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        22nd Century Group, Inc.

March 8, 2013

VIA EDGAR

        United States Securities and Exchange Commission

        Division of Corporation Finance

        100 F Street NE

        Washington, DC 20549

        Attn: Max A. Webb

 Re: 22nd Century Group, Inc.

Registration Statement on Form S-1

Filed February 4, 2013

File No.: 333-186449

Dear Mr. Webb:

The following information
is furnished in response to the comments in your letter to Joseph Pandolfino regarding 22nd Century Group, Inc. (the “Company”)
dated February 28, 2013. In accordance with our subsequent discussions with your colleague, Mr. Donald E. Field, this response
has been limited to the Staff’s Comment #2.

Comment #2 has been
reproduced below in bold italics, followed by our response.

2.	We
note that you are registering the resale of 27,500,000 shares of your common stock on a delayed or continuous basis pursuant to
Rule 415 of the Securities Act of 1933. Given the size of the offering relative to the number of shares of your common stock outstanding
held by non-affiliates, the nature of the offering and the selling stockholders, the transaction appears to be a primary offering.
Because you are not eligible to conduct a primary offering on Form S-3, you are not eligible to conduct a primary at-the-market
offering under Rule 415(a)(4) of the Securities Act of 1933. If you disagree with our analysis, please advise regarding your basis
for determining that the transaction is appropriately characterized as a transaction that is eligible to be made under Rule 415(a)(1)(i)
of the Securities Act of 1933. In your analysis, please address the following among any other relevant factors:

 · The number of shares of your common stock outstanding held by non-affiliates prior to the private
placement of the Series A-1 Preferred Stock and Series A, B and C Warrants on January 11, 2013;

 · The dollar value of the shares of common stock registered in relation to the proceeds that you
received from the selling stockholders for the securities, excluding amounts of proceeds that were returned (or will be returned)
to the selling stockholders and/or their affiliates in fees or other payments;

 9530 Main Street • Clarence,
New York 14031 • TEL 716-270-1523 • FAX 716-877-3064 • www.xxiicentury.com

United States Securities and Exchange Commission

Page 2

 · The relationship of each selling stockholder with the company, including an analysis of whether
each selling stockholder is an affiliate of the company; and

 · Whether or not any of the selling stockholders are in the business of buying and selling securities.

Response

Although we believe
that the offering is a valid secondary offering, the Company and selling stockholders have decided to reduce the size of the offering
significantly. The Company and selling stockholders will amend the Registration Statement to register the 4,166,666 shares of common
stock initially issuable upon conversion of the Series A-1 Preferred Stock and 2,083,334 shares of common stock issuable upon exercise
of the Series B Warrants. Although this amount represents 37.8% of the Company’s pre-transaction float and 15.2% of our total
shares of common stock outstanding after issuance of such shares, since the Series A-1 Preferred Stock and warrants contain exercise
and conversion limitations, the selling stockholders will never own in excess of 9.99% of the Company’s outstanding shares
of common stock.

Analysis

For the reasons set
forth below, the Company respectfully submits that the offering to be registered pursuant to the Registration Statement is eligible
to be made on a shelf basis under Rule 415(a)(1)(i) and that the selling stockholders are not “underwriters” within
the meaning of Section 2(a)(11) of the Securities Act of 1933, as amended (the “Act”).

As an initial matter,
the Company wishes to assert that none of the two selling stockholders is a conduit for the Company, but rather purchased their
securities for their own account. Each of the selling stockholders were immediately at market risk once their securities were purchased,
and such market risk has continued through the time of filing the Registration Statement. Each of the selling stockholders executed
a Securities Purchase Agreement (as described below) for the purchase of their securities which contained representations of the
selling stockholders that stated, among other provisions, that each selling stockholder was purchasing the securities as principal
for its own account for investment only and not with a view toward, or for resale in connection with, the public sale or any distribution
thereof. There is no evidence to suggest that those representations are false and the Company respectfully submits that there is
no basis for concluding that the selling stockholders do not have the intention or ability to hold their shares for investment
purposes for an indefinite period.

