22nd Century Group, Inc. — Director's Dealing 2011

Jun 8, 2011

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: 22nd Century Group, Inc. (XXII.OB)
CIK: 0001347858
Period of Report: 2011-04-01

Reporting Person: SICIGNANO HENRY III (Director, President, Secretary)

Non-Derivative Transactions

Date	Security	Code	Shares	Price	A/D	Holdings After	Ownership
2011-04-01	Common Stock	A	600000	—	Acquired	822603	Direct
2011-04-04	Common Stock	P	1500	$1.20	Acquired	1500	Indirect
2011-04-11	Common Stock	P	5000	$1.25	Acquired	5000	Indirect
2011-05-03	Common Stock	P	3000	$1.25	Acquired	4500	Indirect
2011-05-26	Common Stock	P	1000	$1.15	Acquired	5500	Indirect
2011-05-31	Common Stock	P	2000	$1.22	Acquired	7500	Indirect
2011-06-07	Common Stock	P	110000	$1.03	Acquired	932603	Direct

Holdings (Non-Derivative)

Security	Shares	Ownership
Common Stock	2542347	Indirect

Holdings (Derivative)

Security	Exercise Price	Expiration	Underlying	Shares	Ownership
Warrant	$3.00	2016-01-25	Common Stock (69564)	69564	Direct
Warrant	$1.5	2016-01-25	Common Stock (15813)	15813	Indirect
Warrant	$3.00	2016-01-25	Common Stock (784600)	784600	Indirect

Footnotes

F1: Restricted stock granted April 1, 2011 to the reporting person under the 22nd Century Group, Inc. 2010 Equity Incentive Plan. The restricted stock vests and becomes exercisable to the extent of 25% on each of the first four anniversaries of the date of grant. The reporting person has filed with the IRS an 83(b) election in connection with this grant. Does not include the contingent right of the reporting person to receive up to 100,000 additional performance shares under the issuer's 2010 Equity Incentive Plan based on the achievement of certain performance targets.

F2: The shares acquired are subject to a lock-up agreement and were sold pursuant to the permitted exceptions.

F3: Represents 2,542,347 shares of 22nd Century Group, Inc. which are owned directly by Henry Sicignano III Group, LLC, of which Mr. Sicignano is the Manager.

F4: Represents warrants to purchase 15,813 shares of Common Stock and 784,600 shares of Common Stock, respectively, of 22nd Century Group, Inc., which were issued to Henry Sicignano III Group, LLC, of which Mr. Sicignano is the Manager.