Exhibit 4.4


 





EXECUTION VERSION


 







TRANCHE 3 WARRANT


 


NEITHER THIS SECURITY NOR THE SECURITIES
FOR WHICH THIS SECURITY ARE EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION
OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES
ACT”), AND APPLICABLE STATE SECURITIES LAWS, AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO (I) AN EFFECTIVE
REGISTRATION STATEMENT UNDER THE SECURITIES ACT OR AN AVAILABLE EXEMPTION FROM, OR IN A TRANSACTION NOT SUBJECT TO, THE REGISTRATION
REQUIREMENTS OF THE SECURITIES ACT AND IN ACCORDANCE WITH APPLICABLE STATE SECURITIES LAWS AS EVIDENCED BY A LEGAL OPINION OF COUNSEL
TO THE TRANSFEROR (IF REQUESTED BY THE COMPANY) TO SUCH EFFECT, THE SUBSTANCE OF WHICH SHALL BE REASONABLY ACCEPTABLE TO THE COMPANY
OR (II) RULE 144 PROMULGATED UNDER THE SECURITIES ACT. NOTWITHSTANDING THE FOREGOING, THIS SECURITY AND THE SECURITIES ISSUABLE
UPON EXERCISE OF THIS SECURITY MAY BE PLEDGED IN CONNECTION WITH A BONA FIDE MARGIN ACCOUNT OR OTHER LOAN SECURED BY SUCH SECURITIES.


 


22ND CENTURY GROUP, INC.


 


WARRANT TO PURCHASE COMMON STOCK


 


Warrant No.:


 


Date of Issuance: September 29, 2014 (“Issuance Date”)


 


22nd Century Group, Inc., a Nevada corporation
(the “Company”), hereby certifies that, for good and valuable consideration, the receipt and sufficiency of
which are hereby acknowledged, Crede CG III, Ltd., the registered holder hereof or its permitted assigns (the “Holder”),
is entitled, subject to the terms set forth below, to purchase from the Company, at the Exercise Price (as defined below) then
in effect, upon exercise of this Warrant to Purchase Common Stock (including any Warrants to Purchase Common Stock issued in exchange,
transfer or replacement hereof, the “Warrant”), at any time or times on or after the Issuance Date but not after
11:59 p.m., New York time, on the Expiration Date (as defined below), One Million (1,000,000) (subject to adjustment as provided
herein) fully paid and non-assessable shares of Common Stock (as defined below) (the “Warrant Shares”). Except
as otherwise defined herein, capitalized terms in this Warrant shall have the meanings set forth in Section 17. This Warrant is
one of the Warrants to Purchase Common Stock (the “Consulting Warrants”) issued pursuant to that certain Consulting
Agreement, dated as of September 29, 2014, by and among the Company, Crede CG III, Ltd. and Terren Peizer (the “Consulting
Agreement”).


 






    	 



    	 



    

 


1.EXERCISE
OF WARRANT.


 


(a)Mechanics
of Exercise. Subject to the terms and conditions hereof (including, without limitation, the limitations set forth in Section
1(f)) and provided that the Vesting Condition has been met, this Warrant may be exercised by the Holder on any day on or after
the Issuance Date in whole or in part, by delivery (whether via facsimile or otherwise) of a written notice, in the form attached
hereto as Exhibit A (the “Exercise Notice”), of the Holder’s election to exercise this Warrant. Within
one (1) Trading Day following an exercise of this Warrant as aforesaid, the Holder shall deliver payment to the Company of an amount
equal to the Exercise Price in effect on the date of such exercise multiplied by the number of Warrant Shares as to which this
Warrant was so exercised (in respect of such specific exercise, the “Aggregate Exercise Price”) via wire transfer
of immediately available funds if the Holder did not notify the Company in such Exercise Notice that such exercise was made pursuant
to a Cashless Exercise (as defined in Section 1(d)). The Holder shall not be required to deliver the original of this Warrant in
order to effect an exercise hereunder. Execution and delivery of an Exercise Notice with respect to less than all of the Warrant
Shares shall have the same effect as cancellation of the original of this Warrant certificate and issuance of a new Warrant certificate
evidencing the right to purchase the remaining number of Warrant Shares. Execution and delivery of an Exercise Notice for all of
the then-remaining Warrant Shares shall have the same effect as cancellation of the original of this Warrant certificate after
delivery of the Warrant Shares in accordance with the terms hereof. On or before the first (1st) Trading Day following the later
of (i) the date on which the Company has received an Exercise Notice or (ii) the date on which the Company receives the Aggregate
Exercise Price, the Company shall transmit by facsimile an acknowledgment of confirmation of receipt of such Exercise Notice, in
the form attached hereto as Exhibit B, to the Holder and the Company’s transfer agent (the “Transfer Agent”).
On or before the second (2nd) Trading Day following the later (such later date is referred to herein as the “Delivery
Date”) of (i) the date on which the Company has received such Exercise Notice or (ii) if the Aggregate Exercise Price
is not paid by the Holder within one (1) Trading Day following such exercise as contemplated above in this Section 1(a), the date
on which the Company receives the Aggregate Exercise Price, the Company shall (X) provided that (I) the Transfer Agent is participating
in The Depository Trust Company (“DTC”) Fast Automated Securities Transfer Program and (II) such Warrant Shares
are otherwise eligible for resale pursuant to Rule 144 (as defined in the Consulting Agreement), credit such aggregate number of
shares of Common Stock to which the Holder is entitled pursuant to such exercise to the Holder’s or its designee’s
balance account with DTC through its Deposit/ Withdrawal at Custodian system, or (Y) if either of the immediately preceding clauses
(I) or (II) are not satisfied, issue and deliver to the Holder or, at the Holder’s instruction pursuant to the Exercise Notice,
the Holder’s agent or designee, in each case, sent by reputable overnight courier to the address as specified in the applicable
Exercise Notice, a certificate, registered in the Company’s share register in the name of the Holder or its designee (as
indicated in the applicable Exercise Notice), for the number of shares of Common Stock to which the Holder is entitled pursuant
to such exercise. Upon delivery of an Exercise Notice, the Holder shall be deemed for all corporate purposes to have become the
holder of record of the Warrant Shares with respect to which this Warrant has been exercised, irrespective of the date such Warrant
Shares are credited to the Holder’s DTC account or the date of delivery of the certificates evidencing such Warrant Shares
(as the case may be). If this Warrant is submitted in connection with any exercise pursuant to this Section 1(a) and the number
of Warrant Shares represented by this Warrant submitted for exercise is greater than the number of Warrant Shares being acquired
upon an exercise, then, at the request of the Holder and upon surrender hereof by the Holder at the principal office of the Company,
the Company shall as soon as practicable and in no event later than three (3) Business Days after any exercise and at its own expense,
issue and deliver to the Holder (or its designee) a new Warrant (in accordance with Section 8(d)) representing the right to purchase
the number of Warrant Shares purchasable immediately prior to such exercise under this Warrant, less the number of Warrant Shares
with respect to which this Warrant is exercised. No fractional shares of Common Stock are to be issued upon the exercise of this
Warrant, but rather the number of shares of Common Stock to be issued shall be rounded up to the nearest whole number. The Company
shall pay any and all transfer taxes and other fees which may be payable with respect to the issuance and delivery of the Warrant
Shares upon exercise of this Warrant.


