchase and hold such Securities; (ii) the signature of the party signing on behalf of such partnership, corporation, trust,
estate or other entity is binding upon such partnership, corporation, trust, estate or other entity; and (iii) such partnership,
corporation, trust or other entity has not been formed for the specific purpose of acquiring such Securities, unless each beneficial
owner of such entity is qualified as an accredited investor within the meaning of Rule 501(a) of Regulation D promulgated under
the Securities Act and has submitted information to the Company substantiating such individual qualification.


 


(11)          If
the Purchaser is a retirement plan or is investing on behalf of a retirement plan, the Purchaser acknowledges that an investment
in the Securities poses additional risks, including the inability to use losses generated by an investment in the Securities to
offset taxable income.


 



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(12)          The
information contained in the purchaser questionnaire in the form of Exhibit C attached hereto (the “Purchaser Questionnaire”)
delivered by the Purchaser in connection with this Agreement is complete and accurate in all respects. The Purchaser is (i) an
“accredited investor” as defined in Rule 501(a) of Regulation D under the Securities Act (“Regulation D”)
on the basis indicated therein, or (ii) is not a U.S. Person as defined in Regulation S under the Securities Act (“Regulation
S”) and is a resident of the jurisdiction set forth therein. The Purchaser is not required to be a registered broker-dealer
under Section 15 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”). The information contained
in the selling stockholder questionnaire in the form of Exhibit D attached hereto (the “Selling Stockholder Questionnaire”)
and the anti-money laundering information form in the form of Exhibit E attached hereto (the “Anti-Money Laundering
Information Form”) delivered by the Purchaser in connection with this Agreement are complete and accurate in all respects.
The Purchaser will notify the Company immediately of any changes in any such information contained in such Purchaser’s Purchaser
Questionnaire, Selling Stockholder Questionnaire, or Anti-Money Laundering Information Form until such time as the Purchaser has
sold all of its shares of Common Stock issuable upon the exercise of the Warrants or, if the shares of Common Stock are registered
pursuant to Section E, until the Company is no longer required to keep the Registration Statement, as defined in Section E below,
effective, except to the extent that such changed information is not required under the Securities Act to be disclosed in an amendment
or supplement to the Registration Statement. 


 


(13)          The
Purchaser acknowledges that the Company will have the authority to issue additional shares of Common Stock and other securities
of the Company in excess of the Securities being issued in connection with the Offering, and that the Company may issue additional
shares of Common Stock and other securities of the Company from time to time, which may cause dilution of the existing shares of
Common Stock and a decrease in the market price of such existing shares of Common Stock.


 


(14)          The
Purchaser acknowledges that the Company has existing contractual commitments to broker-dealers for which the Company may be required
to pay a commission upon the closing of the Offering up to ten percent (10%) of some portion of the aggregate consideration received
by the Company from the Offering and warrants equal to up to six percent (6%) of some portion of the aggregate consideration received
by the Company from the Offering, which warrants, if any, would be exercisable for a period of five years, at an exercise price
equal to $1.00 per share of Common Stock.


 


(15)          The
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 in part upon the truth and accuracy
of, and the Purchaser's compliance with, the representations, warranties, agreements, acknowledgments and understandings of the
Purchaser set forth herein in order to determine the availability of such exemptions and the eligibility of the Purchaser to acquire
the Securities.


 



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(16)          The
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.


 


(17)          This
Agreement has been duly and validly authorized, executed and delivered on behalf of the Purchaser and shall constitute the legal,
valid and binding obligations of such Purchaser enforceable against the Purchaser in accordance its terms.


 


(18)          The
execution, delivery and performance by the Purchaser of this Agreement and the consummation by the Purchaser of the transactions
contemplated hereby will not (i) result in a violation of the organizational documents of the Purchaser or (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 the 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 the 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 the Purchaser to perform its obligations hereunder.


 


(19)          The
Purchaser acknowledges that any estimates or forward-looking statements included in the Company’s Publicly Available Information
were prepared by the Company in good faith but that the attainment of any such estimates or forward-looking statements cannot be
guaranteed by the Company and should not be relied upon.


 


(20)          No
oral or written representations have been made, or oral or written information furnished, to the Purchaser or its advisers, if
any, in connection with the Offering which are in any way inconsistent with the information contained in the Company’s Publicly
Available Information.


 


(21)          Other
than consideration that may be payable by the Company to broker-dealers as disclosed in Section B(14), the Purchaser has not entered
into any agreement or arrangement that would entitle any broker
or finder to compensation by the Company in connection with the sale of the Securities to such Purchaser.


 


(22)          The
Purchaser has, in connection with its purchase of the Securities, complied with all applicable provisions of the Securities Act,
including the rules and regulations promulgated by the SEC thereunder, and applicable state securities laws. 


 


(23)          Each
Purchaser who is not a US Person as defined in Regulation S (“US Person”) represents and warrants as follows:


 


(i)          (a)
the Purchaser is not a US Person and is not acting for the account or benefit of a US Person and (b) the Purchaser is purchasing
the Securities in an offshore transaction pursuant to Regulation S;


 



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(ii)          the
Purchaser understands that the Securities have not been and will not be registered under the Securities Act and may not be offered,
resold, pledged or otherwise transferred by such Purchaser except (a) (i) in the United States to a person whom the seller reasonably
believes is a qualified institutional buyer in a transaction meeting the requirements of Rule 144, (ii) outside the United States
in a transaction complying with the provisions of Rule 903 or Rule 904 of Regulation S, (iii) pursuant to an exemption from registration
under the Securities Act provided by Rule 144 (if available), or (iv) pursuant to an effective registration statement under the
Securities Act, and (b) in accordance with any applicable securities laws of any state of the United States and other jurisdictions;


 


(iii)          the
Purchaser understands and agrees that, if in the future it decides to resell, pledge or otherwise transfer the Securities or any
beneficial interests in any Securities prior to the date which is twelve (12) months after the later of (a) the date when the Securities
are first offered to persons (other than distributors) pursuant to Regulation S and (b) the date of closing of the Offering, it
will do so only (i) in compliance with the restrictions set forth herein, (ii) pursuant to an effective registration statement
under the Securities Act, or (iii) in accordance with the provisions of Rule 144 (if available) or Regulation S, and in each of
such cases in accordance with any applicable securities laws of any state of the United States;


 


(iv)          the
Purchaser agrees to, and each subsequent holder is required to, notify any purchaser of the Securities from it of the resale restrictions
referred to in paragraphs (ii) and (iii) above, if then applicable;


 


(v)          the
Purchaser acknowledges that, prior to any proposed transfer of the Securities other than pursuant to an effective registration
statement, the transferee of the Securities may be required to provide certifications and other documentation relating to the non-US
Person status of such transferee.


 


The
Purchaser should check the Office of Foreign Assets Control (“OFAC”) website at http://www.treas.gov/ofac before
making the representations contained in Sections B(24) and B(25) hereof.


 


(24)          The
Purchaser represents that the amounts invested by it in the Offering were not and are not directly or indirectly derived from activities
that contravene federal, state or international laws and regulations, including anti-money laundering laws and regulations. Federal
regulations and Executive Orders administered by OFAC prohibit, among other things, the engagement in transactions with, and the
provision of services to, certain foreign countries, territories, entities and individuals. The lists of OFAC prohibited countries,
territories, persons and entities can be found on the OFAC website at http://www.treas.gov/ofac. In addition, the programs administered
by OFAC (the “OFAC Programs”) prohibit dealing with individuals1 or entities in certain countries
regardless of whether such individuals or entities appear on the OFAC lists.


 







 


 1
These individuals include specially designated nationals, specially designated narcotics traffickers and other parties
subject to OFAC sanctions and embargo programs.


 



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(25)          To
the best of the Purchaser’s knowledge, none of: (1) the Purchaser; (2) any Person controlling or controlled by the Purchaser;
(3) if the Purchaser is a privately-held entity, any Person having a beneficial interest in the Purchaser; or (4) any Person for
whom the Purchaser is acting as agent or nominee in connection with this investment is a country, territory, individual or entity
named on an OFAC list, or a person or entity prohibited under the OFAC Programs. Please be advised that the Company may not accept
any amounts from a prospective investor if such prospective investor cannot make the representation set forth in the preceding
paragraph. The Purchaser agrees to promptly notify the Company should the Purchaser become aware of any change in the information
set forth in these representations. The Purchaser understands and acknowledges that, by law, the Company may be obligated to “freeze
the account” of the Purchaser, either by prohibiting additional subscriptions from the Purchaser, declining any redemption
requests and/or segregating the assets in the account in compliance with governmental regulations. The Purchaser further acknowledges
that the Company may, by written notice to the Purchaser, suspend the redemption rights, if any, of the Purchaser if the Company
reasonably deems it necessary to do so to comply with anti-money laundering regulations applicable to the Company or any of the
Company’s other service providers. These individuals include specially designated nationals, specially designated narcotics
traffickers and other parties subject to OFAC sanctions and embargo programs.


 


(26)          To
the best of the Purchaser’s knowledge, none of: (1) the Purchaser; (2) any Person controlling or controlled by the Purchaser;
(3) if the Purchaser is a privately-held entity, any Person having a beneficial interest in the Purchaser; or (4) any Person for
whom the Purchaser is acting as agent or nominee in connection with this investment is a senior foreign political figure,2
or any immediate family3 member or close associate4 of a senior foreign political figure, as such terms are
defined in the footnotes below.


