Document:

REGISTRATION
RIGHTS AGREEMENT

 

This
Registration Rights Agreement (this “Agreement”) is made and entered into as of January 11, 2013, between 22nd
Century Group, Inc., a Nevada corporation (the “Company”), and each of the several purchasers signatory
hereto (each such purchaser, a “Purchaser” and, collectively, the “Purchasers”).

 

This
Agreement is made pursuant to the Securities Purchase Agreement, dated as of the date hereof, between the Company and each Purchaser
(the “Purchase Agreement”).

 

The
Company and each Purchaser hereby agrees as follows:

 

		1.	Definitions.

 

Capitalized
terms used and not otherwise defined herein that are defined in the Purchase Agreement shall have the meanings given such terms
in the Purchase Agreement. As used in this Agreement, the following terms shall have the following meanings:

 

“Advice”
shall have the meaning set forth in Section 6(d).

 

“Effectiveness
Date” means, with respect to the Initial Registration Statement required to be filed hereunder, the 60th
calendar day following the date hereof (or, in the event of a review by the Commission, the 105th calendar day following
the date hereof) and with respect to any additional Registration Statements which may be required pursuant to Section 2(c) or
Section 3(c), the 60th calendar day following the date on which an additional Registration Statement is required to
be filed hereunder (or, in the event of a review by the Commission, the 105th calendar day following the date such
additional Registration Statement is required to be filed hereunder); provided, however, that in the event the Company
is notified by the Commission that one or more of the above Registration Statements will not be reviewed or is no longer subject
to further review and comments, the Effectiveness Date as to such Registration Statement shall be the fifth Trading Day following
the date on which the Company is so notified if such date precedes the dates otherwise required above, provided, further, if such
Effectiveness Date falls on a day that is not a Trading Day, then the Effectiveness Date shall be the next succeeding Trading
Day.

 

“Effectiveness
Period” shall have the meaning set forth in Section 2(a).

 

“Event”
shall have the meaning set forth in Section 2(d).

 

“Event
Date” shall have the meaning set forth in Section 2(d).

 

    	 

    	 

    

 

“Filing
Date” means, with respect to the Initial Registration Statement required hereunder, the 30th calendar day
following the date hereof and, with respect to any additional Registration Statements which may be required pursuant to Section
2(c) or Section 3(c), the earliest practical date on which the Company is permitted by SEC Guidance to file such additional Registration
Statement related to the Registrable Securities.

 

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

 

“Indemnified
Party” shall have the meaning set forth in Section 5(c).

 

“Indemnifying
Party” shall have the meaning set forth in Section 5(c).

 

“Initial
Registration Statement” means the initial Registration Statement filed pursuant to this Agreement.

 

“Losses”
shall have the meaning set forth in Section 5(a).

 

“Plan
of Distribution” shall have the meaning set forth in Section 2(a).

 

“Prospectus”
means the prospectus included in a Registration Statement (including, without limitation, a prospectus that includes any information
previously omitted from a prospectus filed as part of an effective registration statement in reliance upon Rule 430A promulgated
by the Commission pursuant to the Securities Act), as amended or supplemented by any prospectus supplement, with respect to the
terms of the offering of any portion of the Registrable Securities covered by a Registration Statement, and all other amendments
and supplements to the Prospectus, including post-effective amendments, and all material incorporated by reference or deemed to
be incorporated by reference in such Prospectus.

 

    	2

    	 

    

 

“Registrable
Securities” means, as of any date of determination, (a) all of the shares of Common Stock then issuable upon conversion
in full of the Preferred Stock (assuming on such date the shares of Preferred Stock are converted in full without regard to any
conversion limitations therein), (b) all shares of Common Stock issuable as dividends on the Preferred Stock assuming all dividend
payments are made in shares of Common Stock and the Preferred Stock is held for at least 3 years, (c) all Warrant Shares then
issuable upon exercise of the Warrants (assuming on such date the Warrants are exercised in full without regard to any exercise
limitations therein), (d) any additional shares of Common Stock issuable in connection with any anti-dilution provisions in the
Preferred Stock or the Warrants (in each case, without giving effect to any limitations on conversion set forth in the Certificate
of Designation or limitations on exercise set forth in the Warrants) and (e) any securities issued or then issuable upon any stock
split, dividend or other distribution, recapitalization or similar event with respect to the foregoing; provided, however,
that any such Registrable Securities shall cease to be Registrable Securities (and the Company shall not be required to maintain
the effectiveness of any, or file another, Registration Statement hereunder with respect thereto) for so long as (a) a Registration
Statement with respect to the sale of such Registrable Securities is declared effective by the Commission under the Securities
Act and such Registrable Securities have been disposed of by the Holder in accordance with such effective Registration Statement,
(b) such Registrable Securities have been previously sold in accordance with Rule 144, or (c) such securities become eligible
for resale without volume or manner-of-sale restrictions and without current public information pursuant to Rule 144 as set forth
in a written opinion letter to such effect, addressed, delivered and acceptable to the Transfer Agent and the affected Holders
(assuming that such securities and any securities issuable upon exercise, conversion or exchange of which, or as a dividend upon
which, such securities were issued or are issuable, were at no time held by any Affiliate of the Company, and all Warrants are
exercised by “cashless exercise” as provided in Section 2(c) of each of the Warrants), as reasonably determined by
the Company, upon the advice of counsel to the Company.

 

“Registration
Statement” means any registration statement required to be filed hereunder pursuant to Section 2(a) and any additional
registration statements contemplated by Section 2(c) or Section 3(c), including (in each case) the Prospectus, amendments and
supplements to any such registration statement or Prospectus, including pre- and post-effective amendments, all exhibits thereto,
and all material incorporated by reference or deemed to be incorporated by reference in any such registration statement.

 

“Rule
415” means Rule 415 promulgated by the Commission pursuant to the Securities Act, as such Rule may be amended or interpreted
from time to time, or any similar rule or regulation hereafter adopted by the Commission having substantially the same purpose
and effect as such Rule.

 

“Rule
424” means Rule 424 promulgated by the Commission pursuant to the Securities Act, as such Rule may be amended or interpreted
from time to time, or any similar rule or regulation hereafter adopted by the Commission having substantially the same purpose
and effect as such Rule.

 

“Selling
Stockholder Questionnaire” shall have the meaning set forth in Section 3(a).

 

“SEC
Guidance” means (i) any publicly-available written or oral guidance of the Commission staff, or any comments, requirements
or requests of the Commission staff and (ii) the Securities Act.

 

    	3

    	 

    

 

		2.	Shelf
                                                                                 Registration.

 

(a)          On
or prior to each Filing Date, the Company shall prepare and file with the Commission a Registration Statement covering the resale
of 200% of the Registrable Securities that are not then registered on an effective Registration Statement for an offering to be
made on a continuous basis pursuant to Rule 415. Each Registration Statement filed hereunder shall be on Form S-1 (except if the
Company is not then eligible to register for resale the Registrable Securities on Form S-1, in which case such registration shall
be on another appropriate form in accordance herewith, subject to the provisions of Section 2(e)) and shall contain (unless otherwise
directed by at least 85% in interest of the Holders) substantially the “Plan of Distribution” attached hereto
as Annex A. Subject to the terms of this Agreement, the Company shall use its best efforts to cause a Registration Statement
filed under this Agreement (including, without limitation, under Section 3(c)) to be declared effective under the Securities Act
as promptly as possible after the filing thereof, but in any event no later than the applicable Effectiveness Date, and shall
use its best efforts to keep such Registration Statement continuously effective under the Securities Act until all Registrable
Securities covered by such Registration Statement (i) have been sold, thereunder or pursuant to Rule 144, or (ii) may be sold
without volume or manner-of-sale restrictions pursuant to Rule 144 and without the requirement for the Company to be in compliance
with the current public information requirement under Rule 144, as determined by the counsel to the Company pursuant to a written
opinion letter to such effect, addressed and acceptable to the Transfer Agent and the affected Holders (the “Effectiveness
Period”). The Company shall request effectiveness of a Registration Statement as of 5:00 p.m. Eastern Time on a Trading
Day. The Company shall immediately notify the Holders via facsimile or by e-mail of the effectiveness of a Registration Statement
on the same Trading Day that the Company confirms effectiveness with the Commission, which shall be the date requested for effectiveness
of such Registration Statement. Failure to so notify the Holder within one (1) Trading Day of such notification of effectiveness
or failure to file a final Prospectus as foresaid shall be deemed an Event under Section 2(d).

