FORM 4
[ ] Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).         
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES
                                                                                  
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Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 or Section 30(h) of the Investment Company Act of 1940
                      

1. Name and Address of Reporting Person *

JAMES THOMAS L.
2. Issuer Name and Ticker or Trading Symbol

22nd Century Group, Inc. [ XXII ]
5. Relationship of Reporting Person(s) to Issuer (Check all applicable)

_____ Director                      _____ 10% Owner
__ X __ Officer (give title below)      _____ Other (specify below)
VP, General Counsel & Sec'y.
(Last)          (First)          (Middle)

C/O 22ND CENTURY GROUP, INC., 9530 MAIN STREET
3. Date of Earliest Transaction (MM/DD/YYYY)

5/27/2014
(Street)

CLARENCE, NY 14031
(City)        (State)        (Zip)
4. If Amendment, Date Original Filed (MM/DD/YYYY)

 
6. Individual or Joint/Group Filing (Check Applicable Line)

_ X _ Form filed by One Reporting Person
___ Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3)
2. Trans. Date 2A. Deemed Execution Date, if any 3. Trans. Code
(Instr. 8)
4. Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
5. Amount of Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 3 and 4)
6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V Amount (A) or (D) Price
Common Stock   5/27/2014     A    100000   A   (1) 100000   D    

Table II - Derivative Securities Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities)
1. Title of Derivate Security
(Instr. 3)
2. Conversion or Exercise Price of Derivative Security 3. Trans. Date 3A. Deemed Execution Date, if any 4. Trans. Code
(Instr. 8)
5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
6. Date Exercisable and Expiration Date 7. Title and Amount of Securities Underlying Derivative Security
(Instr. 3 and 4)
8. Price of Derivative Security
(Instr. 5)
9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares
Options to Purchase Common Stock   $2.61   5/27/2014     A      300000         (2) 5/27/2024   Common Stock   300000   $0   300000   D    

Explanation of Responses:
( 1)  Restricted shares awarded to the reporting person pursuant to the issuer's 2014 Omnibus Incentive Plan, which shares are subject to forfeiture until May 1, 2017, subject to certain exceptions.
( 2)  Fifty thousand (50,000) of the options vest immediately and the remaining options vest as follows: one hundred thousand (100,000) on each of May 1, 2015 and May 1, 2016, and fifty thousand (50,000) on May 1, 2017.

Reporting Owners
Reporting Owner Name / Address
Relationships
Director 10% Owner Officer Other
JAMES THOMAS L.
C/O 22ND CENTURY GROUP, INC.
9530 MAIN STREET
CLARENCE, NY 14031


VP, General Counsel & Sec'y.

Signatures
/s/ John J. Wolfel, Attorney-in-Fact for Thomas L. James 5/27/2014
** Signature of Reporting Person Date


Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4(b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB control number.
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