 







 





2
A “senior foreign political figure” is defined as a senior official in the executive, legislative, administrative,
military or judicial branches of a foreign government (whether elected or not), a senior official of a major foreign political
party, or a senior executive of a foreign government-owned corporation. In addition, a “senior foreign political figure”
includes any corporation, business or other entity that has been formed by, or for the benefit of, a senior foreign political
figure.


 


3
“Immediate family” of a senior foreign political figure typically includes the figure’s parents,
siblings, spouse, children and in-laws.


 


4 A “close associate” of
a senior foreign political figure is a person who is widely and publicly known to maintain an unusually close relationship with
the senior foreign political figure, and includes a person who is in a position to conduct substantial domestic and international
financial transactions on behalf of the senior foreign political figure.







 



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(27)          If
the Purchaser is affiliated with a non-U.S. banking institution (a “Foreign Bank”), or if the Purchaser receives
deposits from, makes payments on behalf of, or handles other financial transactions related to a Foreign Bank, the Purchaser represents
and warrants to the Company that: (i) the Foreign Bank has a fixed address, other than solely an electronic address, in a country
in which the Foreign Bank is authorized to conduct banking activities; (ii) the Foreign Bank maintains operating records related
to its banking activities; (iii) the Foreign Bank is subject to inspection by the banking authority that licensed the Foreign Bank
to conduct banking activities; and (iv) the Foreign Bank does not provide banking services to any other Foreign Bank that does
not have a physical presence in any country and that is not a regulated affiliate.


 


		C.	Representations and Warranties of the Company 



 


Except
as disclosed in the Company’s Publicly Available Information, the Company hereby makes the following representations and
warranties to the Purchasers. For purposes of this Section C, the phrase “to the knowledge of the Company” or
any phrase of similar import shall be deemed to refer to the actual knowledge Joseph Pandolfino or Henry Sicignano III, as well
as any other knowledge that such individuals would have possessed had they made reasonable inquiry with respect to the matters
in question.


 


(1)          Organization,
Good Standing and Qualification. The Company is a corporation duly organized, validly existing and in good standing under the
laws of the State of Nevada and has full corporate power and authority to conduct its business as currently conducted. The Company
is duly qualified to do business as a foreign corporation and is in good standing in all jurisdictions in which the character of
the property owned or leased or the nature of the business transacted by it makes qualification necessary, except where any failure
to be so qualified would not, individually or in the aggregate, have a Material Adverse Effect on (i) the business, properties,
financial condition or results of operations of the Company or (ii) the transactions contemplated hereby and by the other Offering
Documents or by the agreements and instruments to be entered into in connection herewith or therewith or on the ability of the
Company to perform its obligations under the Offering Documents (a “Material Adverse Effect”). 


 


(2)          Capitalization.
As of the date of this Agreement, 29,049,646 shares of Common Stock of the Company were issued and outstanding and an additional
14,584,018 shares of Common Stock of the Company are issuable upon exercise of convertible debt, warrants and options. All
outstanding warrants of the Company contain a cashless exercise provision. Other than the foregoing securities of the Company,
the warrants that may be issuable as provided in Section B(14) in the event of the Closing of the Offering and as otherwise set
forth above or as contemplated in this Agreement, (a) there are no other options, warrants, calls, rights, commitments or agreements
of any character to which the Company is a party or by which either the Company is bound or obligating the Company to issue, deliver,
sell, repurchase or redeem, or cause to be issued, delivered, sold, repurchased or redeemed, any shares of the capital stock of
the Company or obligating the Company to grant, extend or enter into any such option, warrant, call, right, commitment or agreement
and (b) the issuance and sale of the Securities contemplated hereby will not give rise to any preemptive rights, rights of first
refusal or other similar rights on behalf of any Person. 


 



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(3)          Issuance
of Securities. The Securities and the shares of Common Stock underlying the Securities and their issuance have been duly and
validly authorized by all necessary action and no further action is required by the Company in connection therewith. The Securities
and the shares of Common Stock underlying the Securities, when issued and paid for pursuant to this Agreement, will be validly
issued, fully paid and non-assessable securities of the Company. The issuance of the Securities may result in the right of holders
of other securities of the Company to adjust the exercise, conversion, exchange or reset price under such securities. 


 


(4)          Authorization;
Enforceability. The Company has all corporate right, power and authority to enter into this Agreement and to consummate the
transactions contemplated hereby. All corporate action on the part of the Company necessary for the authorization, execution, delivery
and performance of this Agreement by the Company has been taken and no further action is required by the Company in connection
therewith. This Agreement has been (or upon delivery will have been) duly executed by the Company and, when delivered in accordance
with the terms hereof, will constitute the legal, valid and binding obligation of the Company, enforceable against the Company
in accordance with its terms except as limited by (i) applicable bankruptcy, insolvency, reorganization, moratorium and other laws
of general application affecting enforcement of creditors' rights generally, (ii) laws relating to the availability of specific
performance, injunctive relief or other equitable remedies, and (iii) laws, or public policy underlying such laws, relating to
indemnification and contribution. 


 


(5)          No
Conflict; Governmental and Other Consents.


 


(a)          The
execution and delivery by the Company of this Agreement, the issuance of the Securities by the Company, and the consummation of
the transactions contemplated hereby will not result in the violation (i) assuming the accuracy of the representations and warranties
of each Purchaser, of any law, statute, rule, regulation, order, writ, injunction, judgment or decree of any court or governmental
authority to or by which the Company is bound, or (ii) of any provision of the Certificate of Incorporation or Bylaws of the Company,
and will not conflict with, or result in a breach or violation of, any of the terms or provisions of, or constitute (with due notice
or lapse of time or both) a default under or give to others any rights of termination, amendment, acceleration or cancellation
of, any lease, loan agreement, mortgage, security agreement, trust indenture or other agreement or instrument to which the Company
is a party or by which it is bound or to which any of its properties or assets is subject, nor result in the creation or imposition
of any lien upon any of the properties or assets of the Company, except in each case to the extent that any such violation, conflict
or breach would not be reasonably likely to have a Material Adverse Effect.


 


(b)          Assuming
the accuracy of the representations and warranties of each Purchaser party hereto, no consent, approval, authorization or other
order of any governmental authority or stock exchange, or other third-party is required to be obtained by the Company in connection
with the authorization, execution and delivery of this Agreement or with the authorization, issue and sale of the Securities, except
such post-Closing filings as may be required to be made with the SEC, and with any state or foreign “Blue Sky” or securities
regulatory authority, or as would not be reasonably likely to have a Material Adverse Effect on the Company.


 



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(6)          Litigation.
There are no pending or, to the Company’s knowledge, threatened legal or governmental proceedings against the Company or
any of its subsidiaries or any of their respective officers or directors, which, if adversely determined, would individually or
in the aggregate be reasonably likely to have a Material Adverse Effect on the Company. There is no action, suit, proceeding, inquiry
or investigation before or by any court, public board or body pending or, to the knowledge of the Company, threatened against or
affecting the Company or any of its subsidiaries or any of their respective officers or directors, wherein an unfavorable decision,
ruling or finding could adversely affect the validity or enforceability of, or the authority or ability of the Company to perform
its obligations under this Agreement. Neither the Company nor any Subsidiary (as defined below), nor any director or officer thereof
(in his or her capacity as such), is or has been the subject of any action involving a claim or violation of or liability under
federal or state securities laws or a claim of breach of fiduciary duty.


 


(7)          Financial
Information. The Company’s financial statements that appear in the public filings of the Company as filed with the SEC
have been prepared in accordance with United States generally accepted accounting principles (“GAAP”), except
in the case of unaudited statements or as may be indicated therein or in the notes thereto, applied on a consistent basis throughout
the periods indicated and such financial statements fairly present in all material respects the financial condition and results
of operations and cash flows of the Company as of the dates and for the periods indicated therein (subject, in the case of unaudited
statements, to normal year-end audit adjustments). 


 


(8)          Absence
of Certain Changes. Other than as publically disclosed in the Publically Available Information, since the date of the Company’s
most recent financial statements contained in the public filings of the Company as filed with the SEC, (i) there has not occurred
any event not disclosed in the Company’s Publicly Available Information that individually or in the aggregate has caused
a Material Adverse Effect or any occurrence, circumstance or combination thereof that reasonably would be likely to result in a
Material Adverse Effect, (ii) the Company has not incurred any liabilities (contingent or otherwise) other than (A) trade payables
and accrued expenses incurred in the ordinary course of business, (B) liabilities that would not be required to be reflected in
the Company's financial statements pursuant to GAAP, or (C) obligations pursuant to the agreements with Rodman & Renshaw (iii)
the Company has not (A) declared or paid any dividends, (B) amended or changed the Certificate of Incorporation or Bylaws of the
Company or similar corporate or limited liability company documents of its Subsidiaries, or (C) altered its method of accounting
or the identity of its auditors and (iv) the Company has not made a material change in officer compensation except in the ordinary
course of business consistent with past practice.


 



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(9)          Investment
Company. The Company is not an “investment company” within the meaning of such term under the Investment Company
Act of 1940, as amended, and the rules and regulations of the SEC thereunder.


 


(10)          Subsidiaries.
22nd Century Limited, LLC is a wholly-owned Subsidiary of the Company. Hercules Pharmaceuticals, LLC is a wholly-owned Subsidiary
of 22nd Century Limited, LLC. Goodrich Tobacco Company, LLC is a 96% owned Subsidiary of the Company. For the purposes of this
Agreement, “Subsidiary” shall mean any company or other entity of which at least 50% of the securities or other
ownership interest having ordinary voting power for the election of directors or other Persons performing similar functions are
at the time owned directly or indirectly by the Company or any of its other Subsidiaries. The Company or one of its Subsidiaries
has the unrestricted right to vote, and subject to limitations imposed by applicable law, to receive dividends and distributions
on all capital securities of its Subsidiaries as owned by the Company or such Subsidiary. 