 

(b)          
Notwithstanding the registration obligations set forth in Section 2(a), if the Commission informs the Company that all of the
Registrable Securities cannot, as a result of the application of Rule 415, be registered for resale as a secondary offering on
a single registration statement, the Company agrees to promptly inform each of the Holders thereof and use its commercially reasonable
efforts to file amendments to the Initial Registration Statement as required by the Commission, covering the maximum number of
Registrable Securities permitted to be registered by the Commission, on Form S-1 or such other form available to register for
resale the Registrable Securities as a secondary offering, subject to the provisions of Section 2(e); provided, however,
that prior to filing such amendment, the Company shall be obligated to use diligent efforts to advocate with the Commission for
the registration of all of the Registrable Securities in accordance with the SEC Guidance, including without limitation, Compliance
and Disclosure Interpretation 612.09.

 

    	4

    	 

    

 

(c)          Notwithstanding
any other provision of this Agreement and subject to the payment of liquidated damages pursuant to Section 2(d), if the Commission
or any SEC Guidance sets forth a limitation on the number of Registrable Securities permitted to be registered on a particular
Registration Statement as a secondary offering (and notwithstanding that the Company used diligent efforts to advocate with the
Commission for the registration of all or a greater portion of Registrable Securities), unless otherwise directed in writing by
a Holder as to its Registrable Securities, the number of Registrable Securities to be registered on such Registration Statement
will be reduced as follows: 

 

		a.	First,
                                                                the Company shall reduce Registrable Securities represented by
                                                                Warrant Shares (applied, in the case that some Warrant Shares
                                                                may be registered, to the Holders on a pro rata basis based on
                                                                the total number of unregistered Warrant Shares held by such Holders);
                                                                and

 

		b.	Second,
                                                                the Company shall reduce Registrable Securities represented by
                                                                Conversion Shares (applied, in the case that some Conversion Shares
                                                                may be registered, to the Holders on a pro rata basis based on
                                                                the total number of unregistered Conversion Shares held by such
                                                                Holders).

 

In
the event of a cutback hereunder, the Company shall give the Holder at least five (5) Trading Days prior written notice along
with the calculations as to such Holder’s allotment. In the event the Company amends the Initial Registration Statement
in accordance with the foregoing, the Company will use its best efforts to file with the Commission, as promptly as allowed by
Commission or SEC Guidance provided to the Company or to registrants of securities in general, one or more registration statements
on Form S-1 or such other form available to register for resale those Registrable Securities that were not registered for resale
on the Initial Registration Statement, as amended.

 

    	5

    	 

    

 

(d)          If:
(i) the Initial Registration Statement is not filed on or prior to its Filing Date (if the Company files the Initial Registration
Statement without affording the Holders the opportunity to review and comment on the same as required by Section 3(a) herein,
the Company shall be deemed to have not satisfied this clause (i)), or (ii) the Company fails to file with the Commission a request
for acceleration of a Registration Statement in accordance with Rule 461 promulgated by the Commission pursuant to the Securities
Act, within five Trading Days of the date that the Company is notified (orally or in writing, whichever is earlier) by the Commission
that such Registration Statement will not be “reviewed” or will not be subject to further review, or (iii) prior to
the effective date of a Registration Statement, the Company fails to file a pre-effective amendment and otherwise respond in writing
to comments made by the Commission in respect of such Registration Statement within ten (10) calendar days after the receipt of
comments by or notice from the Commission that such amendment is required in order for such Registration Statement to be declared
effective, or (iv) a Registration Statement registering for resale all of the Registrable Securities is not declared effective
by the Commission by the Effectiveness Date of the Initial Registration Statement, or (v) after the effective date of a Registration
Statement, such Registration Statement ceases for any reason to remain continuously effective as to all Registrable Securities
included in such Registration Statement, or the Holders are otherwise not permitted to utilize the Prospectus therein to resell
such Registrable Securities, for more than ten (10) consecutive calendar days or more than an aggregate of fifteen (15) calendar
days (which need not be consecutive calendar days) during any 12-month period (any such failure or breach being referred to as
an “Event”, and for purposes of clauses (i) and (iv), the date on which such Event occurs, and for purpose
of clause (ii) the date on which such five (5) Trading Day period is exceeded, and for purpose of clause (iii) the date which
such ten (10) calendar day period is exceeded, and for purpose of clause (v) the date on which such ten (10) or fifteen (15) calendar
day period, as applicable, is exceeded being referred to as “Event Date”), then, in addition to any other rights
the Holders may have hereunder or under applicable law, on each such Event Date and on each monthly anniversary of each such Event
Date (if the applicable Event shall not have been cured by such date) until the applicable Event is cured, the Company shall pay
to each Holder an amount in cash, as partial liquidated damages and not as a penalty, equal to 2.0% of the aggregate purchase
price paid by such Holder pursuant to the Purchase Agreement. If the Company fails to pay any partial liquidated damages pursuant
to this Section in full within seven days after the date payable, the Company will pay interest thereon at a rate of 18% per annum
(or such lesser maximum amount that is permitted to be paid by applicable law) to the Holder, accruing daily from the date such
partial liquidated damages are due until such amounts, plus all such interest thereon, are paid in full. The partial liquidated
damages pursuant to the terms hereof shall apply on a daily pro rata basis for any portion of a month prior to the cure of an
Event.

 

(e)          If
Form S-1 is not available for the registration of the resale of Registrable Securities hereunder, the Company shall (i) register
the resale of the Registrable Securities on Form S-1 and the Company shall maintain the effectiveness of the Registration Statement
then in effect until such time as a Registration Statement on Form S-1 covering the Registrable Securities has been declared effective
by the Commission.

 

		3.	Registration Procedures.

 

In
connection with the Company’s registration obligations hereunder, the Company shall:

 

    	6

    	 

    

 

(a)          Not
less than five (5) Trading Days prior to the filing of each Registration Statement and not less than one (1) Trading Day prior
to the filing of any related Prospectus or any amendment or supplement thereto (including any document that would be incorporated
or deemed to be incorporated therein by reference), the Company shall (i) furnish to each Holder copies of all such documents
proposed to be filed, which documents (other than those incorporated or deemed to be incorporated by reference) will be subject
to the review of such Holders, and (ii) cause its officers and directors, counsel and independent registered public accountants
to respond to such inquiries as shall be necessary, in the reasonable opinion of respective counsel to each Holder, to conduct
a reasonable investigation within the meaning of the Securities Act. Notwithstanding the above, the Company shall not be obligated
to provide the Holders advance copies of any other registration statement registering other securities in addition to those required
hereunder, or any Prospectus prepared thereto. The Company shall not file a Registration Statement or any such Prospectus or any
amendments or supplements thereto to which the Holders of a majority of the Registrable Securities shall reasonably object in
good faith, provided that, the Company is notified of such objection in writing no later than five (5) Trading Days after the
Holders have been so furnished copies of a Registration Statement or one (1) Trading Day after the Holders have been so furnished
copies of any related Prospectus or amendments or supplements thereto. Each Holder agrees to furnish to the Company a completed
questionnaire in the form attached to this Agreement as Annex B (a “Selling Stockholder Questionnaire”)
on a date that is not less than two (2) Trading Days prior to the Filing Date or by the end of the fourth (4th) Trading
Day following the date on which such Holder receives draft materials in accordance with this Section.