There are a number
of reasons why investors would want purchased shares to be registered other than to effect an immediate resale. Many private investment
funds are required to mark their portfolios to market. If portfolio securities are not registered, such investors are typically
required to mark down the book value of those securities to reflect an illiquidity discount. That portfolio valuation does not
depend on whether the selling stockholders intend to dispose of their shares or to hold them for an indefinite period. In addition,
the selling stockholders are fiduciaries for their limited partners and other investors in their funds. As such, the selling stockholders
have a common law duty to act prudently. Accordingly, the Company understands that the selling stockholders wish to have their
securities in a more liquid form, whereas not registering the shares could prevent them from taking advantage of market opportunities
or from liquidating their investment if there is a fundamental shift in their investment judgment about the Company. Finally, registered
shares of many issuers are eligible to be used as margin collateral under the Federal Reserve’s margin regulations. Restricted
securities do not qualify as “margin stock.”

United States Securities and Exchange Commission

Page 3

Transaction Overview

On January 11, 2013,
the Company entered into a Securities Purchase Agreement with certain accredited investors indentified therein (referred to herein
as the selling stockholders), whereby the Company sold 2,500 shares of newly created Series A-1 10% Convertible Preferred Stock
(the “Series A-1 Preferred Stock”) and Warrants (as defined below) for an aggregate purchase price of $2,500,000. The
Company also entered into a Registration Rights Agreement with the selling stockholders whereby the Company agreed to file a registration
statement to register the resale of 200% of the shares of common stock that are potentially issuable under each of
the securities described below as well as anticipated stock dividends over a three year period. The dividends are payable on the
Series A-1 Preferred Stock in cash or stock, at the Company’s option.

The shares of Series
A-1 Preferred Stock are initially convertible into a total of 4,166,666 shares of the Company’s common stock at a conversion
price of $0.60 per share (the “Conversion Price”), subject to future adjustments. The Series A-1 Preferred Stock will
pay a 10.0% annual cash dividend and will have a liquidation preference equal to the stated value of the Series A-1 Preferred Stock
of $1,000 per share plus any accrued and unpaid dividends thereon. The Series A-1 Preferred Stock is not entitled to vote in the
election of directors and generally has no voting rights, other than with respect to certain extraordinary events, such as an amendment
to the rights, preferences or privileges of the Series A-1 Preferred Stock or any liquidation or dissolution of the Company.

The Conversion Price
of the Series A-1 Preferred Stock is subject to adjustment as follows:

    (i)
    on the effective date of a registration statement, the Conversion Price will be reduced to the lesser of (1) the then Conversion Price, as adjusted and taking into consideration any prior resets, (2) the greater of $0.35 (subject to adjustment for reverse and forward stock splits and the like) and 70% of the average of the five (5) trading day volume weighted average prices (“VWAPs”) immediately prior to each such effective date or (3) $0.60 (subject to adjustment for forward and reverse stock splits and the like);

    (ii)
    if on the 180th day immediately following the closing date of January 11, 2013 (the “Closing Date”), 70% of the average of the five (5) trading day VWAPs immediately prior to such date is less than the then Conversion Price, then on such 180th day the Conversion Price shall be reduced to the lesser of (1) the then Conversion Price, as adjusted and taking into consideration any prior resets, (2) the greater of $0.15 (subject to adjustment for reverse and forward stock splits and the like) and 70% of the average of the five (5) trading day VWAPs immediately prior to each such 180th day immediately following the Closing Date or (3) $0.35 (subject to adjustment for forward and reverse stock splits and the like); and

    (iii)
    if all of the shares required to be registered are not registered pursuant to an effective registration statement within the 120th day anniversary of the Closing Date, then on the 180th day and 270th day following the Closing Date, the Conversion Price shall be reduced to the lesser of (1) the then Conversion Price, as adjusted and taking into consideration any prior resets, (2) the greater of $0.15 (subject to adjustment for reverse and forward stock splits and the like) and 70% of the average of the five (5) trading day VWAPs immediately prior to each such date or (3) $0.35 (subject to adjustment for forward and reverse stock splits and the like).