 






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(b)Exercise
Price. For purposes of this Warrant, “Exercise Price” means $3.3736, subject to adjustment as provided herein.


 


(c)Company’s
Failure to Timely Deliver Securities. If the Company shall fail, for any reason or for no reason, to issue (or cause to be
issued) to the Holder on or before the applicable Delivery Date, a certificate for the number of shares of Common Stock to which
the Holder is entitled and register such shares of Common Stock on the Company’s share register or to credit the Holder’s
balance account with DTC for such number of shares of Common Stock to which the Holder is entitled upon the Holder’s exercise
of this Warrant (as the case may be), then, in addition to all other remedies available to the Holder, the Company shall pay in
cash to the Holder on each day after such third (3rd) Trading Day following the Delivery Date that the issuance of such shares
of Common Stock is not timely effected an amount equal to 1% of the product of (A) the aggregate number of shares of Common Stock
not issued to the Holder on a timely basis and to which the Holder is entitled and (B) the Closing Sale Price of the Common Stock
on the Trading Day immediately preceding the last possible date on which the Company could have issued such shares of Common Stock
to the Holder without violating Section 1(a). In addition to the foregoing, if the Company shall fail to issue and deliver (or
cause to be issued and delivered) a certificate to the Holder and register such shares of Common Stock on the Company’s share
register or to credit the Holder’s balance account with DTC for the number of shares of Common Stock to which the Holder
is entitled upon the Holder’s exercise or exchange hereunder (as the case may be) on or prior to the applicable Delivery
Date, and if on or after such Delivery Date, the Holder (or any other Person in respect, or on behalf, of the Holder) purchases
(in an open market transaction or otherwise) shares of Common Stock to deliver in satisfaction of a sale by the Holder of all or
any portion of the number of shares of Common Stock, or a sale of a number of shares of Common Stock equal to all or any portion
of the number of shares of Common Stock, issuable upon such exercise or exchange that the Holder so anticipated receiving from
the Company, then, in addition to all other remedies available to the Holder, the Company shall, in lieu of payments under the
previous sentence, within three (3) Business Days after the Holder’s request and in the Holder’s discretion, either
(i) pay cash to the Holder in an amount equal to the Holder’s total purchase price (including brokerage commissions and reasonable
out-of-pocket expenses, if any) for the shares of Common Stock so purchased (including, without limitation, by any other Person
in respect, or on behalf, of the Holder) (the “Buy-In Price”), at which point the Company’s obligation
to so issue and deliver such certificate or credit the Holder’s balance account with DTC for the number of shares of Common
Stock to which the Holder is entitled upon the Holder’s exercise or exchange hereunder (as the case may be) (and to issue
such shares of Common Stock) shall terminate, or (ii) promptly honor its obligation to so issue and deliver to the Holder a certificate
or certificates representing such shares of Common Stock or credit the Holder’s balance account with DTC for the number of
shares of Common Stock to which the Holder is entitled upon the Holder’s exercise or exchange hereunder (as the case may
be) and pay cash to the Holder in an amount equal to the excess (if any) of the Buy-In Price over the product of (A) such number
of shares of Common Stock multiplied by (B) the lowest Closing Sale Price of the Common Stock on any Trading Day during the period
commencing on the date of the applicable Exercise Notice or Exchange Notice, as the case may be, and ending on the date of such
issuance and payment under this clause (ii).


 






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(d)Cashless
Exercise. Notwithstanding anything contained herein to the contrary (other than Section 1(f) below), if at the time of an exercise
hereof an Equity Conditions Failure with respect to clauses (ii) or (iii) of the definition of Equity Conditions shall then exist,
then the Holder may, in its sole discretion, exercise this Warrant in whole or in part and, in lieu of making the cash payment
otherwise contemplated to be made to the Company upon such exercise in payment of the Aggregate Exercise Price, elect instead to
make a cashless exercise (each a “Cashless Exercise” ) under this paragraph (d). A Cashless Exercise under this
paragraph (d) may be made, at the election of the Holder from time to time and irrespective of any other election to make a Cashless
Exercise, so that upon such exercise Holder shall receive the “Net Number” of shares of Common Stock determined according
to the following formula:


 


Net Number = (A x B) - (A x C)


B


 


For purposes of the foregoing formula:


 


A = the total number of shares with respect to which this Warrant
is then being exercised.