 

(b)          (i)
Prepare and file with the Commission such amendments, including post-effective amendments, to a Registration Statement and the
Prospectus used in connection therewith as may be necessary to keep a Registration Statement continuously effective as to the
applicable Registrable Securities for the Effectiveness Period and prepare and file with the Commission such additional Registration
Statements in order to register for resale under the Securities Act all of the Registrable Securities, (ii) cause the related
Prospectus to be amended or supplemented by any required Prospectus supplement (subject to the terms of this Agreement), and,
as so supplemented or amended, to be filed pursuant to Rule 424, (iii) respond as promptly as reasonably possible to any comments
received from the Commission with respect to a Registration Statement or any amendment thereto and provide as promptly as reasonably
possible to the Holders true and complete copies of all correspondence from and to the Commission relating to a Registration Statement
(provided that, the Company shall excise any information contained therein which would constitute material non-public information
regarding the Company or any of its Subsidiaries), and (iv) comply in all material respects with the applicable provisions of
the Securities Act and the Exchange Act with respect to the disposition of all Registrable Securities covered by a Registration
Statement during the applicable period in accordance (subject to the terms of this Agreement) with the intended methods of disposition
by the Holders thereof set forth in such Registration Statement as so amended or in such Prospectus as so supplemented.

 

    	7

    	 

    

 

(c)          If
during the Effectiveness Period, the number of Registrable Securities at any time exceeds 100% of the number of shares of Common
Stock then registered in a Registration Statement, then the Company shall file as soon as reasonably practicable, but in any case
prior to the applicable Filing Date, an additional Registration Statement covering the resale by the Holders of not less than
the number of such Registrable Securities.

 

(d)          Notify
the Holders of Registrable Securities to be sold (which notice shall, pursuant to clauses (iii) through (vi) hereof, be accompanied
by an instruction to suspend the use of the Prospectus until the requisite changes have been made) as promptly as reasonably possible
(and, in the case of (i)(A) below, not less than one (1) Trading Day prior to such filing) and (if requested by any such Person)
confirm such notice in writing no later than one (1) Trading Day following the day (i)(A) when a Prospectus or any Prospectus
supplement or post-effective amendment to a Registration Statement is proposed to be filed, (B) when the Commission notifies the
Company whether there will be a “review” of such Registration Statement and whenever the Commission comments in writing
on such Registration Statement, and (C) with respect to a Registration Statement or any post-effective amendment, when the same
has become effective, (ii) of any request by the Commission or any other federal or state governmental authority for amendments
or supplements to a Registration Statement or Prospectus or for additional information, (iii) of the issuance by the Commission
or any other federal or state governmental authority of any stop order suspending the effectiveness of a Registration Statement
covering any or all of the Registrable Securities or the initiation of any Proceedings for that purpose, (iv) of the receipt by
the Company of any notification with respect to the suspension of the qualification or exemption from qualification of any of
the Registrable Securities for sale in any jurisdiction, or the initiation or threatening of any Proceeding for such purpose,
(v) of the occurrence of any event or passage of time that makes the financial statements included in a Registration Statement
ineligible for inclusion therein or any statement made in a Registration Statement or Prospectus or any document incorporated
or deemed to be incorporated therein by reference untrue in any material respect or that requires any revisions to a Registration
Statement, Prospectus or other documents so that, in the case of a Registration Statement or the Prospectus, as the case may be,
it will not contain any untrue statement of a material fact or omit to state any 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, and (vi) of
the occurrence or existence of any pending corporate development with respect to the Company that the Company believes may be
material and that, in the determination of the Company, makes it not in the best interest of the Company to allow continued availability
of a Registration Statement or Prospectus, provided, however, in no event shall any such notice contain any information
which would constitute material, non-public information regarding the Company or any of its Subsidiaries.

 

    	8

    	 

    

 

(e)          Use
its best efforts to avoid the issuance of, or, if issued, obtain the withdrawal of (i) any order stopping or suspending the effectiveness
of a Registration Statement, or (ii) any suspension of the qualification (or exemption from qualification) of any of the Registrable
Securities for sale in any jurisdiction, at the earliest practicable moment.

 

(f)          Furnish
to each Holder, without charge, at least one conformed copy of each such Registration Statement and each amendment thereto, including
financial statements and schedules, all documents incorporated or deemed to be incorporated therein by reference to the extent
requested by such Person, and all non-confidential exhibits to the extent requested by such Person (including those previously
furnished or incorporated by reference) promptly after the filing of such documents with the Commission; provided, that any such
item which is available on the EDGAR system (or successor thereto) need not be furnished in physical form.

 

(g)          Subject
to the terms of this Agreement, the Company hereby consents to the use of such Prospectus and each amendment or supplement thereto
by each of the selling Holders in connection with the offering and sale of the Registrable Securities covered by such Prospectus
and any amendment or supplement thereto, except after the giving of any notice pursuant to Section 3(d).

 

(h)          
The Company shall cooperate with any broker-dealer through which a Holder proposes to resell its Registrable Securities in effecting
a filing with the FINRA Corporate Financing Department pursuant to FINRA Rule 5110, as requested by any such Holder, and the Company
shall pay the filing fee required by such filing within two (2) Business Days of request therefor.

 

(i)          Prior
to any resale of Registrable Securities by a Holder, use its commercially reasonable efforts to register or qualify or cooperate
with the selling Holders in connection with the registration or qualification (or exemption from the Registration or qualification)
of such Registrable Securities for the resale by the Holder under the securities or Blue Sky laws of such jurisdictions within
the United States as any Holder reasonably requests in writing, to keep each registration or qualification (or exemption therefrom)
effective during the Effectiveness Period and to do any and all other acts or things reasonably necessary to enable the disposition
in such jurisdictions of the Registrable Securities covered by each Registration Statement; provided, that, the Company shall
not be required to qualify generally to do business in any jurisdiction where it is not then so qualified, subject the Company
to any material tax in any such jurisdiction where it is not then so subject or file a general consent to service of process in
any such jurisdiction.

 

    	9

    	 

    

 

(j)          If
requested by a Holder, cooperate with such Holder to facilitate the timely preparation and delivery of certificates representing
Registrable Securities to be delivered to a transferee pursuant to a Registration Statement, which certificates shall be free,
to the extent permitted by the Purchase Agreement, of all restrictive legends, and to enable such Registrable Securities to be
in such denominations and registered in such names as any such Holder may request.

 

(k)          Upon
the occurrence of any event contemplated by Section 3(d), as promptly as reasonably possible under the circumstances taking into
account the Company’s good faith assessment of any adverse consequences to the Company and its stockholders of the premature
disclosure of such event, prepare a supplement or amendment, including a post-effective amendment, to a Registration Statement
or a supplement to the related Prospectus or any document incorporated or deemed to be incorporated therein by reference, and
file any other required document so that, as thereafter delivered, neither a Registration Statement nor such Prospectus will contain
an untrue statement of a material fact or omit to state 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.  If
the Company notifies the Holders in accordance with clauses (iii) through (vi) of Section 3(d) above to suspend the use of any
Prospectus until the requisite changes to such Prospectus have been made, then the Holders shall suspend use of such Prospectus.
The Company will use its best efforts to ensure that the use of the Prospectus may be resumed as promptly as is practicable. The
Company shall be entitled to exercise its right under this Section 3(k) to suspend the availability of a Registration Statement
and Prospectus, subject to the payment of partial liquidated damages otherwise required pursuant to Section 2(d), for a period
not to exceed 60 calendar days (which need not be consecutive days) in any 12-month period.