 


(11)          Certain
Fees. Other than compensation that may payable pursuant to Section
B(14) as a result of the Closing of the Offering, no brokers’, finders’ or financial advisory fees or commissions
will be payable by the Company with respect to the transactions contemplated by this Agreement.


 


(12)          No
Violation or Default. Neither the Company nor any of its Subsidiaries is (i) in violation of any law, statute, rule, regulation,
order, writ, injunction, judgment or decree of any court, or (ii) in violation of any provision of its charter or bylaws, or (iii)
in violation of or default under any lease, loan agreement, mortgage, security agreement, trust indenture or other agreement or
instrument to which the Company is a party or by which it is bound or to which any of its properties or assets is subject, except
in each case to the extent that any such violation or default is disclosed in the Company’s Publicly Available Information
or would not be reasonably likely to have a Material Adverse Effect. 


 


(13)          Taxes.
The Company has filed or has valid extensions of the time to file all necessary material federal, state, and foreign income and
franchise tax returns due prior to the date hereof and has paid or accrued all taxes shown as due thereon, and the Company has
no knowledge of any material tax deficiency which has been or might be asserted or threatened against it which could reasonably
be expected to result in a Material Adverse Effect.


 


(14)          Insurance.
The Company is insured by insurers of recognized financial responsibility against such losses and risks and in such amounts as
the Company believes are prudent and customary in the businesses in which the Company is engaged. The Company has no reason to
believe that it will not be able to renew its existing insurance coverage as and when such coverage expires or to obtain similar
coverage from similar insurers as may be necessary to continue its business without an increase in cost significantly greater than
general increases in cost experienced for similar companies in similar industries with respect to similar coverage.


 



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(15)          
Intellectual Property Rights and Licenses. Except as disclosed in the Company’s Publicly Available Information, the
Company owns or possesses adequate rights or licenses to use any and all information, know-how, trade secrets, patents, copyrights,
trademarks, service marks, trade names, domain names, software, formulae, methods, processes and other intangible properties (“Intangible
Rights”) that are of a such nature and significance to its business that the failure to own or have the right to use
or derivatize such items individually or in the aggregate would have a Material Adverse Effect. The Company has not received any
notice that it is in conflict with or infringing upon the asserted intellectual property rights of others, and neither the use
of the Intangible Rights nor the operation of the Company’s businesses is infringing or has infringed upon any intellectual
property rights of others. Except as disclosed in the Company’s Publicly Available Information, all payments have been duly
made that are necessary to maintain the Intangible Rights in force. Except as disclosed in the Company’s Publicly Available
Information, no claims have been made and no claims are threatened, that oppose or challenge the validity, scope or title to any
Intangible Right of the Company. The Company and each of its Subsidiaries have taken reasonable steps to obtain and maintain in
force all licenses and other permissions under Intangible Rights of third parties necessary to conduct their businesses as heretofore
conducted by them, now being conducted by them or are otherwise reasonably anticipated to be conducted, and the Company and each
of its Subsidiaries are not, have not been and do not anticipate being in material breach of any such license or other permission.


 


(16)          Compliance
with Law; Foreign Corrupt Practices. The Company is in compliance with all applicable laws, except for such noncompliance that
individually or in the aggregate would not reasonably be likely to have a Material Adverse Effect. The Company has not received
any notice of, nor does the Company have any knowledge of, any violation (or of any investigation, inspection, audit or other proceeding
by any governmental entity involving allegations of any violation) of any applicable law involving or related to the Company which
has not been dismissed or otherwise disposed of that individually or in the aggregate would be reasonably likely to have a Material
Adverse Effect. The Company has not received notice or otherwise has any knowledge that the Company is charged with, threatened
with or under investigation with respect to, any violation of any applicable law that individually or in the aggregate would reasonably
be likely to have a Material Adverse Effect.


 


(17)          Ownership
of Property. Except as set forth in the Company’s financial statements included in the Company’s Publicly
Available Information, the Company has (i) good and marketable fee simple title to its owned real property,
if any, free and clear of all liens, except for liens which do not individually or in the aggregate have a Material Adverse Effect;
(ii) a valid leasehold interest in all leased real property, and each of such leases is valid and enforceable in accordance with
its terms (subject to laws of general application relating to bankruptcy, insolvency and the relief of debtors and rules of law
governing specific performance, injunctive relief or other equitable remedies, and to limitations of public policy), except as
would not be reasonably likely to have a Material Adverse Effect, and (iii) good title to, or valid leasehold interests in, all
of its other material properties and assets free and clear of all liens, except for liens which do not individually or in the aggregate
have a Material Adverse Effect. 


 



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(18)          No
Integrated Offering. Neither the Company, nor, to its knowledge, any of its affiliates or other Person acting on the Company’s
behalf has, directly or indirectly, made any offers or sales of any security or solicited any offers to buy any security under
circumstances that would cause the Offering of the Securities to be integrated with prior offerings by the Company for purposes
of the Securities Act, when integration would cause the Offering not to be exempt from the registration requirements of Section
5 of the Securities Act. 


 


(19)          No
General Solicitation. Neither the Company nor, to its knowledge, any Person acting on behalf of the Company, has offered or
sold any of the Securities by any form of “general solicitation” within the meaning of Rule 502 under the Securities
Act. To the knowledge of the Company, no Person acting on its behalf has offered the Securities for sale other than to the Purchasers
and certain other “accredited investors” within the meaning of Rule 501 under the Securities Act.


 


(20)          No
Registration. Assuming the accuracy of the representations and warranties made by, and compliance with the covenants of, the
Purchasers in Section B hereof, and other than as required under this Agreement, no registration of the Securities under the Securities
Act is required in connection with the offer and sale of the Securities by the Company to the Purchasers.


 


(21)         Transfer
Taxes. On the Closing Date, all stock transfer or other taxes (other than income or similar taxes) which are required to be
paid in connection with the sale and transfer of the Securities to be sold to each Purchaser hereunder will be, or will have been,
fully paid or provided for by the Company, and all laws imposing such taxes will be or will have been complied with.


 


(22)          Environmental
Matters. The Company has obtained, or has applied for, and is in compliance with and in good standing under all permits required
under Environmental Laws (except for such failures that individually or in the aggregate would not be reasonably likely to have
a Material Adverse Effect) and the Company has no knowledge of any proceedings to substantially modify or to revoke any such permit.
There are no investigations, proceedings or litigation pending or, to the Company's knowledge, threatened against the Company or
any of the Company’s facilities relating to Environmental Laws or hazardous substances that individually or in the aggregate
would not be reasonably likely to have a Material Adverse Effect. “Environmental Laws” shall mean all federal,
national, state, regional and local laws, statutes, ordinances and regulations, in each case as amended or supplemented from time
to time, and any judicial or administrative interpretation thereof, including orders, consent decrees or judgments relating to
the regulation and protection of human health, safety, the environment and natural resources. 


 


(23)          Publicly
Available Information. The documents constituting the Company’s Publicly Available Information, when they were filed
with the SEC, conformed in all material respects to the requirements of the Securities Act or Exchange Act, as applicable. 


 



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(24)          Acknowledgment
Regarding Purchaser's Purchase of Securities. The Company acknowledges and agrees that except as set forth on the signature
page of this Agreement, no Purchaser is (i) an officer or director of the Company, (ii) an “affiliate” of the Company
(as defined in Rule 144) or (iii) to the knowledge of the Company, a “beneficial owner” of more than 10% of the shares
of Common Stock (as defined for purposes of Rule 13d-3 of the Exchange Act). The Company further acknowledges that no Purchaser
is acting as a financial advisor or fiduciary of the Company (or in any similar capacity) with respect to the Offering Documents
and the transactions contemplated hereby and thereby.


 


(25)          Employee
Relations. The Company is not a party to any collective bargaining agreement and, to its knowledge, its employees are not union
members. Each of the Company and its Subsidiaries is in compliance with all federal, state, local and foreign laws and regulations
respecting labor, employment and employment practices and benefits, terms and conditions of employment and wages and hours, except
where failure to be in compliance would not, either individually or in the aggregate, reasonably be expected to result in a Material
Adverse Effect. No material labor dispute exists or, to the knowledge of the Company, is imminent with respect to any employees
of the Company.


 


(26)          Use
of Proceeds. The Company intends to use the proceeds from the Offering for working capital and other general corporate purposes.


 


		D.	Understandings



 


Each of the Purchasers
understands, acknowledges and agrees with the Company as follows:


 


(1)          No
federal, state or foreign agency or authority has made any finding or determination as to the accuracy or adequacy of the Offering
Documents or as to the fairness of the terms of the Offering nor any recommendation or endorsement of the Securities. Any representation
to the contrary is a criminal offense. In making an investment decision, the Purchasers must rely on their own examination of the
Company and the terms of the Offering, including the merits and risks involved.


 


(2)          The
Offering is intended to be exempt from registration under the Securities Act by virtue of Sections 4(2) and 4(6) of the Securities
Act and the provisions of Rule 506 of Regulation D and the provisions of Regulation S thereunder, which is in part dependent upon
the truth, completeness and accuracy of the statements made by the Purchaser herein and in the Purchaser Questionnaire.


 


(3)          Notwithstanding
the piggy-back registration rights provided herein, there can be no assurance that the Purchaser will be able to sell or dispose
of the Securities. It is understood that in order not to jeopardize the Offering’s exempt status under Section 4(2) of the
Securities Act, Regulation D and Regulation S, any transferee may, at a minimum, be required to fulfill the investor suitability
requirements thereunder.