 


B = as applicable: (i) the Closing Sale Price of the Common
Stock on the Trading Day immediately preceding the date of the applicable Exercise Notice if such Exercise Notice is (1) both executed
and delivered pursuant to Section 1(a) hereof on a day that is not a Trading Day or (2) both executed and delivered pursuant to
Section 1(a) hereof on a Trading Day prior to the opening of “regular trading hours” (as defined in Rule 600(b)(64)
of Regulation NMS promulgated under the federal securities laws) on such Trading Day or (ii) the Closing Sale Price of the Common
Stock on the date of the applicable Exercise Notice if the date of such Exercise Notice is a Trading Day and such Exercise Notice
is both executed and delivered pursuant to Section 1(a) hereof after the opening of “regular trading hours” on such
Trading Day.


 


C = the Exercise Price then in effect for the applicable Warrant
Shares at the time of such exercise.


 


Notwithstanding anything to the contrary contained herein, exercise
of this Warrant on a cashless basis may also be made from time to time at the election of the Holder (and irrespective of any election
to make a Cashless Exercise under this paragraph (d)), pursuant to the exchange provisions of Section 5 of this Warrant.


 


(e)Disputes.
In the case of a dispute as to the determination of the Exercise Price or the arithmetic calculation of the number of Warrant Shares
to be issued pursuant to the terms hereof (including, without limitation, the Net Number), the Company shall promptly issue to
the Holder the number of Warrant Shares that are not disputed, provided that following such issuance to Holder such dispute shall
be resolved in accordance with Section 14.


 






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(f)Limitations
on Exercises. Notwithstanding anything to the contrary contained in this Warrant, this Warrant shall not be exercisable by
the Holder hereof to the extent (but only to the extent) that the Holder or any of its affiliates would beneficially own in excess
of 9.9% (the “Maximum Percentage”) of the Common Stock after giving effect to such exercise. To the extent the
above limitation applies, the determination of whether this Warrant shall be exercisable (vis-à-vis other convertible, exercisable
or exchangeable securities owned by the Holder or any of its affiliates) and of which such securities shall be exercisable (as
among all such securities owned by the Holder) shall, subject to such Maximum Percentage limitation, be determined on the basis
of the first submission to the Company for conversion or exercise or exchange (as the case may be). No prior inability to exercise
this Warrant pursuant to this paragraph shall have any effect on the applicability of the provisions of this paragraph with respect
to any subsequent determination of exercisability. For the purposes of this paragraph, beneficial ownership and all determinations
and calculations (including, without limitation, with respect to calculations of percentage ownership) shall be determined in accordance
with Section 13(d) of the Securities Exchange Act of 1934, as amended (the “1934 Act”) and the rules and regulations
promulgated thereunder. The provisions of this paragraph shall be implemented in a manner otherwise than in strict conformity with
the terms of this paragraph to correct this paragraph (or any portion hereof) which may be defective or inconsistent with the intended
Maximum Percentage beneficial ownership limitation herein contained or to make changes or supplements necessary or desirable to
properly give effect to such Maximum Percentage limitation. The limitations contained in this paragraph shall apply to a successor
Holder of this Warrant. The holders of Common Stock shall be third party beneficiaries of this paragraph and the Company may not
waive this paragraph without the consent of holders of a majority of its Common Stock. For any reason at any time, upon the written
or oral request of the Holder, the Company shall within one (1) Business Day confirm orally and in writing to the Holder the number
of shares of Common Stock then outstanding, including by virtue of any prior conversion or exercise or exchange of convertible
or exercisable or exchangeable securities into Common Stock, including, without limitation, pursuant to this Warrant or securities
issued pursuant to the Consulting Agreement. Upon request by the Company, Holder shall certify to the Company upon exercise of
this Warrant how many shares of Common Stock are beneficially owned by Holder for determining compliance with this Section 1(f).


 


(g)Insufficient
Authorized Shares. The Company shall at all times keep reserved for issuance under this Warrant a number of shares of Common
Stock as shall be necessary to satisfy the Company’s obligation to issue shares of Common Stock hereunder (without regard
to any limitation otherwise contained herein with respect to the number of shares of Common Stock that may be acquirable upon exercise
of this Warrant). If, notwithstanding the foregoing, and not in limitation thereof, at any time while any of the Consulting Warrants
remain outstanding, the Company does not have a sufficient number of authorized and unreserved shares of Common Stock to satisfy
its obligation to reserve for issuance upon exercise or exchange of the Consultig Warrants at least a number of shares of Common
Stock equal to the number of shares of Common Stock as shall from time to time be necessary to effect the exercise or exchange
of all of the Consulting Warrants then outstanding (the “Required Reserve Amount”) (an “Authorized
Share Failure”), then the Company shall immediately take all action necessary to increase the Company’s authorized
shares of Common Stock to an amount sufficient to allow the Company to reserve the Required Reserve Amount for all the Consulting
Warrants then outstanding. Without limiting the generality of the foregoing sentence, as soon as practicable after the date of
the occurrence of an Authorized Share Failure, but in no event later than ninety (90) days after the occurrence of such Authorized
Share Failure, the Company shall hold a meeting of its shareholders for the approval of an increase in the number of authorized
shares of Common Stock. In connection with such meeting, the Company shall provide each shareholder with a proxy statement and
shall use its reasonable efforts to solicit its shareholders’ approval of such increase in authorized shares of Common Stock.