 

(l)           Comply
with all applicable rules and regulations of the Commission.

 

(m)         The
Company shall use its best efforts to maintain eligibility for use of Form S-1 (or any successor form thereto) for the registration
of the resale of Registrable Securities.

 

(n)          The
Company may require each selling Holder to furnish to the Company a certified statement as to the number of shares of Common Stock
beneficially owned by such Holder and, if required by the Commission, the natural persons thereof that have voting and dispositive
control over the shares. During any periods that the Company is unable to meet its obligations hereunder with respect to the registration
of the Registrable Securities solely because any Holder fails to furnish such information within three Trading Days of the Company’s
request, any liquidated damages that are accruing at such time as to such Holder only shall be tolled and any Event that may otherwise
occur solely because of such delay shall be suspended as to such Holder only, until such information is delivered to the Company.

 

    	10

    	 

    

 

4.
           Registration Expenses. All fees and expenses incident to the performance of or compliance with, this Agreement by the
Company shall be borne by the Company whether or not any Registrable Securities are sold pursuant to a Registration Statement.
The fees and expenses referred to in the foregoing sentence shall include, without limitation, (i) all registration and filing
fees (including, without limitation, fees and expenses of the Company’s counsel and independent registered public accountants)
(A) with respect to filings made with the Commission, (B) with respect to filings required to be made with any Trading Market
on which the Common Stock is then listed for trading, or (C) in compliance with applicable state securities or Blue Sky laws reasonably
agreed to by the Company in writing (including, without limitation, fees and disbursements of counsel for the Company in connection
with Blue Sky qualifications or exemptions of the Registrable Securities), (ii) printing expenses (including, without limitation,
expenses of printing certificates for Registrable Securities), (iii) messenger, telephone and delivery expenses, (iv) fees and
disbursements of counsel for the Company, (v) Securities Act liability insurance, if the Company so desires such insurance, and
(vi) fees and expenses of all other Persons retained by the Company in connection with the consummation of the transactions contemplated
by this Agreement. In addition, the Company shall be responsible for all of its internal expenses incurred in connection with
the consummation of the transactions contemplated by this Agreement (including, without limitation, all salaries and expenses
of its officers and employees performing legal or accounting duties), the expense of any annual audit and the fees and expenses
incurred in connection with the listing of the Registrable Securities on any securities exchange as required hereunder. In no
event shall the Company be responsible for any broker or similar commissions of any Holder or, except to the extent provided for
in the Transaction Documents, any legal fees or other costs of the Holders.

 

    	11

    	 

    
  

		5.	Indemnification.

 

(a)          Indemnification
by the Company. The Company shall, notwithstanding any termination of this Agreement, indemnify and hold harmless each Holder,
the officers, directors, members, partners, agents, brokers (including brokers who offer and sell Registrable Securities as principal
as a result of a pledge or any failure to perform under a margin call of Common Stock), investment advisors and employees (and
any other Persons with a functionally equivalent role of a Person holding such titles, notwithstanding a lack of such title or
any other title) of each of them, each Person who controls any such Holder (within the meaning of Section 15 of the Securities
Act or Section 20 of the Exchange Act) and the officers, directors, members, stockholders, partners, agents and employees (and
any other Persons with a functionally equivalent role of a Person holding such titles, notwithstanding a lack of such title or
any other title) of each such controlling Person, to the fullest extent permitted by applicable law, from and against any and
all losses, claims, damages, liabilities, costs (including, without limitation, reasonable attorneys’ fees) and expenses
(collectively, “Losses”), as incurred, arising out of or relating to (1) any untrue or alleged untrue statement
of a material fact contained in a Registration Statement, any Prospectus or any form of prospectus or in any amendment or supplement
thereto or in any preliminary prospectus, or arising out of or relating to any omission or alleged omission of a material fact
required to be stated therein or necessary to make the statements therein (in the case of any Prospectus or supplement thereto,
in light of the circumstances under which they were made) not misleading or (2) any violation or alleged violation by the Company
of the Securities Act, the Exchange Act or any state securities law, or any rule or regulation thereunder, in connection with
the performance of its obligations under this Agreement, except to the extent, but only to the extent, that (i) such untrue statements
or omissions are based solely upon information regarding such Holder furnished in writing to the Company by such Holder expressly
for use therein, or to the extent that such information relates to such Holder or such Holder’s proposed method of distribution
of Registrable Securities and was reviewed and expressly approved in writing by such Holder expressly for use in a Registration
Statement, such Prospectus or in any amendment or supplement thereto (it being understood that the Holder has approved Annex A
hereto for this purpose) or (ii) in the case of an occurrence of an event of the type specified in Section 3(d)(iii)-(vi), the
use by such Holder of an outdated, defective or otherwise unavailable Prospectus after the Company has notified such Holder in
writing that the Prospectus is outdated, defective or otherwise unavailable for use by such Holder and prior to the receipt by
such Holder of the Advice contemplated in Section 6(d), but only if and to the extent that following the receipt of the Advice
the misstatement or omission giving rise to such Loss would have been corrected. The Company shall notify the Holders promptly
of the institution, threat or assertion of any Proceeding arising from or in connection with the transactions contemplated by
this Agreement of which the Company is aware. Such indemnity shall remain in full force and effect regardless of any investigation
made by or on behalf of such indemnified person and shall survive the transfer of any Registrable Securities by any of the Holders
in accordance with Section 6(h).

 

    	12

    	 

    

 

(b)          Indemnification
by Holders. Each Holder shall, severally and not jointly, indemnify and hold harmless the Company, its directors, officers,
and employees, each Person who controls the Company (within the meaning of Section 15 of the Securities Act and Section 20 of
the Exchange Act), and the directors, officers or employees of such controlling Persons, to the fullest extent permitted by applicable
law, from and against all Losses, as incurred, to the extent arising out of or based solely upon: (x) such Holder’s failure
to comply with any applicable prospectus delivery requirements of the Securities Act through no fault of the Company or (y) any
untrue or alleged untrue statement of a material fact contained in any Registration Statement, any Prospectus, or in any amendment
or supplement thereto or in any preliminary prospectus, or arising out of or relating to any omission or alleged omission of a
material fact required to be stated therein or necessary to make the statements therein (in the case of any Prospectus or supplement
thereto, in light of the circumstances under which they were made) not misleading (i) to the extent, but only to the extent, that
such untrue statement or omission is contained in any information so furnished in writing by such Holder to the Company expressly
for inclusion in such Registration Statement or such Prospectus or (ii) to the extent, but only to the extent, that such information
relates to such Holder’s proposed method of distribution of Registrable Securities and was reviewed and expressly approved
in writing by such Holder expressly for use in a Registration Statement (it being understood that the Holder has approved Annex
A hereto for this purpose), such Prospectus or in any amendment or supplement thereto or (iii) in the case of an occurrence of
an event of the type specified in Section 3(d)(iii)-(vi), to the extent, but only to the extent, related to the use by such Holder
of an outdated, defective or otherwise unavailable Prospectus after the Company has notified such Holder in writing that the Prospectus
is outdated, defective or otherwise unavailable for use by such Holder and prior to the receipt by such Holder of the Advice contemplated
in Section 6(d), but only if and to the extent that following the receipt of the Advice the misstatement or omission giving rise
to such Loss would have been corrected. In no event shall the liability of any selling Holder under this Section 5(b) be greater
in amount than the dollar amount of the net proceeds received by such Holder upon the sale of the Registrable Securities giving
rise to such indemnification obligation.