 



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(4)          The
Securities purchased hereunder by any Purchaser who is not a US Person under Regulation S are subject to the conditions listed
under Section 903(b)(3), or Category 3, of Regulation S. Under Category 3, Offering Restrictions (as defined under Regulation S)
must be in place in connection with the offering and additional restrictions are imposed on resales of the Securities as described
below. Prior to six months after the later of (1) the time when the Securities are first offered to persons other than distributors
in reliance upon Regulation S or (2) the date of closing of the Offering (the "Compliance Period"), each Purchaser
who is not a US Person:


 


(a)          certifies
that it is not a US Person and is not acquiring the securities for the account or benefit of any US Person or is a US Person who
purchased securities in a transaction that did not require registration under the Securities Act;


 


(b)          agrees
to resell such Securities only in accordance with the provisions of Rule 144 (if available) or Regulation S, or pursuant to registration
under the Securities Act, and agrees to not engage in hedging transactions with regard to the Securities, directly or indirectly,
unless in compliance with the Securities Act;


 


(c)          acknowledges
that the Purchaser has been notified that it is subject to the same restrictions on offers and sales that apply to a distributor;


 


(d)          agrees
that the Company will be required to refuse to register any transfer of the Securities not made in accordance with the provisions
of Rule 144 (if available) or Regulation S, or pursuant to registration under the Securities Act; and


 


(e)          any
certificates evidencing the Securities will contain a legend to the effect that transfer is prohibited except in accordance with
the restrictions set forth in (b) above during the Compliance Period.


 


		E.	Piggy-Back Registration Rights



 


(1)          The
shares of Common Stock purchased pursuant to this Agreement and the shares of Common Stock issuable upon the exercise of the Warrants
will have piggy-back registration rights, which means that in the event the Company files a registration statement under the Securities
Act after the Closing Date of this Offering to register the resale of additional shares of Common Stock issued by or issuable by
the Company pursuant to other securities subsequently sold by the Company in a future securities offering after the Closing Date
of this Offering in an amount of at least Five Million Dollars ($5,000,000) (such future securities offering shall not include
any securities issued by the Company under its equity incentive plans), then such shares of Common Stock will be included in such
registration statement to the extent permitted by the SEC and any applicable underwriter. Notwithstanding the foregoing, the Purchasers
shall not have piggy-back registration rights if such shares of Common Stock are eligible for unlimited resale pursuant to Rule
144.


 



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(2)          Registration
Expenses. If applicable pursuant to Section E(1), the Company shall pay all fees and expenses incident to the performance of
or compliance with this Agreement by the Company, including without limitation (a) all registration and filing fees and expenses,
including without limitation those related to filings with the SEC, in connection with applicable state securities or “Blue
Sky” laws, and to the OTC Bulletin Board (the “OTCBB”), (b) printing expenses (it being understood that
the Company, at its option, may provide the Purchaser with electronic copies of any prospectus or supplement), (c) fees and disbursements
of counsel for the Company and (d) fees and expenses of all other Persons retained by the Company in connection with the consummation
of the transactions contemplated by this Agreement. Notwithstanding the foregoing, each Purchaser shall pay any and all costs,
fees, discounts or commissions attributable to the sale of its respective shares of Common Stock received upon the exercise of
the Warrants and all fees and expenses of its counsel and other advisors.


 


(3)          Indemnification.


 


(a)          Indemnification
by the Company. The Company agrees to indemnify and hold harmless each Purchaser, the partners, members, officers and directors
of each Purchaser and each Person or entity, if any, who controls such Purchaser or any of the foregoing within the meaning of
Section 15 of the Securities Act or Section 20 of the Exchange Act, from and against any losses, claims, damages or liabilities
(collectively, “Losses”) to which they may become subject (under the Securities Act or otherwise) insofar as
such Losses (or actions or proceedings in respect thereof) arise out of, or are based upon, any material breach of this Agreement
or any other Offering Document by the Company or any untrue statement or alleged untrue statement of a material fact contained
in a registration statement or any omission or alleged omission to state therein a material fact required to be stated therein
or necessary to make the statements therein, in light of the circumstances under which they were made, not misleading or arise
out of any failure by the Company to fulfill any undertaking included in a registration statement and the Company will, as incurred,
reimburse such Purchaser, partner, member, officer, director or controlling Person for any legal or other expenses reasonably incurred
in investigating, defending or preparing to defend any such action, proceeding or claim; provided, however, that the Company shall
not be liable in any such case to the extent that such Loss arises out of, or is based upon, an untrue statement or omission or
alleged untrue statement or omission made in such registration statement in reliance upon and in conformity with written information
furnished to the Company by or on behalf of such Purchaser, partner, member, officer, director or controlling Person specifically
for use in preparation of a registration statement or any breach of this Agreement by such Purchaser; provided further, however,
that the Company shall not be liable to any Purchaser of registrable Securities (or any partner, member, officer, director or controlling
Person of such Purchaser) to the extent that any such Loss is caused by an untrue statement or omission or alleged untrue statement
or omission made in any preliminary prospectus if either (i) (A) such Purchaser failed to send or deliver a copy of the final prospectus
with or prior to, or, if Rule 172 is then in effect, such Purchaser failed to confirm that a final prospectus was deemed to be
delivered prior to, the delivery of written confirmation of the sale by such Purchaser to the Person asserting the claim from which
such Loss resulted and (B) the final prospectus corrected such untrue statement or omission, (ii) (X) such untrue statement or
omission is corrected in an amendment or supplement to the prospectus and (Y) having previously been furnished by or on behalf
of the Company with copies of the prospectus as so amended or supplemented or, if Rule 172 is then in effect, notified by the company
that such amended or supplemented prospectus has been filed with the SEC, such Purchaser thereafter fails to deliver such prospectus
as so amended or supplemented, with or prior to, or, if Rule 172 is then in effect, such Purchaser fails to confirm that the prospectus
as so amended or supplemented was deemed to be delivered prior to, the delivery of written confirmation of the sale of a registrable
Security to the Person asserting the claim from which such Loss resulted or (iii) such Purchaser sold registrable Securities in
violation of such Purchaser’s covenant contained in Paragraph (6) below.


 



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(b)          Indemnification
by Purchasers. Each Purchaser, severally and not jointly, agrees to indemnify and hold harmless the Company (and each Person,
if any, who controls the Company within the meaning of Section 15 of the Securities Act or Section 20 of the Exchange Act, each
officer of the Company who signs the registration statement and each director of the Company), from and against any losses, claims,
damages or liabilities to which the Company (or any such officer, director or controlling Person) may become subject (under the
Securities Act or otherwise), insofar as such losses, claims, damages or liabilities (or actions or proceedings in respect thereof)
arise out of, or are based upon, any material breach of this Agreement by such Purchaser or any untrue statement or alleged untrue
statement of a material fact contained in the registration statement or any omission or alleged omission to state therein a material
fact required to be stated therein or necessary to make the statements therein, in light of the circumstances under which they
were made, not misleading in each case, on the Effective Date thereof, if, and to the extent, such untrue statement or omission
or alleged untrue statement or omission was made in reliance upon and in conformity with written information furnished by or on
behalf of such Purchaser specifically for use in preparation of the registration statement, including, without limitation the Purchaser
Questionnaire, the Selling Stockholder Questionnaire, and the Anti-Money Laundering Information Form, and such Purchaser will reimburse
the Company (and each of its officers, directors or controlling Persons) for any legal or other expenses reasonably incurred in
investigating, defending or preparing to defend any such action, proceeding or claim; provided, however, that in no event shall
any indemnity under this Paragraph be greater in amount than the dollar amount of the proceeds (net of (i) the purchase price of
the registrable Securities included in the registration statement giving rise to such indemnification obligation and (ii) the amount
of any damages such Purchaser has otherwise been required to pay by reason of such untrue statement or omission or alleged untrue
statement or omission) received by such Purchaser upon the sale of such registrable Securities.


 



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(c)          Conduct
of Indemnification Proceedings. If any Proceeding shall be brought or asserted against any Person entitled to indemnity hereunder
(an “Indemnified Party”), such Indemnified Party shall promptly notify the Person from whom indemnity is sought
(the “Indemnifying Party”) in writing, and the Indemnifying Party shall be entitled to participate therein,
and to the extent that it shall wish, assume the defense thereof, including the employment of counsel reasonably satisfactory to
the Indemnified Party and the payment of all fees and expenses incurred in connection with defense thereof. After notice from the
Indemnifying Party to such Indemnified Party of its election to assume the defense thereof, such Indemnifying Party shall not be
liable to such Indemnified Party for any legal expenses subsequently incurred by Indemnified Party in connection with the defense
thereof. An Indemnified Party shall have the right to employ separate counsel in any such Proceeding and to participate in the
defense thereof, but the fees and expenses of such counsel shall be at the expense of such Indemnified Party or Parties. If there
exists or shall exist a conflict of interest that would make it inappropriate in the reasonable judgment of the Indemnified Party
for the same counsel to represent both the Indemnified Party and such Indemnifying Party or any affiliate or associate thereof,
the Indemnified Party shall be entitled to retain its own counsel at the expense of such Indemnifying Party; provided, further,
that no Indemnifying Party be responsible for the fees and expense of more than one separate counsel for all Indemnified Parties.
The Indemnifying Party shall not settle an action without the consent of the Indemnified Party, which consent shall not be unreasonably
withheld, unless such settlement includes an unconditional release of such Indemnified Party from all liability on claims that
are the subject matter of such Proceeding. All reasonable fees and expenses of the Indemnified Party (including reasonable fees
and expenses to the extent incurred in connection with investigating or preparing to defend such Proceeding in a manner not inconsistent
with this Section) shall be paid to the Indemnified Party, as incurred, within ten business days of written notice thereof to the
Indemnifying Party (regardless of whether it is ultimately determined that an Indemnified Party is not entitled to indemnification
hereunder; provided, that the Indemnifying Party may require such Indemnified Party to undertake to reimburse all such fees and
expenses to the extent it is finally judicially determined that such Indemnified Party is not entitled to indemnification hereunder).