 






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(h)Activity
Restrictions. (i) For so long as Holder or any of its Affiliates holds any Warrants or any Warrant Shares, neither Holder nor
any Affiliate will: (i) vote any shares of Common Stock beneficially owned by it, solicit any proxies, or seek to advise or influence
any Person with respect to any voting securities of the Company; (ii) engage or participate in any actions, plans or proposals
which relate to or would result in (A) acquiring additional securities of the Company, alone or together with any other Person,
which would result in Holder or its Affiliates beneficially owning (within the meaning of Section 13(d) under the 1934 Act) more
than 9.9% of the Common Stock, (B) an extraordinary corporate transaction, such as a merger, reorganization or liquidation, involving
Company or any of its Subsidiaries, (C) a sale or transfer of a material amount of assets of the Company or any of its Subsidiaries,
(D) any change in the present board of directors or management of the Company, including any plans or proposals to change the number
or term of directors or to fill any existing vacancies on the board, (E) any material change in the present capitalization or dividend
policy of the Company, (F) any other material change in the Company’s business or corporate structure, including but not
limited to, if the Company is a registered closed-end investment company, any plans or proposals to make any changes in its investment
policy for which a vote is required by Section 13 of the Investment Company Act of 1940, (G) changes in the Company’s charter,
bylaws or instruments corresponding thereto or other actions which may impede the acquisition of control of the Company by any
Person, (H) causing a class of securities of the Company to be delisted from a national securities exchange or to cease to be authorized
to be quoted in an inter-dealer quotation system of a registered national securities association, (I) a class of equity securities
of the Company becoming eligible for termination of registration pursuant to Section 12(g)(4) of the Act, or (J) any action, intention,
plan or arrangement similar to any of those enumerated above; or (iii) request the Company or its directors, officers, employees,
agents or representatives to amend or waive any provision of this paragraph. The restrictions contained in this paragraph (h) shall
not limit Holder’s rights to enforce its rights or exercise its rights as to the Securities or under this Warrant or the
Consulting Agreement.


 


(i)Provided
that no Equity Conditions Failure then exists with respect to clause (ii) of the definition of Equity Conditions, if the trading
price on the Principal Market at the time of an exercise of this Warrant is greater than the then applicable Exercise Price then
in effect, then in respect of such particular exercise Holder may only exercise this Warrant for a cash exercise price (and not
by means of a Cashless Exercise under Section 1(d) above or on a cashless basis under Section 5 below).


 


2.ADJUSTMENT
OF EXERCISE PRICE AND NUMBER OF WARRANT SHARES. The Exercise Price and number of Warrant Shares issuable upon exercise of this
Warrant are subject to adjustment from time to time as set forth in this Section 2.


 






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(a)Stock
Dividends and Splits. If the Company, at any time on or after the Issuance Date, (i) pays a stock dividend on one or more classes
of its then outstanding shares of Common Stock or otherwise makes a distribution on any class of capital stock that is payable
in shares of Common Stock, (ii) subdivides (by any stock split, stock dividend, recapitalization or otherwise) one or more classes
of its then outstanding shares of Common Stock into a larger number of shares or (iii) combines (by combination, reverse stock
split or otherwise) one or more classes of its then outstanding shares of Common Stock into a smaller number of shares, then in
each such case the Exercise Price shall be multiplied by a fraction of which the numerator shall be the number of shares of Common
Stock outstanding immediately before such event and of which the denominator shall be the number of shares of Common Stock outstanding
immediately after such event. Any adjustment made pursuant to clause (i) of this paragraph shall become effective immediately after
the record date for the determination of shareholders entitled to receive such dividend or distribution, and any adjustment pursuant
to clause (ii) or (iii) of this paragraph shall become effective immediately after the effective date of such subdivision or combination.
If any event requiring an adjustment under this paragraph occurs during the period that an Exercise Price is calculated hereunder,
then the calculation of such Exercise Price shall be adjusted appropriately to reflect such event.


 


(b)Number
of Warrant Shares. Simultaneously with any adjustment to the Exercise Price pursuant to paragraph (a) of this Section 2, the
number of Warrant Shares that may be purchased upon exercise of this Warrant shall be increased or decreased proportionately, so
that after such adjustment the aggregate Exercise Price payable hereunder for the adjusted number of Warrant Shares shall be the
same as the aggregate Exercise Price in effect immediately prior to such adjustment (without regard to any limitations on exercise
contained herein).


 


(c)Calculations.
All calculations under this Section 2 shall be made by rounding to the nearest 1/10000th of cent and the nearest 1/100th of a share,
as applicable. The number of shares of Common Stock outstanding at any given time shall not include shares owned or held by or
for the account of the Company, and the disposition of any such shares shall be considered an issue or sale of Common Stock.


 


3.[Intentionally
Omitted].


 


4.EXTRAORDINARY
TRANSACTIONS. If, (i) the Company effects any merger or consolidation of the Company with or into another Person, (ii) the
Company effects any sale of all or substantially all of its assets in one or a series of related transactions, (iii) any tender
offer or exchange offer by the Company is completed pursuant to which holders of Common Stock are permitted to tender or exchange
their shares for other securities, cash or property, or (iv) the Company effects any reclassification of the Common Stock or any
compulsory share exchange pursuant to which the Common Stock is effectively converted into or exchanged for other securities, cash
or property (in any such case, an “Extraordinary Transaction”), then this Warrant will become the right thereafter
to receive, upon exercise, the same amount and kind of securities, cash or property as the Holder would have been entitled to receive
upon the occurrence of such Extraordinary Transaction if it had been, immediately prior to such Extraordinary Transaction, the
holder of the number of Warrant Shares then issuable upon exercise in full of the relevant Warrant (the “Alternate Consideration”)
in lieu of Common Stock. The aggregate Exercise Price for each Warrant will not be affected by any such Extraordinary Transaction,
but the Company shall apportion such aggregate Exercise Price among the Alternate Consideration in a reasonable manner reflecting
the relative value of any different components of the Alternate Consideration. If holders of Common Stock are given any choice
as to the securities, cash or property to be received in an Extraordinary Transaction, then the Holder, to the extent practicable,
shall be given the same choice as to the Alternate Consideration it receives upon any exercise of its Warrant following such Extraordinary
Transaction. In addition, at the request of the Holder, upon surrender of this Warrant, any successor to the Company or surviving
entity in such Extraordinary Transaction shall issue to such Holder a new warrant consistent with the foregoing provisions and
evidencing the Holder’s right to purchase the Alternate Consideration for the aggregate Exercise Price upon exercise thereof.
Each such new warrant (or any such replacement security) will be similarly adjusted upon any subsequent transaction analogous to
an Extraordinary Transaction.