 

(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 have the right to 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; provided, that, the failure of any Indemnified Party to give such notice
shall not relieve the Indemnifying Party of its obligations or liabilities pursuant to this Agreement, except (and only) to the
extent that it shall be finally determined by a court of competent jurisdiction (which determination is not subject to appeal
or further review) that such failure shall have materially and adversely prejudiced the Indemnifying Party.

 

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 unless: (1) the Indemnifying
Party has agreed in writing to pay such fees and expenses, (2) the Indemnifying Party shall have failed promptly to assume the
defense of such Proceeding and to employ counsel reasonably satisfactory to such Indemnified Party in any such Proceeding, or
(3) the named parties to any such Proceeding (including any impleaded parties) include both such Indemnified Party and the Indemnifying
Party, and counsel to the Indemnified Party shall reasonably believe that a material conflict of interest is likely to exist if
the same counsel were to represent such Indemnified Party and the Indemnifying Party (in which case, if such Indemnified Party
notifies the Indemnifying Party in writing that it elects to employ separate counsel at the expense of the Indemnifying Party,
the Indemnifying Party shall not have the right to assume the defense thereof and the reasonable fees and expenses of no more
than one separate counsel shall be at the expense of the Indemnifying Party). The Indemnifying Party shall not be liable for any
settlement of any such Proceeding effected without its written consent, which consent shall not be unreasonably withheld or delayed.
No Indemnifying Party shall, without the prior written consent of the Indemnified Party, effect any settlement of any pending
Proceeding in respect of which any Indemnified Party is a party, unless such settlement includes an unconditional release of such
Indemnified Party from all liability on claims that are the subject matter of such Proceeding.

 

    	13

    	 

    

 

Subject
to the terms of this Agreement, 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 Trading Days of written notice thereof to the Indemnifying
Party; provided, that, the Indemnified Party shall promptly reimburse the Indemnifying Party for that portion of such fees and
expenses applicable to such actions for which such Indemnified Party is finally determined by a court of competent jurisdiction
(which determination is not subject to appeal or further review) not to be entitled to indemnification hereunder.

 

(d)          Contribution.
If the indemnification under Section 5(a) or 5(b) is unavailable to an Indemnified Party or insufficient to hold an Indemnified
Party harmless for any Losses, then each Indemnifying Party shall contribute to the amount paid or payable by such Indemnified
Party, 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 relates 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 this Agreement, any reasonable attorneys’ or other 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 Section was available to such party in accordance with its terms.

 

    	14

    	 

    

 

The
parties hereto agree that it would not be just and equitable if contribution pursuant to this Section 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 provisions of this Section 5(d), no Holder shall be required to
contribute pursuant to this Section 5(d), in the aggregate, any amount in excess of the amount by which the net proceeds actually
received by such Holder from the sale of the Registrable Securities subject to the Proceeding exceeds the amount of any damages
that such Holder has otherwise been required to pay by reason of such untrue or alleged untrue statement or omission or alleged
omission.

 

The
indemnity and contribution agreements contained in this Section are in addition to any liability that the Indemnifying Parties
may have to the Indemnified Parties.

 

		6.	Miscellaneous.

 

(a)          Remedies.
In the event of a breach by the Company or by a Holder of any of their respective obligations under this Agreement, each Holder
or the Company, as the case may be, in addition to being entitled to exercise all rights granted by law and under this Agreement,
including recovery of damages, shall be entitled to specific performance of its rights under this Agreement. Each of the Company
and each Holder agrees that monetary damages would not provide adequate compensation for any losses incurred by reason of a breach
by it of any of the provisions of this Agreement and hereby further agrees that, in the event of any action for specific performance
in respect of such breach, it shall not assert or shall waive the defense that a remedy at law would be adequate.

 

(b)          No
Piggyback on Registrations; Prohibition on Filing Other Registration Statements. Neither the Company nor any of its security
holders (other than the Holders in such capacity pursuant hereto) may include securities of the Company in any Registration Statements
other than the Registrable Securities. The Company shall not file any other registration statements until all Registrable Securities
are registered pursuant to a Registration Statement that is declared effective by the Commission, provided that this Section 6(b)
shall not prohibit the Company from filing amendments to registration statements filed prior to the date of this Agreement.

 

(c)          Compliance.
Each Holder covenants and agrees that it will comply with the prospectus delivery requirements of the Securities Act as applicable
to it (unless an exemption therefrom is available) in connection with sales of Registrable Securities pursuant to a Registration
Statement.

 

(d)          Discontinued
Disposition. By its acquisition of Registrable Securities, each Holder agrees that, upon receipt of a notice from the Company
of the occurrence of any event of the kind described in Section 3(d)(iii) through (vi), such Holder will forthwith discontinue
disposition of such Registrable Securities under a Registration Statement until it is advised in writing (the “Advice”)
by the Company that the use of the applicable Prospectus (as it may have been supplemented or amended) may be resumed. The Company
will use its best efforts to ensure that the use of the Prospectus may be resumed as promptly as is practicable. The Company agrees
and acknowledges that any periods during which the Holder is required to discontinue the disposition of the Registrable Securities
hereunder shall be subject to the provisions of Section 2(d).

 

    	15

    	 

    

 

(e)          Piggy-Back
Registrations. If, at any time during the Effectiveness Period, there is not an effective Registration Statement covering
all of the Registrable Securities and the Company shall determine to prepare and file with the Commission a registration statement
relating to an offering for its own account or the account of others under the Securities Act of any of its equity securities,
other than on Form S-4 or Form S-8 (each as promulgated under the Securities Act) or their then equivalents relating to equity
securities to be issued solely in connection with any acquisition of any entity or business or equity securities issuable in connection
with the Company’s stock option or other employee benefit plans, then the Company shall deliver to each Holder a written
notice of such determination and, if within fifteen days after the date of the delivery of such notice, any such Holder shall
so request in writing, the Company shall include in such registration statement all or any part of such Registrable Securities
such Holder requests to be registered that are not otherwise included in an effective Registration Statement; provided,
however, that the Company shall not be required to register any Registrable Securities pursuant to this Section 6(e) that
are eligible for resale pursuant to Rule 144 (without volume restrictions or current public information requirements) promulgated
by the Commission pursuant to the Securities Act or that are the subject of a then effective Registration Statement.

 

(f)          Amendments
and Waivers. The provisions of this Agreement, including the provisions of this sentence, may not be amended, modified or
supplemented, and waivers or consents to departures from the provisions hereof may not be given, unless the same shall be in writing
and signed by the Company and the Holders of 67% or more of the then outstanding Registrable Securities (for purposes of clarification,
this includes any Registrable Securities issuable upon exercise or conversion of any Security). If a Registration Statement does
not register all of the Registrable Securities pursuant to a waiver or amendment done in compliance with the previous sentence,
then the number of Registrable Securities to be registered for each Holder shall be reduced pro rata among all Holders and each
Holder shall have the right to designate which of its Registrable Securities shall be omitted from such Registration Statement.
Notwithstanding the foregoing, a waiver or consent to depart from the provisions hereof with respect to a matter that relates
exclusively to the rights of a Holder or some Holders and that does not directly or indirectly affect the rights of other Holders
may be given only by such Holder or Holders of all of the Registrable Securities to which such waiver or consent relates; provided,
however, that the provisions of this sentence may not be amended, modified, or supplemented except in accordance with the
provisions of the first sentence of this Section 6(f). No consideration shall be offered or paid to any Person to amend or consent
to a waiver or modification of any provision of this Agreement unless the same consideration also is offered to all of the parties
to this Agreement.