 


(d)          Contribution.
If a claim for indemnification under Paragraph (5)(a) or (b) is unavailable to an Indemnified Party (by reason of public policy
or otherwise), then each Indemnifying Party, in lieu of indemnifying such Indemnified Party, shall contribute to the amount paid
or payable by such Indemnified Party as a result of such Losses, in such proportion as is appropriate to reflect the relative fault
of the Indemnifying Party and Indemnified Party in connection with the actions, statements or omissions that resulted in such Losses
as well as any other relevant equitable considerations. The relative fault of such Indemnifying Party and Indemnified Party shall
be determined by reference to, among other things, whether any action in question, including any untrue or alleged untrue statement
of a material fact or omission or alleged omission of a material fact, has been taken or made by, or related to information supplied
by, such Indemnifying Party or Indemnified Party, and the parties’ relative intent, knowledge, access to information and
opportunity to correct or prevent such action, statement or omission. The amount paid or payable by a party as a result of any
Losses shall be deemed to include, subject to the limitations set forth in Paragraph (5)(c), any reasonable attorneys’ or
other reasonable fees or expenses incurred by such party in connection with any Proceeding to the extent such party would have
been indemnified for such fees or expenses if the indemnification provided for in this Paragraph 5(d) was available to such party
in accordance with its terms.


 



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The
parties hereto agree that it would not be just and equitable if contribution pursuant to this Paragraph (5)(d) were determined
by pro rata allocation or by any other method of allocation that does not take into account the equitable considerations referred
to in the immediately preceding paragraph. Notwithstanding the provision of this Paragraph (5)(d), no Purchaser shall be required
to contribute, in the aggregate, any amount in excess of the amount by which the net proceeds actually received by such Purchaser
from the sale of the registrable Securities subject to the Proceeding exceeds the amount of any damages that such Purchaser has
otherwise been required to pay by reason of such untrue or alleged untrue statement or omission or alleged omission. No Person
guilty of fraudulent misrepresentation (within the meaning of Section 11(f) of the Securities Act) shall be entitled to contribution
from any Person who was not guilty of such fraudulent misrepresentation.


 


(4)          Dispositions.     Each Purchaser agrees that it will comply with the prospectus delivery requirements of the Securities Act as applicable to it in
connection with sales of registrable Securities pursuant to the registration statement. Each Purchaser further agrees that, upon
receipt of a notice from the Company of the occurrence of any event of the kind described herein, such Purchaser will discontinue
disposition of such registrable Securities under the registration statement until such Purchaser’s receipt of the copies
of the supplemented prospectus and/or amended registration statement, or until it is advised in writing (the “Advice”)
by the Company that the use of the applicable prospectus may be resumed, and, in either case, has received copies of any additional
or supplemental filings that are incorporated or deemed to be incorporated by reference in such prospectus or registration statement.
The Company may provide appropriate stop orders to enforce the provisions of this paragraph.


 


(5)          Rule
144. Until such time as the registrable Securities are eligible for unlimited resale pursuant to Rule 144 under the Securities
Act, the Company agrees with each holder of registrable Securities to:


 


(a)          comply
with the requirements of Rule 144(c) under the Securities Act with respect to current public information about the Company; and


 


(b)          to
file with the SEC all reports and other documents required of the Company under the Securities Act and the Exchange Act (at any
time it is subject to such reporting requirements).


 



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		F.	Covenants of the Company



 


The
Company agrees to file one or more Forms D with respect to the Securities on a timely basis as required under Regulation D under
the Securities Act to claim the exemption provided by Rule 506 of Regulation D. The Company, on or before the Closing Date, shall
take such action as the Company shall reasonably determine is necessary in order to obtain an exemption for or to qualify the Securities
for sale to the Purchasers at the Closing pursuant to this Agreement under applicable securities or “Blue Sky” laws
of the states of the United States (or to obtain an exemption from such qualification), and shall provide evidence of any such
action so taken to the Purchasers on or prior to the Closing Date. The Company shall make all filings and reports relating to the
offer and sale of the Securities required under applicable securities or “Blue Sky” laws of the states of the United
States following the Closing Date.


 


		G.	Further Covenants of the Company



 


(1)          The
Company shall make a public announcement of the Closing of the Offering by filing with the SEC a Current Report on Form 8-K and
issuing a press release within the time periods required under the federal securities laws.


 


(2)          The
Company shall not publicly disclose the name of any Purchaser, or include the name of any Purchaser in any filing or press release
without the prior written consent of such Purchaser, unless otherwise required by law. The Purchaser consents to the disclosure
of its name and details of its purchase in a subsequent registration statement. The Company shall not, and shall cause each of
its officers, directors, employees and agents to not, knowingly provide any Purchaser with any material nonpublic information regarding
the Company from and after the issuance of the above referenced filings and press release without the express written consent of
such Purchaser. 


 


(3)          The
Company shall use its commercially reasonable efforts to maintain the listing eligibility of the Company Common Stock for quotation
on the OTCBB unless it lists its shares for trading on an alternative stock exchange including at least one in the United States.


 


		H.	Conditions to Closing; Termination



 


(1)          Conditions
Precedent to the Obligations of the Purchasers to Purchase Securities. The obligation of each Purchaser to acquire Securities
at the Closing is subject to the satisfaction or waiver by such Purchaser, at or before the Closing, of each of the following conditions:


 


(a)          The
representations and warranties of the Company contained herein shall be true and correct in all material respects (other than those
representations and warranties that are qualified by “materiality” or Material Adverse Effect qualifiers shall be true
and correct in all respects) as of the date when made and as of the Closing as though made on and as of such date (except to the
extent that such representation or warranty speaks of an earlier date, in which case such representation and warranty shall be
true and correct in all material respects as of the Closing Date with respect to such date);


 



    	22



    	 



    

 


(b)          The
Company shall have performed, satisfied and complied in all material respects with all covenants, agreements and conditions required
by the Offering Documents to be performed, satisfied or complied with by it at or prior to the Closing;


 


(c)          No
statute, rule, regulation, executive order, decree, ruling or injunction shall have been enacted, entered, promulgated or endorsed
by any court or governmental authority of competent jurisdiction that prohibits the consummation of any of the transactions contemplated
by the Offering Documents;


 


(d)          Since
the date of execution of this Agreement, no event or series of events shall have occurred that reasonably could have or result
in a Material Adverse Effect;


 


(e)          Trading
in the Common Stock shall not have been suspended by the SEC or the OTCBB (except for any suspensions of trading of limited duration
agreed to by the Company) at any time since the date of execution of this Agreement, and the Common Stock shall have been at all
times since such date eligible for quotation on the OTCBB;


 


(f)          The
Company shall have delivered the items required to be delivered by the Company in accordance with Section A(4); and


 


(g)          This
Agreement shall not have been terminated as to such Purchaser in accordance with Section H(3).


 


(2)          Conditions
Precedent to the Obligations of the Company to sell Securities. The obligation of the Company to sell Securities at the Closing
is subject to the satisfaction or waiver by the Company, at or before the Closing, of each of the following conditions:


 


(a)          The
representations and warranties of each Purchaser contained herein shall be true and correct in all material respects (other than
those representations and warranties that are qualified by “materiality” or Material Adverse Effect qualifiers, which
shall be true and correct in all respects) as of the date when made and as of the Closing Date as though made on and as of such
date;


 


(b)          Each
Purchaser shall have performed, satisfied and complied in all material respects with all covenants, agreements and conditions required
by the Offering Documents to be performed, satisfied or complied with by such Purchaser at or prior to the Closing;


 



    	23



    	 



    

 


(c)          No
statute, rule, regulation, executive order, decree, ruling or injunction shall have been enacted, entered, promulgated or endorsed
by any court or governmental authority of competent jurisdiction that prohibits the consummation of any of the transactions contemplated
by the Offering Documents;


 


(d)          Each
Purchaser shall have delivered its Investment Amount in accordance with Section A(2); and


 


(e)          This
Agreement shall not have been terminated as to such Purchaser in accordance with Section H(3).


 


(3)          Termination.
This Agreement may be terminated prior to Closing:


 


(a)          By
written agreement of the Purchasers and the Company; and


 


(b)          By
the Company or a Purchaser (as to itself but no other Purchaser) upon written notice to the other, if the Closing shall not have
taken place by 6:30 p.m. Eastern time on or before April 30, 2012 (with the Company reserving the right to further extend
the termination date of the Offering to May 15, 2012 without further notice); provided, that the right
to terminate this Agreement under this Section H(3) shall not be available to any Person whose failure to comply with its obligations
under this Agreement has been the cause of or resulted in the failure of the Closing to occur on or before such time.


 


In
the event of a termination pursuant to Section H(3)(a), the Company shall promptly notify all non-terminating Purchasers. Upon
a termination in accordance with this Section H(3), the Company and the terminating Purchaser(s) shall not have any further obligation
or liability (including as arising from such termination) to the other and no Purchaser will have any liability to any other Purchaser
under the Offering Documents as a result thereof.