 






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5.[Intentionally
Omitted.]


 


6.NONCIRCUMVENTION.
The Company hereby covenants and agrees that the Company will not, by amendment of its Certificate of Incorporation, Bylaws or
through any reorganization, transfer of assets, consolidation, merger, scheme of arrangement, dissolution, issue or sale of securities,
or any other voluntary action, for the purpose of avoiding or seeking to avoid the observance or performance of any of the terms
of this Warrant, and will at all times in good faith carry out all the provisions of this Warrant and take all action as may be
required to protect the rights of the Holder. Without limiting the generality of the foregoing, the Company (i) shall not increase
the par value of any shares of Common Stock receivable upon the exercise of this Warrant above the Exercise Price then in effect,
(ii) shall take all such actions as may be necessary or appropriate in order that the Company may validly and legally issue fully
paid and non-assessable shares of Common Stock upon the exercise of this Warrant (or such other securities, cash, assets or other
property then deliverable on exercise of this Warrant), and (iii) shall, so long as any of the Consulting Warrants are outstanding,
take all action necessary to reserve and keep available out of its authorized and unissued shares of Common Stock, solely for the
purpose of effecting the exercise of the Consulting Warrants, the maximum number of shares of Common Stock as shall from time to
time be necessary to effect the exercise of the Consulting Warrants then outstanding (without regard to any limitations on exercise).


 


7.WARRANT
HOLDER NOT DEEMED A STOCKHOLDER. Except as otherwise specifically provided herein, the Holder, solely in its capacity as a
holder of this Warrant, shall not be entitled to vote or receive dividends or be deemed the holder of share capital of the Company
for any purpose, nor shall anything contained in this Warrant be construed to confer upon the Holder, solely in its capacity as
the Holder of this Warrant, any of the rights of a stockholder of the Company or any right to vote, give or withhold consent to
any corporate action (whether any reorganization, issue of stock, reclassification of stock, consolidation, merger, conveyance
or otherwise), receive notice of meetings, receive dividends or subscription rights, or otherwise, prior to the issuance to the
Holder of the Warrant Shares which it is then entitled to receive upon the due exercise of this Warrant. In addition, nothing contained
in this Warrant shall be construed as imposing any liabilities on the Holder to purchase any securities (upon exercise of this
Warrant or otherwise) or as a stockholder of the Company, whether such liabilities are asserted by the Company or by creditors
of the Company. Notwithstanding this Section 7, the Company shall provide the Holder with copies of the same notices and other
information given to the stockholders of the Company generally, contemporaneously with the giving thereof to the stockholders;
provided that the Company shall not be obligated to provide such information if it is filed with the SEC through EDGAR and
available to the public through the EDGAR system.


 






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8.REISSUANCE
OF WARRANTS.


 


(a)Transfer
of Warrant. If this Warrant is to be transferred, the Holder shall surrender this Warrant to the Company, whereupon the Company
will forthwith issue and deliver upon the order of the Holder a new Warrant (in accordance with Section 8(d)), registered as the
Holder may request, representing the right to purchase the number of Warrant Shares being transferred by the Holder and, if less
than the total number of Warrant Shares then underlying this Warrant is being transferred, a new Warrant (in accordance with Section
8(d)) to the Holder representing the right to purchase the number of Warrant Shares not being transferred. Prior to transferring
this Warrant, the Holder shall inform the transferee of the total number of Warrant Shares then underlying this Warrant.


 


(b)Lost,
Stolen or Mutilated Warrant. Upon receipt by the Company of evidence reasonably satisfactory to the Company of the loss, theft,
destruction or mutilation of this Warrant (as to which a written certification and the indemnification contemplated below shall
suffice as such evidence), and, in the case of loss, theft or destruction, of any indemnification undertaking by the Holder to
the Company in customary and reasonable form and, in the case of mutilation, upon surrender and cancellation of this Warrant, the
Company shall execute and deliver to the Holder a new Warrant (in accordance with Section 8(d)) representing the right to purchase
the Warrant Shares then underlying this Warrant.


 


(c)Exchangeable
for Multiple Warrants. This Warrant is exchangeable, upon the surrender hereof by the Holder at the principal office of the
Company, for a new Warrant or Warrants (in accordance with Section 8(d)) representing in the aggregate the right to purchase the
number of Warrant Shares then underlying this Warrant, and each such new Warrant will represent the right to purchase such portion
of such Warrant Shares as is designated by the Holder at the time of such surrender; provided, however, no warrants for fractional
shares of Common Stock shall be given.


 


(d)Issuance
of New Warrants. Whenever the Company is required to issue a new Warrant pursuant to the terms of this Warrant, such new Warrant
(i) shall be of like tenor with this Warrant, (ii) shall represent, as indicated on the face of such new Warrant, the right to
purchase the Warrant Shares then underlying this Warrant (or in the case of a new Warrant being issued pursuant to Section 8(a)
or Section 8(c), the Warrant Shares designated by the Holder which, when added to the number of shares of Common Stock underlying
the other new Warrants issued in connection with such issuance, does not exceed the number of Warrant Shares then underlying this
Warrant), (iii) shall have an issuance date, as indicated on the face of such new Warrant which is the same as the Issuance Date,
and (iv) shall have the same rights and conditions as this Warrant.