 

(g)          Notices.
Any and all notices or other communications or deliveries required or permitted to be provided hereunder shall be delivered as
set forth in the Purchase Agreement.

 

    	16

    	 

    

 

(h)          Successors
and Assigns. This Agreement shall inure to the benefit of and be binding upon the successors and permitted assigns of each
of the parties and shall inure to the benefit of each Holder. The Company may not assign (except by merger) its rights or obligations
hereunder without the prior written consent of all of the Holders of the then outstanding Registrable Securities. Each Holder
may assign their respective rights hereunder in the manner and to the Persons as permitted under Section 5.7 of the Purchase Agreement.

 

(i)           No
Inconsistent Agreements. Neither the Company nor any of its Subsidiaries has entered, as of the date hereof, nor shall the
Company or any of its Subsidiaries, on or after the date of this Agreement, enter into any agreement with respect to its securities,
that would have the effect of impairing the rights granted to the Holders in this Agreement or otherwise conflicts with the provisions
hereof. Except as set forth on Schedule 6(i), neither the Company nor any of its Subsidiaries has previously entered into
any agreement granting any registration rights with respect to any of its securities to any Person that have not been satisfied
in full.

 

(j)           Execution
and Counterparts. This Agreement may be executed in two or more counterparts, all of which when taken together 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, it being understood that both parties need not sign the same counterpart. In the event that any signature is delivered
by facsimile transmission or by e-mail delivery of a “.pdf” format data file, such signature shall create a valid
and binding obligation of the party executing (or on whose behalf such signature is executed) with the same force and effect as
if such facsimile or “.pdf” signature page were an original thereof.

 

(k)           Governing
Law. All questions concerning the construction, validity, enforcement and interpretation of this Agreement shall be determined
in accordance with the provisions of the Purchase Agreement.

 

(l)           Cumulative
Remedies. The remedies provided herein are cumulative and not exclusive of any other remedies provided by law.

 

(m)          Severability.
If any term, provision, covenant or restriction of this Agreement is held by a court of competent jurisdiction to be invalid,
illegal, void or unenforceable, the remainder of the terms, provisions, covenants and restrictions set forth herein shall remain
in full force and effect and shall in no way be affected, impaired or invalidated, and the parties hereto shall use their commercially
reasonable efforts to find and employ an alternative means to achieve the same or substantially the same result as that contemplated
by such term, provision, covenant or restriction. It is hereby stipulated and declared to be the intention of the parties that
they would have executed the remaining terms, provisions, covenants and restrictions without including any of such that may be
hereafter declared invalid, illegal, void or unenforceable.

 

    	17

    	 

    

 

(n)          Headings.
The headings in this Agreement are for convenience only, do not constitute a part of the Agreement and shall not be deemed to
limit or affect any of the provisions hereof.

 

(o)          Independent
Nature of Holders’ Obligations and Rights. The obligations of each Holder hereunder are several and not joint with the
obligations of any other Holder hereunder, and no Holder shall be responsible in any way for the performance of the obligations
of any other Holder hereunder. Nothing contained herein or in any other agreement or document delivered at any closing, and no
action taken by any Holder pursuant hereto or thereto, shall be deemed to constitute the Holders as a partnership, an association,
a joint venture or any other kind of group or entity, or create a presumption that the Holders are in any way acting in concert
or as a group or entity with respect to such obligations or the transactions contemplated by this Agreement or any other matters,
and the Company acknowledges that the Holders are not acting in concert or as a group, and the Company shall not asset any such
claim, with respect to such obligations or transactions. Each Holder shall be entitled to protect and enforce its rights, including
without limitation the rights arising out of this Agreement, and it shall not be necessary for any other Holder to be joined as
an additional party in any proceeding for such purpose. The use of a single agreement with respect to the obligations of the Company
contained was solely in the control of the Company, not the action or decision of any Holder, and was done solely for the convenience
of the Company and not because it was required or requested to do so by any Holder. It is expressly understood and agreed that
each provision contained in this Agreement is between the Company and a Holder, solely, and not between the Company and the Holders
collectively and not between and among Holders.

 

********************

 

(Signature
Pages Follow)

 

    	18

    	 

    

 

IN
WITNESS WHEREOF, the parties have executed this Registration Rights Agreement as of the date first written above.

 

	 	22nd
    century group, inc.
	 	 	 
	 	By: 	/s/ Joseph Pandolfino
	 	 	Name:  Joseph Pandolfino
	 	 	Title: Chief Executive Officer

 

[SIGNATURE PAGE
OF HOLDERS FOLLOWS]

 

    	 

    	 

    

 

[SIGNATURE
PAGE OF HOLDERS TO XXII RRA]

 

Name of Holder: Sabby Healthcare
Volatility Master Fund, Ltd.

 

Signature of Authorized Signatory
of Holder: /s/ Robert Grundstein

 

Name of Authorized Signatory: Robert
Grundstein

 

Title of Authorized Signatory: COO
of Holder’s Investment Manager

 

Name of Holder: Sabby Volatility
Warrant Master Fund, Ltd.

 

Signature of Authorized Signatory
of Holder: /s/ Robert Grundstein

 

Name of Authorized Signatory: Robert
Grundstein

 

Title of Authorized Signatory: COO
of Holder’s Investment Manager

 

    	 

    	 

    

 

Annex A

 

Plan of Distribution

 

Each
Selling Stockholder (the “Selling Stockholders”) of the securities and any of their pledgees, assignees and
successors-in-interest may, from time to time, sell any or all of their securities covered hereby on the OTC Bulletin Board or
any other stock exchange, market or trading facility on which the securities are traded or in private transactions. These sales
may be at fixed or negotiated prices. A Selling Stockholder may use any one or more of the following methods when selling securities:

 

		·	ordinary
                                                                                                               brokerage transactions
                                                                                                               and transactions
                                                                                                               in which the broker-dealer
                                                                                                               solicits purchasers;

 

		·	block
                                                                                                               trades in which
                                                                                                               the broker-dealer
                                                                                                               will attempt to
                                                                                                               sell the securities
                                                                                                               as agent but may
                                                                                                               position and resell
                                                                                                               a portion of the
                                                                                                               block as principal
                                                                                                               to facilitate the
                                                                                                               transaction;

 

		·	purchases
                                                                                                               by a broker-dealer
                                                                                                               as principal and
                                                                                                               resale by the broker-dealer
                                                                                                               for its account;

 

		·	an
                                                                                                               exchange distribution
                                                                                                               in accordance with
                                                                                                               the rules of the
                                                                                                               applicable exchange;

 

		·	privately
                                                                                                               negotiated transactions;

 

		·	settlement
                                                                                                               of short sales
                                                                                                               entered into after
                                                                                                               the effective date
                                                                                                               of the registration
                                                                                                               statement of which
                                                                                                               this prospectus
                                                                                                               is a part;

 

		·	in
                                                                                                               transactions through
                                                                                                               broker-dealers
                                                                                                               that agree with
                                                                                                               the Selling Stockholders
                                                                                                               to sell a specified
                                                                                                               number of such
                                                                                                               securities at a
                                                                                                               stipulated price
                                                                                                               per security;

 

		·	through
                                                                                                               the writing or
                                                                                                               settlement of options
                                                                                                               or other hedging
                                                                                                               transactions, whether
                                                                                                               through an options
                                                                                                               exchange or otherwise;

 

		·	a
                                                                                                               combination of
                                                                                                               any such methods
                                                                                                               of sale; or

 

		·	any
                                                                                                               other method permitted
                                                                                                               pursuant to applicable
                                                                                                               law.