 


		I.	Miscellaneous



 


(1)          All
pronouns and any variations thereof used herein shall be deemed to refer to the masculine, feminine, singular or plural, as identity
of the Person or Persons may require. 


 


(2)          Any
notice or other communication required or permitted to be given or delivered under this Agreement shall be in writing and shall
be deemed given and effective on the earliest of (a) the date of transmission, if such notice or communication is delivered by
fax prior to 6:30 p.m. Eastern Time on a business day, (b) the next business day after the date of transmission, if such notice
or communication is delivered by fax on a day that is not a business day or later than 6:30 p.m. Eastern Time on a business day,
(c) upon receipt, if sent by an internationally recognized overnight delivery service (with charges prepaid), or (d) upon actual
receipt by the party to whom such notice or other communication is required to be given:


 



    	24



    	 



    

 


(a)          if
to the Company, to it at: 


22nd Century
Group, Inc.


9530 Main
Street


Clarence,
NY 14031


Fax No.:
(716) 877-3064


Attention:
Joseph Pandolfino


 


or such
other address as it shall have specified to the Purchaser in writing, with a copy (which shall not constitute notice) to:


 


Foley
& Lardner LLP


3000 K
Street N.W., Suite 600


Washington,
D.C. 20007


Fax No.:
(202) 672-5399


Attention:
Thomas L. James, Esq.


 


(b)if
to a Purchaser, to it at its address set forth on the signature page to this Agreement, or such other address as it shall have
specified to the Company in writing.


 


(3)          This
Agreement shall not confer any rights or remedies upon any person other than the parties hereto and their respective successors
and permitted assigns.


 


(4)          Failure
of the Company to exercise any right or remedy under this Agreement or any other agreement among the Company and the Purchaser,
or otherwise, or delay by the Company in exercising such right or remedy, will not operate as a waiver thereof. No waiver by the
Company will be effective unless and until it is in writing and signed by the Company.


 


(5)          This
Agreement shall be enforced, governed and construed in all respects in accordance with the laws of the State of New York, as such
laws are applied by the New York courts to agreements entered into and to be performed in New York by and between residents of
New York, and shall be binding upon the Purchaser, the Purchaser’s heirs, estate, legal representatives, successors and assigns
and shall inure to the benefit of the Company, its successors and assigns. The Company and each Purchaser hereby agree to submit
to the jurisdiction of the courts of the State of New York located within County of Erie with respect to any proceeding arising
out of or relating to this Agreement, and hereby irrevocably waives, and agrees not to assert in any suit, action or proceeding,
any claim that it is not personally subject to the jurisdiction of any such court, that such suit, action or proceeding is brought
in an inconvenient forum or that the venue of such suit, action or proceeding is improper. Each party hereby irrevocably waives
personal service of process and consents to process being served in any such suit, action or proceeding by mailing a copy thereof
to such party at the address for such notices to it under this Agreement and agrees that such service shall constitute good and
sufficient service of process and notice thereof. Nothing contained herein shall be deemed to limit in any way any right to serve
process in any manner permitted by law. EACH PARTY HEREBY IRREVOCABLY WAIVES ANY RIGHT IT MAY HAVE, AND AGREES NOT TO REQUEST,
A JURY TRIAL FOR THE ADJUDICATION OF ANY DISPUTE HEREUNDER OR IN CONNECTION WITH OR ARISING OUT OF THIS AGREEMENT OR ANY TRANSACTION
CONTEMPLATED HEREBY.


 



    	25



    	 



    

 


(6)          If
any provision of this Agreement is held to be invalid or unenforceable under any applicable statute or rule of law, then such provision
shall be deemed modified to conform with such statute or rule of law. Any provision hereof that may prove invalid or unenforceable
under any law shall not affect the validity or enforceability of any other provisions hereof.


 


(7)          The
parties understand and agree that, unless provided otherwise herein, money damages would not be a sufficient remedy for any breach
of the Agreement by the Company or the Purchaser and that the party against which such breach is committed shall be entitled to
equitable relief, including injunction and specific performance, as a remedy for any such breach. Such remedies shall not, unless
provided otherwise herein, be deemed to be the exclusive remedies for a breach by either party of the Agreement but shall be in
addition to all other remedies available at law or equity to the party against which such breach is committed.


 


(8)          The
obligations of each Purchaser under this Agreement are several and not joint with the obligations of any other Purchaser, and no
Purchaser shall be responsible in any way for the performance of the obligations of any other Purchaser hereunder, except as may
result from the actions of any such Purchaser other than through the execution hereof. Nothing contained herein solely by virtue
of being contained herein shall be deemed to constitute the Purchasers as a partnership, an association, a joint venture or any
similar entity, or create a presumption that the Purchasers are in any way acting in concert or as a group with respect to such
obligations or the transactions contemplated hereby.


 


(9)          This
Agreement, together with the agreements and documents executed and delivered in connection with this Agreement, constitutes the
entire agreement between the parties hereto with respect to the subject matter hereof.


 


(10)        This
Agreement may be executed in two or more identical counterparts, all of which shall be considered one and the same agreement and
shall become effective when counterparts have been signed by each party and delivered to the other party; provided that a facsimile
signature shall be considered due execution and shall be binding upon the signatory thereto with the same force and effect as if
the signature were an original, not a facsimile signature.


 


(11)        The
headings of this Agreement are for convenience of reference and shall not form part of, or affect the interpretation of, this Agreement.


 



    	26



    	 



    

 


(12)        This
Agreement and the other Offering Documents (including any schedules and exhibits hereto and thereto) supersede all other prior
oral or written agreements between the Purchaser, the Company, their affiliates and Persons acting on their behalf with respect
to the matters discussed herein, and this Agreement and other Offering Documents (including any schedules and exhibits hereto and
thereto) and the instruments referenced herein contain the entire understanding of the parties with respect to the matters covered
herein and therein and, except as specifically set forth herein or therein, neither the Company nor any Purchaser makes any representation,
warranty, covenant or undertaking with respect to such matters. 


 


(13)        No
provision of this Agreement may be amended other than by an instrument in writing signed by the Company and the Purchasers holding
or being obligated to purchase at least a majority of the Securities. No consideration shall be offered or paid to any Purchaser
to amend or consent to a waiver or modification of any provision of any Offering Document unless the same consideration is also
offered to all Purchasers who then hold the Securities. No provision hereof may be waived other than by an instrument in writing
signed by the party against whom enforcement is sought. 


 


(14)        No
Purchaser may assign any of its rights under this Agreement. 


 


(15)        The
representations and warranties of the parties contained herein or in any other agreements or documents executed in connection herewith
shall survive the Closing. 


 


(16)        Each
party shall do and perform, or cause to be done and performed, all such further acts and things, and shall execute and deliver
all such other agreements, certificates, instruments and documents, as any other party may reasonably request in order to carry
out the intent and accomplish the purposes of this Agreement and the consummation of the transactions contemplated hereby.


 


[Signature Pages to Follow]


 



    	27



    	 



    

 


SIGNATURE
PAGE


 


The Purchaser hereby
agrees to purchase the amount of Common Stock and Warrants in exchange for the Investment Amount, as set forth below, and agrees
to be bound by the terms and conditions of this Agreement.


 


PURCHASER


 


1.        Investment Amount: $___________


 


2.        Number of Shares of Common Stock
Purchased: __________ (this amount equals the Investment Amount divided by $0.60)


 


3.        Number of Warrants Purchased: ________
(this amount equals the Number of Shares)


 





	 	 	 
	Signature of Purchaser	 	Signature of Joint Purchaser
	(and title, if applicable)	 	(if any)
	 	 	 
	 	 	 
	Taxpayer Identification or Social	 	Taxpayer Identification or Social
	Security Number	 	Security Number of Joint Purchaser (if any)
	 	 	 
	 	 	 
	Name (please print as name will appear on Common Stock)	 	 
	 	 	 
	 	 	 
	Number and Street	 	 
	 	 	 
	 	 	 
	City, State	Zip Code	 	 







  


ACCEPTED BY:


 


22ND
cENTURY group, inc.


 


	By:	 
	 	Name:  Henry Sicignano III
	 	Title: President


 



    	 



    	 



    

 


Exhibit A


 


Term Sheet


 





TERM SHEET


 


Summary of Terms and Conditions


of


Private Offering of Common Stock


 


	Note: The terms and conditions presented below do not constitute any form of binding contract but rather are solely for the purpose of outlining those terms pursuant to which a definitive agreement may ultimately be entered into. This Term Sheet does not purport to summarize all the terms, conditions, covenants, representations, warranties and other provisions which would be contained in the definitive legal documentation for the financing contemplated herein. The investment of the Investor is contingent upon completion of due diligence and final negotiation and execution of satisfactory documentation containing customary closing conditions, representations, warranties, etc.


 


		Issuer:	22nd Century Group, Inc. (OTCBB: XXI I) (the “Company”).



 


		Investor(s):	Certain “accredited investors” as selected by the Company (collectively, the “Investors”).



 


		Agent:	____________________________ (“Agent”).



 


		Investment:	$0.60 per share of common stock. The Investors
will purchase up to 2,500,000 shares of Common Stock of the Company for an aggregate purchase price of up to One Million Five
Hundred Thousand Dollars ($1,500,000), which equals a purchase price of $0.60 per share. The Company reserves the right to offer
and sell up to an additional 1,000,000 shares of Common Stock of the Company for an aggregate purchase price of an additional
Six Hundred Thousand Dollars ($600,000), which equals the same purchase price of $0.60 per share (the “Over-Allotment Option”).