 






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9.NOTICES.
Whenever notice is required to be given under this Warrant, unless otherwise provided herein, such notice shall be given in accordance
with Section 10 of the Consulting Agreement. The Company shall provide the Holder with prompt written notice of all actions taken
pursuant to this Warrant, including in reasonable detail a description of such action and the reason therefor. Without limiting
the generality of the foregoing, the Company will give written notice to the Holder (i) as soon as practicable upon each adjustment
of the Exercise Price and the number of Warrant Shares, setting forth in reasonable detail, and certifying, the calculation of
such adjustment(s). If the Company (i) declares a dividend or any other distribution of cash, securities or other property in respect
of its Common Stock (other than a dividend payable solely in shares of Common Stock) or (ii) authorizes the voluntary dissolution,
liquidation or winding up of the affairs of the Company, then the Company shall deliver to each Holder a notice describing the
material terms and conditions of such dividend, distribution or transaction. Notwithstanding anything to the contrary in this Section
9, the failure to deliver any notice under this Section 9 or any defect therein shall not affect the validity of the corporate
action required to be described in such notice. Until the exercise of its, his or her Warrant or any portion of such Warrant, a
Holder shall not have nor exercise any rights by virtue of ownership of a Warrant as a shareholder of the Company (including without
limitation the right to notification of shareholder meetings or the right to receive any notice or other communication concerning
the business and affairs of the Company other than as provided in this Section 9.


 


10.AMENDMENT
AND WAIVER. Except as otherwise provided herein, the provisions of this Warrant (other than Section 1(f)) may be amended and
the Company may take any action herein prohibited, or omit to perform any act herein required to be performed by it, only if the
Company has obtained the written consent of the Holder. No waiver shall be effective unless it is in writing and signed by an authorized
representative of the waiving party. The Holder shall be entitled, at its option, to the benefit of any amendment of any other
similar warrant issued under the Consulting Agreement.


 


11.SEVERABILITY.
If any provision of this Warrant is prohibited by law or otherwise determined to be invalid or unenforceable by a court of competent
jurisdiction, the provision that would otherwise be prohibited, invalid or unenforceable shall be deemed amended to apply to the
broadest extent that it would be valid and enforceable, and the invalidity or unenforceability of such provision shall not affect
the validity of the remaining provisions of this Warrant so long as this Warrant as so modified continues to express, without material
change, the original intentions of the parties as to the subject matter hereof and the prohibited nature, invalidity or unenforceability
of the provision(s) in question does not substantially impair the respective expectations or reciprocal obligations of the parties
or the practical realization of the benefits that would otherwise be conferred upon the parties. The parties will endeavor in good
faith negotiations to replace the prohibited, invalid or unenforceable provision(s) with a valid provision(s), the effect of which
comes as close as possible to that of the prohibited, invalid or unenforceable provision(s).


 


12.GOVERNING
LAW. This Warrant shall be governed by and construed and enforced in accordance with, and all questions concerning the construction,
validity, interpretation and performance of this Warrant shall be governed by, the internal laws of the State of New York, without
giving effect to any choice of law or conflict of law provision or rule (whether of the State of New York or any other jurisdictions)
that would cause the application of the laws of any jurisdictions other than the State of New York. Each of the Holder and the
Company hereby irrevocably submits to the exclusive jurisdiction of the state and federal courts sitting in The City of New York,
Borough of Manhattan, for the adjudication of any dispute hereunder or in connection herewith or with any transaction contemplated
hereby or discussed herein, 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. Nothing contained herein shall be deemed to
limit in any way any right to serve process in any manner permitted by law. Nothing contained herein shall be deemed or operate
to preclude either the Holder or the Company from bringing suit or taking other legal action against the Holder or the Company
in any other jurisdiction to enforce a judgment or other court ruling in favor of the Holder or the Company. EACH OF THE HOLDER
AND THE COMPANY HEREBY IRREVOCABLY WAIVES ANY RIGHT IT MAY HAVE TO, AND AGREES NOT TO REQUEST, A JURY TRIAL FOR THE ADJUDICATION
OF ANY DISPUTE HEREUNDER OR IN CONNECTION WITH OR ARISING OUT OF THIS WARRANT OR ANY TRANSACTION CONTEMPLATED HEREBY.


 






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13.CONSTRUCTION;
HEADINGS. This Warrant shall be deemed to be jointly drafted by the Company and the Holder and shall not be construed against
any Person as the drafter hereof. The headings of this Warrant are for convenience of reference and shall not form part of, or
affect the interpretation of, this Warrant. Terms used in this Warrant but defined in the Consulting Agreement shall have the meanings
ascribed to such terms in the Consulting Agreement unless otherwise consented to in writing by the Holder.


 


14.DISPUTE
RESOLUTION. In the case of a dispute as to the determination of the Exercise Price, the Closing Sale Price, the fair market
value or the arithmetic calculation of the Warrant Shares (as the case may be), the Company or the Holder (as the case may be)
may submit the disputed determinations or arithmetic calculations (as the case may be) via facsimile (i) within two (2) Business
Days after receipt of the applicable notice giving rise to such dispute to the Company or the Holder (as the case may be) or (ii)
if no notice gave rise to such dispute, at any time after the Holder or the Company (as the case may be) learned of the circumstances
giving rise to such dispute. If the Holder and the Company are unable to agree upon such determination or calculation (as the case
may be) of the Exercise Price, the Closing Sale Price, the fair market value or the number of Warrant Shares (as the case may be)
within three (3) Business Days of such disputed determination or arithmetic calculation being submitted to the Company or the Holder
(as the case may be), then the Company shall, within two (2) Business Days submit via facsimile (a) the disputed arithmetic calculation
of the Warrant Shares, the disputed determination of the Exercise Price, the Closing Sale Price, the fair market value (as the
case may be) to an independent, reputable investment bank of nationally recognized standing selected by the Holder and reasonably
acceptable to the Company or (b) if acceptable to the Holder, the disputed arithmetic calculation of the Warrant Shares to the
Company’s independent, outside accountant. The Company shall use its commercially reasonable efforts to cause at its expense
the investment bank or the accountant (as the case may be) to perform the determinations or calculations (as the case may be) and
notify the Company and the Holder of the results no later than ten (10) Business Days from the time it receives such disputed determinations
or calculations (as the case may be). Such investment bank’s or accountant’s determination or calculation (as the case
may be) shall be binding upon all parties absent demonstrable error. The party whose determination or calculation is furthest from
that determined or calculation by the investment bank or accountant shall pay the costs of such determination or calculation.