 

The
Selling Stockholders may also sell securities under Rule 144 under the Securities Act of 1933, as amended (the “Securities
Act”), if available, rather than under this prospectus.

 

    	 

    	 

    

 

 

Broker-dealers
engaged by the Selling Stockholders may arrange for other brokers-dealers to participate in sales. Broker-dealers may receive
commissions or discounts from the Selling Stockholders (or, if any broker-dealer acts as agent for the purchaser of securities,
from the purchaser) in amounts to be negotiated, but, except as set forth in a supplement to this Prospectus, in the case of an
agency transaction not in excess of a customary brokerage commission in compliance with FINRA Rule 2440; and in the case of a
principal transaction a markup or markdown in compliance with FINRA IM-2440.

 

In
connection with the sale of the securities or interests therein, the Selling Stockholders may enter into hedging transactions
with broker-dealers or other financial institutions, which may in turn engage in short sales of the securities in the course of
hedging the positions they assume. The Selling Stockholders may also sell securities short and deliver these securities to close
out their short positions, or loan or pledge the securities to broker-dealers that in turn may sell these securities. The Selling
Stockholders may also enter into option or other transactions with broker-dealers or other financial institutions or create one
or more derivative securities which require the delivery to such broker-dealer or other financial institution of securities offered
by this prospectus, which securities such broker-dealer or other financial institution may resell pursuant to this prospectus
(as supplemented or amended to reflect such transaction).

 

The
Selling Stockholders and any broker-dealers or agents that are involved in selling the securities may be deemed to be “underwriters”
within the meaning of the Securities Act in connection with such sales. In such event, any commissions received by such broker-dealers
or agents and any profit on the resale of the securities purchased by them may be deemed to be underwriting commissions or discounts
under the Securities Act. Each Selling Stockholder has informed the Company that it does not have any written or oral agreement
or understanding, directly or indirectly, with any person to distribute the securities. In no event shall any broker-dealer receive
fees, commissions and markups which, in the aggregate, would exceed eight percent (8%).

 

The
Company is required to pay certain fees and expenses incurred by the Company incident to the registration of the securities. The
Company has agreed to indemnify the Selling Stockholders against certain losses, claims, damages and liabilities, including liabilities
under the Securities Act.

 

Because
Selling Stockholders may be deemed to be “underwriters” within the meaning of the Securities Act, they will be subject
to the prospectus delivery requirements of the Securities Act including Rule 172 thereunder. In addition, any securities covered
by this prospectus which qualify for sale pursuant to Rule 144 under the Securities Act may be sold under Rule 144 rather than
under this prospectus. The Selling Stockholders have advised us that there is no underwriter or coordinating broker acting in
connection with the proposed sale of the resale securities by the Selling Stockholders.

 

    	2

    	 

    

 

 

We
agreed to keep this prospectus effective until the earlier of (i) the date on which the securities may be resold by the Selling
Stockholders without registration and without regard to any volume or manner-of-sale limitations by reason of Rule 144, without
the requirement for the Company to be in compliance with the current public information under Rule 144 under the Securities Act
or any other rule of similar effect or (ii) all of the securities have been sold pursuant to this prospectus or Rule 144 under
the Securities Act or any other rule of similar effect. The resale securities will be sold only through registered or licensed
brokers or dealers if required under applicable state securities laws. In addition, in certain states, the resale securities covered
hereby may not be sold unless they have been registered or qualified for sale in the applicable state or an exemption from the
registration or qualification requirement is available and is complied with.

 

Under
applicable rules and regulations under the Exchange Act, any person engaged in the distribution of the resale securities may not
simultaneously engage in market making activities with respect to the common stock for the applicable restricted period, as defined
in Regulation M, prior to the commencement of the distribution. In addition, the Selling Stockholders will be subject to applicable
provisions of the Exchange Act and the rules and regulations thereunder, including Regulation M, which may limit the timing of
purchases and sales of securities of the common stock by the Selling Stockholders or any other person. We will make copies of
this prospectus available to the Selling Stockholders and have informed them of the need to deliver a copy of this prospectus
to each purchaser at or prior to the time of the sale (including by compliance with Rule 172 under the Securities Act).

 

    	3

    	 

    

 

 

Annex
B

 

22nd
Century group, inc.

 

Selling
Stockholder Notice and Questionnaire

 

The
undersigned beneficial owner of common stock (the “Registrable Securities”) of 22nd Century Group,
Inc., a Nevada corporation (the “Company”), understands that the Company has filed or intends to file with
the Securities and Exchange Commission (the “Commission”) a registration statement (the “Registration
Statement”) for the registration and resale under Rule 415 of the Securities Act of 1933, as amended (the “Securities
Act”), of the Registrable Securities, in accordance with the terms of the Registration Rights Agreement (the “Registration
Rights Agreement”) to which this document is annexed. A copy of the Registration Rights Agreement is available from
the Company upon request at the address set forth below. All capitalized terms not otherwise defined herein shall have the meanings
ascribed thereto in the Registration Rights Agreement.

 

Certain
legal consequences arise from being named as a selling stockholder in the Registration Statement and the related prospectus. Accordingly,
holders and beneficial owners of Registrable Securities are advised to consult their own securities law counsel regarding the
consequences of being named or not being named as a selling stockholder in the Registration Statement and the related prospectus.

 

NOTICE

 

The
undersigned beneficial owner (the “Selling Stockholder”) of Registrable Securities hereby elects to include
the Registrable Securities owned by it in the Registration Statement.

 

    	 

    	 

    

 

 

The undersigned
hereby provides the following information to the Company and represents and warrants that such information is accurate:

 

QUESTIONNAIRE

 

		1.	Name.

 

		(a)	Full Legal Name of Selling
Stockholder

 

	 

 

		(b)	Full Legal Name of Registered
Holder (if not the same as (a) above) through which Registrable Securities are held:

 

	 

 

		(c)	Full Legal Name of Natural
Control Person (which means a natural person who directly or indirectly alone or with others has power to vote or dispose of the
securities covered by this Questionnaire):

 

	 

  

2.
Address for Notices to Selling Stockholder:

 

	 
	 
	 

	Telephone: 	 

	Fax: 	 

	Contact Person: 	 

 

3.
Broker-Dealer Status:

 

		(a)	Are you a broker-dealer?

 

Yes
 ̈            No  ̈

 

		(b)	If “yes” to Section
3(a), did you receive your Registrable Securities as compensation for investment banking services to the Company?

 

Yes
 ̈            No  ̈

 

		Note:	If “no” to Section
3(b), the Commission’s staff has indicated that you should be identified as an underwriter in the Registration Statement.

 

    	2

    	 

    

 

		(c)	Are you an affiliate of a
broker-dealer?

 

Yes
 ̈            No  ̈

 

		(d)	If you are an affiliate of
a broker-dealer, do you certify that you purchased the Registrable Securities in the ordinary course of business, and at the time
of the purchase of the Registrable Securities to be resold, you had no agreements or understandings, directly or indirectly, with
any person to distribute the Registrable Securities?

 

Yes
 ̈            No  ̈

 

		Note:	If “no” to Section
3(d), the Commission’s staff has indicated that you should be identified as an underwriter in the Registration Statement.

 

4.
Beneficial Ownership of Securities of the Company Owned by the Selling Stockholder.

 

Except
as set forth below in this Item 4, the undersigned is not the beneficial or registered owner of any securities of the Company
other than the securities issuable pursuant to the Purchase Agreement.