 


		Purpose:	Working capital of the Company.



 


		Warrants:	100% warrant coverage, 5-year term, $1.00 strike price, cashless exercise. The Company will also grant warrants
(the “Warrants”) to the Investors to purchase up to 2,500,000 shares of Common Stock of the Company at an exercise
price of $1.00 per share. The right to exercise the Warrants will expire five (5) years from the closing date of the Investment
and the Warrants will contain a cashless exercise provision. In the event the Over-Allotment Option is exercised by the Company,
then the Company will issue Warrants to the Investors to purchase up to an additional 1,000,000 shares of Common Stock.



 


		Registration:	The shares of Common Stock issuable to the Investors as part of the Investment and upon the exercise of the Warrants will have
piggyback registration rights, at the Company’s expense, less discounts and commissions.



 


		Dilution:	After adjusting for stock splits and other changes, if any, to the Company’s capital structure, then in the event the
Company issues warrants in the future with an exercise price of less than $1.00 per share, then the exercise price of the Warrants
issued to the Investors in this transaction will be adjusted to such lower exercise price.



 



    	 



    	 



    

 


		Documentation:	The terms and conditions summarized herein represent the principal terms and conditions which would be incorporated into appropriate
documentation, which will include a securities purchase agreement and related agreements and documents pursuant to which the Common
Stock and Warrants will be purchased (collectively, the “Documentation”), but such terms and conditions summarized
herein are not intended to be an exhaustive description of the Documentation.



 


Transaction

Fees and




		Expenses:	Each party will pay for its own respective fees, commissions, costs, charges, taxes and other expenses incurred in the negotiation
and closing on the Documentation, included but not limited to, fees of the Investor(s)’ counsel and all recording fees, taxes
and charges. The Company will pay for any fees and expenses of the Agent upon the closing of the transactions contemplated herein.



 


		Expiration:	The parties are willing to move forward in this transaction if this Term Sheet is signed by all parties no later than May 15,
2012 and as long as the closing occurs on or before May 15, 2012.



 


SEEN AND AGREED:


 


22nd Century Group, Inc.


 


	By:	 	 	Date: ________________, 2012


 


Henry Sicignano III


President


 


Accredited Investor


 


	By:	 	 	Date: ________________, 2012


 


Name:


Title:


 



    	2



    	 



    

 


Exhibit B


 


Form of Warrant


 



    	- 2 -



    	 



    

 


Exhibit C


 


Confidential Purchaser Questionnaire


 





22nd Century Group, Inc.


Confidential Purchaser Questionnaire


 


Before any sale of securities
by 22nd Century Group, Inc. can be made to you, this Questionnaire must be completed and returned to: 22nd Century Group, Inc.,
9530 Main Street, Clarence, New York 14031 


Attention: Henry Sicignano
III, President; Facsimile: (716) 877-3064.


 


		1.	IF YOU ARE AN INDIVIDUAL PLEASE FILL IN THE IDENTIFICATION QUESTIONS IN (A); IF YOU ARE AN ENTITY
PLEASE FILL IN THE IDENTIFICATION QUESTIONS IN (B)



 


A. INDIVIDUAL IDENTIFICATION
QUESTIONS


Name __________________________________________________________


Residence Address __________________________________________________________


Home Telephone Number (
) __________________________________________________


Fax Number ( ) __________________________________________________________


Date of Birth __________________________________________________________


Social Security Number _____________________________________________________


 


B. IDENTIFICATION QUESTIONS FOR
ENTITIES


Name ______________________________________________________________


Address of Principal

Place of Business _____________________________________________________


State (or Country) of Formation

or Incorporation ______________________________________________________


Contact Person ________________________________________________________


Telephone Number ( ) _______________________________________________________


Type of Entity

(corporation, partnership,

trust, etc.) _____________________________________________________________


Was entity formed for the purpose
of this investment?


Yes      
No ___


 


		2.	DESCRIPTION OF INVESTOR



The following
information is required to ascertain whether you would be deemed an “accredited investor” as defined in Rule 501 of
Regulation D under the Securities Act. Please check whether you are any of the following:


 


		 ̈	a corporation or partnership with total assets in excess of $5,000,000, not organized for the purpose
of this particular investment



		 ̈	private business development company as defined in Section 202(a)(22) of the Investment Advisers
Act of 1940, a U.S. venture capital fund which invests primarily through private placements in non-publicly traded securities and
makes available (either directly or through co-investors) to the portfolio companies significant guidance concerning management,
operations or business objectives



		 ̈	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



		 ̈	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



		 ̈	a trust not organized to make this particular investment, with total assets in excess of $5,000,000
whose purchase is directed by a sophisticated Person as described in Rule 506(b)(2)(ii) of the Securities Act of 1933 and
who completed item 4 below of this questionnaire



 



    	1



    	 



    

 


		 ̈	a bank as defined in Section 3(a)(2) or a savings and loan association or other institution
defined in Section 3(a)(5)(A) of the Securities Act of 1933 acting in either an individual or fiduciary capacity



		 ̈	an insurance company as defined in Section 2(13) of the Securities Act of 1933



		 ̈	an employee benefit plan within the meaning of Title I of the Employee Retirement Income Security
Act of 1974 (i) whose investment decision is made by a fiduciary which is either a bank, savings and loan association, insurance
company, or registered investment advisor, or (ii) whose total assets exceed $5,000,000, or (iii) if a self-directed
plan, whose investment decisions are made solely by a Person who is an accredited investor and who completed Part I of this
questionnaire;



		 ̈	a charitable, religious, educational or other organization described in Section 501(c)(3)
of the Internal Revenue Code, not formed for the purpose of this investment, with total assets in excess of $5,000,000



		 ̈	an entity not located in the U.S. none of whose equity owners are U.S. citizens or U.S. residents



		 ̈	a broker or dealer registered under Section 15 of the Securities Exchange Act of 1934



		 ̈	a plan having assets exceeding $5,000,000 established and maintained by a government agency for
its employees



		 ̈	an individual who had individual income from all sources during each of the last two years in excess
of $200,000 or the joint income of you and your spouse (if married) from all sources during each of such years in excess
of $300,000 and who reasonably excepts that either your own income from all sources during the current year will exceed
$200,000 or the joint income of you and your spouse (if married) from all sources during the current year will exceed $300,000



		 ̈	an individual whose net worth as of the date you purchase the securities offered, together with
the net worth of your spouse, be in excess of $1,000,000 (excluding the value of a primary residence and certain indebtedness related
thereto as set forth in footnote 1 below)1



		 ̈	an entity in which all of the equity owners are accredited investors



		 ̈	an individual or entity which is not a US Person as defined in Regulation S under the Securities
Act of 1933 (see attached Schedule A)



 


		3.	BUSINESS, INVESTMENT AND EDUCATIONAL EXPERIENCE



 


Occupation _____________________________________________________________


Number of Years _________________________________________________________


Present Employer _________________________________________________________


Position/Title ____________________________________________________________


Educational Background ____________________________________________________


 


 






1 For purposes of calculating a
person's net worth:


 


(A) The person's primary
residence shall not be included as an asset;


 


(B) Indebtedness that is
secured by the person's primary residence, up to the estimated fair market value of the primary residence at the time of the sale
of securities, shall not be included as a liability (except that if the amount of such indebtedness outstanding at the time of
sale of securities exceeds the amount outstanding 60 days before such time, other than as a result of the acquisition of the primary
residence, the amount of such excess shall be included as a liability); and


 


(C) Indebtedness that is
secured by the person's primary residence in excess of the estimated fair market value of the primary residence at the time of
the sale of securities shall be included as a liability;


 



    	2



    	 



    

 


Frequency of prior investment
(check one in each column):


 


	 	Stocks & Bonds	Venture Capital Investments
	Frequently	 	 
	Occasionally	 	 
	Never	 	 



 


		4.	SIGNATURE



 


The above information is true and correct.
The undersigned recognizes that the Company and its counsel are relying on the truth and accuracy of such information in reliance
on the exemption contained in Subsection 4(2) of the Securities Act of 1933, as amended, and Regulation D and Regulation
S promulgated thereunder. The undersigned agrees to notify the Company promptly of any changes in the foregoing information which
may occur prior to the investment.


 


Executed  at ___________________, on this
____ day of __________, 2012


 


	 	 
	 	(Signature)


 



    	3



    	 



    

Schedule A


 


“U.S. person” means:


 


(i)          Any
natural person resident in the United States;


 


(ii)         Any
partnership or corporation organized or incorporated under the laws of the United States;


 


(iii)        Any
estate of which any executor or administrator is a U.S. person;


 


(iv)        Any
trust of which any trustee is a U.S. person;


 


(v)         Any
agency or branch of a foreign entity located in the United States;


 


(vi)         Any
non-discretionary account or similar account (other than an estate or trust) held by a dealer or other fiduciary for the benefit
or account of a U.S. person;


 


(vii)        Any
discretionary account or similar account (other than an estate or trust) held by a dealer or other fiduciary organized, incorporated,
or (if an individual) resident in the United States; and


 


(viii)       Any
partnership or corporation if:


 


(A)          Organized
or incorporated under the laws of any foreign jurisdiction; and


 


(B)          Formed
by a U.S. person principally for the purpose of investing in securities not registered under the Act, unless it is organized or
incorporated, and owned, by accredited investors (as defined in Rule 501(a) under the Securities Act) who are not natural persons,
estates or trusts.