 






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15.REMEDIES,
CHARACTERIZATION, OTHER OBLIGATIONS, BREACHES AND INJUNCTIVE RELIEF. The remedies provided in this Warrant shall be cumulative
and in addition to all other remedies available under this Warrant and the Consulting Agreement, at law or in equity (including
a decree of specific performance and/or other injunctive relief), and nothing herein shall limit the right of the Holder to pursue
actual and consequential damages for any failure by the Company to comply with the terms of this Warrant; provided, however, that
Holder’s remedies, including any right of damages, shall be subject to Section 9(k) of the Securities Purchase Agreement
dated September 17, 2014 between Holder and the Company. The Company covenants to the Holder that there shall be no characterization
concerning this instrument other than as expressly provided herein. Amounts set forth or provided for herein with respect to payments,
exercises and the like (and the computation thereof) shall be the amounts to be received by the Holder and shall not, except as
expressly provided herein, be subject to any other obligation of the Company (or the performance thereof). The Company acknowledges
that a breach by it of its obligations hereunder will cause irreparable harm to the Holder and that the remedy at law for any such
breach may be inadequate. The Company therefore agrees that, in the event of any such breach or threatened breach, the holder of
this Warrant shall be entitled, in addition to all other available remedies, to an injunction restraining any breach, without the
necessity of showing economic loss and without any bond or other security being required. The Company shall provide all information
and documentation to the Holder that is reasonably requested by the Holder to enable the Holder to confirm the Company’s
compliance with the terms and conditions of this Warrant (including, without limitation, compliance with Section 2 hereof). The
issuance of shares and certificates for shares as contemplated hereby upon the exercise of this Warrant shall be made without charge
to the Holder or such shares for any issuance or stamp tax or other costs in respect thereof, provided that the Company shall not
be required to pay any tax which may be payable in respect of any transfer involved in the issuance and delivery of any certificate
in a name other than the Holder or its agent on its behalf.


 


16.TRANSFER.
This Warrant may be offered for sale, sold, transferred or assigned without the consent of the Company.


 


17.CERTAIN
DEFINITIONS. For purposes of this Warrant, the following terms shall have the following meanings:


 


(a)“Bloomberg”
means Bloomberg, L.P.


 


(b)“Business
Day” means any day other than Saturday, Sunday or other day on which commercial banks in The City of New York are authorized
or required by law to remain closed.


 


(c)“Common
Stock” means (i) the Company’s shares of common stock, $0.001 par value per share, and (ii) any capital stock into
which such common stock shall have been changed or any share capital resulting from a reclassification of such common stock.


 






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(d)“Convertible
Securities” means any stock or other security (other than Options) that is at any time and under any circumstances, directly
or indirectly, convertible into, exercisable or exchangeable for, or which otherwise entitles the holder thereof to acquire, any
shares of Common Stock.


 


(e)“Equity
Conditions” means: (i) the Company shall be in compliance in all material respects with all of its obligations under
the Consulting Agreement, (ii) all Common Shares and Warrant Shares (including any Warrant Shares to be received upon exercise
of this Warrant and including any Warrant Shares to be issued in a cash exercise) shall be then, or upon such issuance shall be
(as the case may be), freely tradable by Holder without restriction of any kind or nature (including, without limitation, under
applicable securities laws) (and the Company shall have no knowledge of any fact which would reasonably be expected to negate the
foregoing in the foreseeable future) other than restrictions that may result from the Holder being an “affiliate” of
the Company as defined in Rule 144 promulgated under the 1933 Act or under Rule 144(i), and (iii) no limitation shall be applicable
with respect to the issuance of any Warrant Shares for cash hereunder (other than under Section 1(f)).


 


(f)“Equity
Conditions Failure” means that on any applicable date of determination, any of the Equity Conditions are not then satisfied.


 


(g)“Expiration
Date” means the date that is the fifth (5th) anniversary of the Issuance Date or, if such date falls on a day other than
a Business Day or on which trading does not take place on the Principal Market (a “Holiday”), the next date that is
not a Holiday.


 


(h)“Options”
means any rights, warrants or options to subscribe for or purchase shares of Common Stock or Convertible Securities.


 


(i)“Person”
means an individual, a limited liability company, a partnership, a joint venture, a corporation, a trust, an unincorporated organization,
any other entity or a government or any department or agency thereof.


 


(j)“Principal
Market” means the NYSE MKT.


 


(k)“Trading
Day” means, as applicable, (x) with respect to all price determinations relating to the Common Stock, any day on which
the Common Stock is traded on the Principal Market, or, if the Principal Market is not the principal trading market for the Common
Stock, then on the principal securities exchange or securities market on which the Common Stock is then traded, provided that “Trading
Day” shall not include any day on which the Common Stock is scheduled to trade on such exchange or market for less than 4.5
hours or any day that the Common Stock is suspended from trading during the final hour of trading on such exchange or market (or
if such exchange or market does not designate in advance the closing time of trading on such exchange or market, then during the
hour ending at 4:00:00 p.m., New York time) or (y) with respect to all determinations other than price determinations relating
to the Common Stock, any day on which The New York Stock Exchange (or any successor thereto) is open for trading of securities.