 

		(a)	Type and Amount of other securities
beneficially owned by the Selling Stockholder:

 

	 
	 

  

    	3

    	 

    

  

5.
Relationships with the Company:

 

Except
as set forth below, neither the undersigned nor any of its affiliates, officers, directors or principal equity holders (owners
of 5% of more of the equity securities of the undersigned) 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:

 

	 
	 

  

The
undersigned agrees to promptly notify the Company of any inaccuracies or changes in the information provided herein that may occur
subsequent to the date hereof at any time while the Registration Statement remains effective.

 

By
signing below, the undersigned consents to the disclosure of the information contained herein in its answers to Items 1 through
5 and the inclusion of such information in the Registration Statement and the related prospectus and any amendments or
supplements thereto. 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 and any amendments
or supplements thereto.

 

IN
WITNESS WHEREOF the undersigned, by authority duly given, has caused this Notice and Questionnaire to be executed and delivered
either in person or by its duly authorized agent.

 

	Date: 	 	 	Beneficial Owner: 	 
	 	 	 	 	 
	 	 	 	By: 	 
	 	 	 	 	Name:
	 	 	 	 	Title:

 

PLEASE FAX A COPY (OR EMAIL A
..PDF COPY) OF THE COMPLETED AND EXECUTED NOTICE AND QUESTIONNAIRE, AND RETURN THE ORIGINAL BY OVERNIGHT MAIL, TO:

 

    	4FORM OF LOCK-UP AGREEMENT

 

January 6, 2013

 

Each Purchaser referenced below:

 

		Re:	Securities Purchase Agreement, dated as of January __, 2013 (the “Purchase Agreement”),
between 22nd Century Group, Inc., a Nevada corporation (the “Company”) and the purchasers signatory thereto
(each, a “Purchaser” and, collectively, the “Purchasers”).

 

Ladies and Gentlemen:

 

This letter
agreement (the “Letter Agreement”) is entered into pursuant to Section 2.2 of the Purchase Agreement and in
satisfaction of a condition of the Company’s obligations under the Purchase Agreement. The undersigned irrevocably agrees
with the Company that, from the date hereof until the 2-month anniversary of the date a registration statement registering 200%
of the shares of the Company’s common stock (“Common Stock”) underlying the Series __ Convertible Preferred
Stock and Common Stock Purchase Warrants issued pursuant to the Purchase Agreement has been declared effective by the Securities
and Exchange Commission (the “Commission” and such period, the “Restriction Period”), except
as provided for below, the undersigned will not offer, sell, contract to sell, hypothecate, pledge, short or hedge against or otherwise
dispose of (or enter into any transaction which is designed to, or might reasonably be expected to, result in the disposition (whether
by actual disposition or effective economic disposition due to cash settlement or otherwise) by the undersigned or any affiliate
of the undersigned or any person in privity with the undersigned or any affiliate of the undersigned), directly or indirectly,
including the filing (or participation in the filing) of a registration statement with the Commission in respect of, or establish
or increase a put equivalent position or liquidate or decrease a call equivalent position within the meaning of Section 16 of the
Securities Exchange Act of 1934, as amended (“Exchange Act”) with respect to, any shares of Common Stock and/or
any Common Stock Equivalents (as defined below) beneficially owned, held or hereafter acquired by the undersigned (collectively,
the “Securities”); provided, however, during the Restriction Period, the undersigned shall be
permitted to sell up to 5,000 shares of Common Stock per Trading Day in ordinary brokerage transactions provided that the aggregate
amount of shares of Common Stock sold during the Restriction Period does not exceed 50,000 shares of Common Stock (all share amounts
subject to adjustment for reverse and forward stock splits and the like).

 

“Common
Stock Equivalents” means any securities of the Company or its subsidiaries which would entitle the holder thereof to
acquire at any time Common Stock, including, without limitation, any debt, preferred stock, right, option, warrant or other instrument
that is at any time convertible into or exercisable or exchangeable for, or otherwise entitles the holder thereof to receive, Common
Stock. Beneficial ownership shall be calculated in accordance with Section 13(d) of the Exchange Act. Additionally, during the
Restriction Period, the undersigned shall not exercise or exchange for other securities (for cash or otherwise) any Common Stock
options or warrants of the Company. The Company will issue stop transfer instructions to its transfer agent in which the Company
instructs its transfer agent to not effectuate transfers of securities that are the subject of this Letter Agreement.

 

    	 

    	 

    

 

The undersigned
acknowledges that the execution, delivery and performance of this Letter Agreement is a material inducement to each Purchaser to
complete the transactions contemplated by the Purchase Agreement and that each Purchaser (which shall be a third party beneficiary
of this Letter Agreement) and the Company shall be entitled to specific performance of the undersigned’s obligations hereunder.
The undersigned hereby represents that the undersigned has the power and authority to execute, deliver and perform this Letter
Agreement, that the undersigned has received adequate consideration therefor and that the undersigned will indirectly benefit from
the closing of the transactions contemplated by the Purchase Agreement.

 

This Letter Agreement
may not be amended or otherwise modified in any respect without the written consent of each of the Company, each Purchaser and
the undersigned. This Letter Agreement shall be construed and enforced in accordance with the laws of the State of New York without
regard to the principles of conflict of laws. The undersigned hereby irrevocably submits to the exclusive
jurisdiction of the United States District Court sitting in the Southern District of New York and the courts of the State of New
York located in Manhattan, for the purposes of any suit, action or proceeding arising out of or relating to this Letter Agreement,
and hereby waives, and agrees not to assert in any such suit, action or proceeding, any claim that (i) it is not personally subject
to the jurisdiction of such court, (ii) the suit, action or proceeding is brought in an inconvenient forum, or (iii) the venue
of the suit, action or proceeding is improper. The undersigned hereby irrevocably waives personal service of process and
consents to process being served in any such suit, action or proceeding by receiving a copy thereof sent to the Company at the
address in effect for notices to it under the Purchase Agreement and agrees that such service shall constitute good and sufficient
service of process and notice thereof. The undersigned hereby waives any right to a trial by jury.

 

Nothing contained herein
shall be deemed to limit in any way any right to serve process in any manner permitted by law. The undersigned agrees and understands
that this Letter Agreement does not intend to create any relationship between the undersigned and each Purchaser and that each
Purchaser is not entitled to cast any votes on the matters herein contemplated and that no issuance or sale of the Securities is
created or intended by virtue of this Letter Agreement.

 

This Letter Agreement
shall be binding on successors and assigns of the undersigned with respect to the Securities and any such successor or assign shall
enter into a similar agreement for the benefit of the Purchasers.

 

*** SIGNATURE PAGE FOLLOWS***

 

    	2

    	 

    

 

This Letter Agreement
may be executed in two or more counterparts, all of which when taken together may be considered one and the same agreement.

 

	 	 
	Signature	 
	 	 
	Print Name	 
	 	 
	Position in Company (if applicable)	 
	 	 
	Address for Notice:	 
	 	 
	 	 
	 	 
	 	 
	 	 
	 	 
	Number of shares of Common Stock	 
	 	 
	 	 

 

Number of shares of Common Stock underlying
subject to warrants, options, debentures or other convertible securities

 

By signing below, the
Company agrees to enforce the restrictions on transfer set forth in this Letter Agreement.

 

22nd Century Group, Inc.

 

	By:	 	 

	Name:	Henry Sicignano III	 
	Title:	President	 

 

    	3

Source: [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00211-of-00352.parquet"}, [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00211-of-00352.parquet"}]]