 


The following are not “U.S. persons”:


 


(i)          Any
discretionary account or similar account (other than an estate or trust) held for the benefit or account of a non-U.S. person by
a dealer or other professional fiduciary organized, incorporated, or (if an individual) resident in the United States;


 


(ii)         Any
estate of which any professional fiduciary acting as executor or administrator is a U.S. person if:


 


(A)          An
executor or administrator of the estate who is not a U.S. person has sole or shared investment discretion with respect to the assets
of the estate; and


 


(B)          The
estate is governed by foreign law;


 


(iii)        Any
trust of which any professional fiduciary acting as trustee is a U.S. person, if a trustee who is not a U.S. person has sole or
shared investment discretion with respect to the trust assets, and no beneficiary of the trust (and no settlor if the trust is
revocable) is a U.S. person;


 


(iv)         An
employee benefit plan established and administered in accordance with the law of a


country other than the United States and
customary practices and documentation of such country;


 


(v)         Any
agency or branch of a U.S. person located outside the United States if:


 


(A)          The
agency or branch operates for valid business reasons; and


 


(B)          The
agency or branch is engaged in the business of insurance or banking and is subject to substantive insurance or banking regulation,
respectively, in the jurisdiction where located; and


 


(vi)        The
International Monetary Fund, the International Bank for Reconstruction and Development, the Inter-American Development Bank, the
Asian Development Bank, the African Development Bank, the United Nations, and their agencies, affiliates and pension plans, and
any other similar international organizations, their agencies, affiliates and pension plans.


 


“United States” means
the United States of America, its territories and possessions, any State of the United States, and the District of Columbia.


 



    	4



    	 



    

 


Exhibit D


 


Selling Stockholder
Questionnaire


 


To:


22nd Century
Group, Inc.


9530 Main Street,
Clarence, New York 14031


Attention:
Henry Sicignano III, President 


Facsimile: (716)
877-3064


 


Reference is made
to the Securities Purchase Agreement (the “Agreement”), made by and among 22nd Century Group, Inc., a Nevada corporation
(the “Company”) and the Purchasers noted therein.


 


Pursuant to Section
B(12) of the Agreement, the undersigned hereby furnishes to the Company the following information for use by the Company in connection
with the preparation of the Registration Statement contemplated by Section E of the Agreement.


 


		(1)	Name and Contact Information:



			(If
                                                            you will hold Securities, as contemplated in the Agreement, through
                                                            more than one entity, whether or not affiliated, please complete a
                                                            copy of this Questionnaire for each entity.)



 


	Full legal name of record holder as it should appear in the Registration
    Statement:	 
	 	 
	Address of record holder:	 
	 	 
	Social Security Number or Taxpayer identification number of record holder:	 
	 	
	Identity of beneficial owner (if
 different than record holder):	
	 	 
	Name of contact Person:	 
	 	 
	Telephone number of contact Person:	 
	 	 
	Fax number of contact Person:	 
	 	 
	E-mail address of contact Person:	 
	 	 
	Is the record holder a publicly held entity or a subsidiary of a publicly held
    entity (i.e., an entity that has a class of securities registered under the Securities Exchange Act of 1934). 	 

        Yes £
        or No £



 



    	 



    	 



    

 


(2)        Beneficial
Ownership of Registrable Securities (i.e. shares purchased pursuant to the agreement):


 


		(a)	Number of Securities to be owned by
                                                               the Selling Stockholder:
	 	 	 
	 	 	 



 


		(b)	Number of Securities requested to
                                                               be registered:
	 	 	 
	 	 	 



 


		(3)	Beneficial Ownership
                                                                      of Other Securities of the Company Owned by the Selling
                                                                      Stockholder (i.e. shares obtained independently of the Agreement):



 


Except as set forth below in
this Item (3), the undersigned is not the beneficial or registered owner of any securities of the Company.


 


Type and amount of other securities
beneficially owned by the Selling Stockholder:


 





 



 





 



 


(4)         Relationships
with the Company:


 


Except as set forth below, neither
the undersigned nor any of its affiliates, officers, directors or principal equity holders (5% or more) has held any position
or office or has had any other material relationship with the Company (or its predecessors or affiliates) during the past three
years.


 


State any exceptions here:


 


 


 






  


 






(5)         Affiliations:


 


		(a)	Is Selling Stockholder a registered
                                                               broker-dealer?



 


 






 


		(b)	If the answer to Item 5(a) is yes,
                                                               will the Selling Stockholder receive the Registrable Securities
                                                               as compensation for underwriting activities? If yes, provide a
                                                               brief description of the transaction(s) involved.



 





 



 



    	2



    	 



    

 


		(c)	Is the Selling Stockholder an affiliate
                                                               of a registered broker-dealer(s)? (For purposes of this response,
                                                               an “affiliate” of, or Person “affiliated”
                                                               with, a specified Person is a Person that directly, or indirectly
                                                               through one or more intermediaries, controls or is controlled by,
                                                               or is under common control with, the Person specified.)



 


 






 


		(d)	If the answer to Item (5)(c) is
                                                               yes, identify the registered broker-dealer(s) and describe the
                                                               nature of the affiliation(s):



 





 



 


		(e)	If the answer to Item (5)(c) is
                                                               yes, will the Selling Stockholder acquire the Registrable Securities
                                                               in the ordinary course of business? If not, please explain.



 





 



 


		(f)	If the answer to Item (5)(c) is
                                                               yes, did the Selling Stockholder, at the time of purchase of the
                                                               Registrable Securities, have any agreements, plans or understandings,
                                                               directly or indirectly, with any Person to distribute the Registrable
                                                               Securities? If yes, please explain.



 





 



 


		(6)	Voting or Investment
                                                                      Control over the Registrable Securities:



 


If the Selling Stockholder is
not a natural Person, please identify all of the natural Person or Persons who have voting or investment control over the Registrable
Securities listed in Item (2) above and their relation to the Selling Stockholder:


 





 



 


		(7)	If you have specific
                                                                      language regarding any of the above information that you
                                                                      would like included as a footnote to the Selling Stockholder
                                                                      section of the Registration Statement, please so state (attached
                                                                      additional pages if necessary)1:



 





 



 


1No
representation is made that such language will be included in the Registration Statement in the exact form provided.


 


[The remainder of
this page has intentionally been left blank. Please continue to the following page.]


 



    	3



    	 



    

 


Pursuant to Section
E(3) of the Agreement, the undersigned acknowledges that the Company may, by notice to each Purchaser at its last known address,
suspend or withdraw the Registration Statement and require that the undersigned immediately cease sales of Registrable Securities
pursuant to the Registration Statement under certain circumstances described in the Agreement. At any time that such notice has
been given, the undersigned may not sell Registrable Securities pursuant to the Registration Statement.


 


The undersigned hereby
further acknowledges that pursuant to Section E(3)(b) of the Agreement, the undersigned shall indemnify the Company and each of
its directors and officers against, and hold the Company and each of its directors and officers harmless from, any losses, claims,
damages, expenses or liabilities (including reasonable attorneys fees) to which the Company or its directors and officers may
become subject by reason of any statement or omission in the Registration Statement made in reliance upon, or in conformity with,
a written statement by the undersigned, including the information furnished or omitted in this Questionnaire by the undersigned.


 


By signing below,
the undersigned consents to the disclosure of the information contained herein in its answers to Items (1) through (7) above and
the inclusion of such information in the Registration Statement, any amendments thereto and the related prospectus. The undersigned
understands that such information will be relied upon by the Company in connection with the preparation or amendment of the Registration
Statement and the related prospectus.


 


The undersigned has
reviewed the answers to the above questions and affirms that the same are true, complete and accurate. THE UNDERSIGNED AGREES
TO NOTIFY THE COMPANY IMMEDIATELY OF ANY CHANGES IN THE FOREGOING INFORMATION.


 


	Dated: ____________________	 
	 	Signature of Record Holder
	 	 (Please sign your name in exactly the same manner as the certificate(s)
    for the shares being registered)


 



    	4



    	 



    

 


Exhibit E


 


Anti-Money Laundering
Information Form


 





Please
complete and return this form, along with the requested documentation to: 22nd Century Group, Inc.


9530 Main Street, Clarence,
New York 14031, Attention: Henry Sicignano III, President; Facsimile: (716) 877-3064 


 


	PURCHASER NAME:	 	 
	 	 	 
	LEGAL ADDRESS:	 	 
	 	 	 
	 	 	 
	 	 	 
	SSN# or TAX ID#	 	 
	of PURCHASER:	 	 


 


IDENTIFICATION & DOCUMENTATION
AND SOURCE OF FUNDS:


 


		1.	Please submit a copy of non-expired identification for the authorized signatory(ies) on the Securities
Purchase Agreement, showing name, date of birth, address and signature. The address shown on the identification document MUST
match the Purchaser’s address as shown on the signature page to the Securities Purchase Agreement.



 


Current Driver’s License         
or            Valid Passport          or              Identity Card


(Circle one or more)


 


		2.	If the Purchaser is a corporation, limited liability company, trust or other type of entity, please
submit the following requisite documents: (i) Articles of Incorporation, By-Laws, Certificate of Formation, Operating Agreement,
Trust or other similar documents for the type of entity; and (ii) Corporate Resolution or power of attorney or other similar document
granting authority to signatory(ies) and designating that they are permitted to make the proposed investment.



 


		3.	Please advise where the funds were derived from to make the proposed investment:



 


Investments            or            Savings           or          Proceeds
of Sale             or             Other_______________


(Circle one or more)


 


Signature:__________________________


 


Print Name:__________________________


 


Title (if applicable):____________________


 


Date:________________________________