 






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(l)“Vesting
Condition” means either (i) the China JV (as defined in the Consulting Agreement) has achieved revenues calculated in
accordance with United States generally accepted accounting principles (“GAAP”) applied on a consistent basis in an
amount equal to at least Forty-Five Million United States Dollars (US$45,000,000.00) during either (A) the 12 month period commencing
on the earlier of (x) January 1, 2016 if the tobacco provided to China Tobacco has been evaluated and approved for sale no later
than December 31, 2014; (y) the date that tobacco purchases are first made by China Tobacco from the China JV or (z) January 1,
2017 (the “Commencement Date”), (B) the 12 month period beginning on the first anniversary of the Commencement
Date or (C) the 12 month period beginning on the second anniversary of the Commencement Date from sales by the China JV for the
market in China of the proprietary tobacco of the Company (the “Tranche 3 Minimum Triggering Revenue”) and the
Company thereafter receives a cash distribution from the China JV so that the Company is “cash flow positive for the Company’s
investment in the China JV,” which means the positive difference between all United States Dollars that the Company has received
in relation to the China JV, including any licensing revenue, minus all United States Dollars that the Company has paid out in
relation to the China JV, including the money paid by the Company for the first major tobacco planting by the Company for sale
to the China JV, all to be described in greater detail in the China JV agreements to be entered into between the Company and the
China JV; or (ii) the China JV has achieved revenues calculated in accordance with GAAP in an amount equal to at least Twenty-Seven
Million United States Dollars (US$27,000,000.00) during either of the 12 month periods beginning on the Commencement Date and the
first anniversary of the Commencement Date from sales by the China JV for the market in China of the proprietary tobacco of the
Company (the “Tranche 3 Alternative Triggering Revenue”) and the Company thereafter receives a cash distribution
from the China JV so that the Company is “cash flow positive for the Company’s investment in the China JV,” which
means the positive difference between all United States Dollars that the Company has received in relation to the China JV, including
any licensing revenue and an appropriate distribution to the Company from the China JV for first major tobacco planting by the
Company for sale to the China JV as described above, minus all United States Dollars that the Company has paid out in relation
to the China JV for the second major tobacco planting, all to be described in greater detail in the China JV agreements to be entered
into between the Company and the China JV.


 


(m)“Voting
Stock” of a Person means capital stock of such Person of the class or classes pursuant to which the holders thereof have
the general voting power to elect, or the general power to appoint, at least a majority of the board of directors, managers or
trustees of such Person (irrespective of whether or not at the time capital stock of any other class or classes shall have or might
have voting power by reason of the happening of any contingency).


 


18.REDEMPTION.


 


(a)Redemption
of Warrant. So long as there is No Equity Conditions Failure, this Warrant may be redeemed, in whole or in part, at
the option of the Company, at any time after it becomes exercisable and prior to its expiration, at the office of the Company upon
the notice referred to in Section 9 hereof, at the price equal to 130% of the Exercise Price (the “Redemption Price”).


 


(b)Date
Fixed for, and Notice of, Redemption. In the event the Company shall elect to redeem the Warrant, the Company shall
fix a date for the redemption. Notice of redemption shall be mailed by overnight mail next day delivery, by the Company not less
than fifteen (15) days prior to the date fixed for redemption to the Holder of the Warrant to be redeemed at their last addresses
as they shall appear on the registration books.


 






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(c)Exercise
After Notice of Redemption. The Warrant may be exercised in accordance with this Warrant at any time after notice of redemption
shall have been given by the Company and prior to the time and date fixed for redemption. On and after the redemption date, the
Registered Holder shall have no further rights except to receive, upon surrender of the Warrants, the Redemption Price.


 


[signature page follows]


 







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IN WITNESS WHEREOF, the Company has
caused this Warrant to Purchase Common Stock to be duly executed as of the Issuance Date set out above.


 


22ND CENTURY GROUP, INC.


 








	By:	 	 
	Name:		 
	Title:		 





 




    	 



    	 



    

 


EXHIBIT A


 


EXERCISE NOTICE


 


TO BE EXECUTED BY THE REGISTERED HOLDER
TO EXERCISE THIS


WARRANT TO PURCHASE COMMON STOCK


 


22ND CENTURY GROUP, INC.


 


The undersigned holder hereby exercises
the right to purchase               of the shares of Common Stock (“Warrant Shares”) of 22nd Century Group, Inc., a Nevada
corporation (the “Company”), evidenced by Warrant to Purchase Common Stock No.                (the “Warrant”).
Capitalized terms used herein and not otherwise defined shall have the respective meanings set forth in the Warrant.


 


1.Form of Exercise Price. The
Holder intends that payment of the Exercise Price shall be made as:


 





	 	 	a “Cash Exercise” with respect to ______________ Warrant Shares; and/or
	 	 	 
	 	 	a “Cashless Exercise” with respect to ___________ Warrant Shares.





 


In the event that the Holder has elected
a Cashless Exercise with respect to some or all of the Warrant Shares to be issued pursuant hereto, the Holder hereby represents
and warrants that this Exercise Notice was executed by the Holder at [a.m.][p.m.] on the date set forth below.


 


2.The undersigned represents and warrants
that the Holder is an “accredited investor” as that term is defined in Rule 501(a) of Regulation D.


 


3.Payment of Exercise Price.
In the event that the Holder has elected a Cash Exercise with respect to some or all of the Warrant Shares, the Holder shall pay
the Aggregate Exercise Price in the sum of $              to the Company in accordance with the terms of the Warrant.


 


4.Delivery of Warrant Shares and
Net Number of shares of Common Stock. The Company shall deliver to Holder, or its designee or agent as specified below,               shares
of Common Stock in respect of the exercise contemplated hereby. Delivery shall be made to Holder, or for its benefit, to the following
address:


 











	 	 	 
	 	 	 
	 	 	 
	 	 	 
	 	 	 
	 	 	 


 








	Date:		 
	 	 	 
		Name of Registered Holder


 





	By:  	 	 
		Name:	 
		Title:	 





 





	Account	 
	Number:  	
		(if electronic book entry transfer)


 





	Transaction Code
	Number:  	 
		(if electronic book entry transfer)