United States Securities and Exchange Commission

Page 4

We also issued to the
selling stockholders a Series A warrant (the “Series A Warrant”), a Series B warrant (the “Series B Warrant”),
and a Series C warrant (the “Series C Warrant”) (with the Series A Warrant, Series B Warrant and Series C Warrant being
collectively referred to herein as the “Warrants,” and together with the Series A-1 Preferred Stock, the “Securities”).
None of the Warrants have adjustments to their exercise price based on the market price of the Company’s common stock rather
each of the Warrants have standard anti-dilution language for future issuances of shares at a price under the conversion price
of such Warrants.

The Series A Warrants
allow the selling stockholders the right to acquire up to an additional 4,166,666 shares of the Company’s common stock at
an exercise price of approximately $0.72 per share over a period of five (5) years, subject to anti-dilution provisions. The Series
A Warrants also allow for such warrants to be exercised on a cashless basis.

The Series B Warrants
allows the selling stockholders a one-year period to exercise an overallotment option as contained in the Series B Warrant to purchase
up to an additional aggregate of 2,083,334 shares of the Company’s common stock at a price of $0.60 per share, subject to
anti-dilution provisions. The Series B Warrants may not be exercised on a cashless basis except only in certain limited circumstances.

In the event the selling
stockholders exercise, in whole or in part the overallotment option as contained in the Series B Warrants, then the selling stockholders
shall have the right to exercise on a pro rata basis the portion of the Series C Warrants issued to the selling stockholders to
acquire up to an additional aggregate of 2,083,334 shares of the Company’s common stock at an exercise price of approximately
$0.72 per share over a period of five (5) years, subject to anti-dilution provisions. The Series C Warrants allow for such warrants
to be exercised on a cashless basis.

The Series A-1 Preferred
Stock and the Warrants contain exercise and conversion limitations providing that a holder thereof may not convert or exercise
(as the case may be) to the extent that, if after giving effect to such conversion or exercise (as the case may be), the holder
or any of its affiliates would beneficially own in excess of 9.99% of the outstanding shares of common stock immediately after
giving effect to such conversion or exercise (as the case may be). This 9.99% blocker is binding and valid (e.g., the provisions
are non-waivable, enforceable, established in the Company’s Certificate of Designations and is applicable to affiliates and
assigns) and effectively eliminates the right of the selling stockholders to acquire in excess of 9.99% of the Company’s
outstanding common stock. Such “blockers” have been upheld by many courts and the factors that indicate that a conversion
cap is binding and valid were discussed in the Brief of the Securities and Exchange Commission, Amicus Curiae in Levy v. Southbrook
International Investments, Ltd. (Sep. 14, 2009).

United States Securities and Exchange Commission

Page 5

Analysis of Purchase Price in Relation
to Proceeds Received by the Company

The Company sold 2,500
shares of Series A-1 Preferred Stock to the selling stockholders for an aggregate purchase price of $2,500,000. The shares of Series
A-1 Preferred Stock are initially convertible into a total of 4,166,666 shares of the Company’s common stock at a conversion
price of $0.60 per share, subject to future adjustments. The Series A Warrants allow the selling stockholders the right to acquire
up to an additional 4,166,666 shares of the Company’s common stock at an exercise price of approximately $0.72 per share
over a period of five (5) years, subject to anti-dilution provisions. The Series A Warrants also allow for such warrants to be
exercised on a cashless basis. The proceeds received by the Company is as follows:

    Proceeds to Company Without Cashless Exercise of Series A Warrants
    Proceeds to Company With Cashless Exercise of Series A Warrants

    Series A-1 Preferred Stock
    $2,500,000
    $2,500,000

    Series A Warrants
    $2,999,999
    N/A

    Total
    $5,499,999
    $2,500,000

The Series B Warrants
allows the selling stockholders a one-year period to exercise an overallotment option as contained in the Series B Warrant to purchase
up to an additional aggregate of 2,083,334 shares of the Company’s common stock at a price of $0.60 per share, subject to
anti-dilution provisions. The Series B Warrants may not be exercised on a cashless basis except only in certain limited
circumstances (if the shares issuable upon exercise are not registered within 18 months following the Closing Date). In the
event the selling stockholders exercise, in whole or in part the overallotment option as contained in the Series B Warrants,
then the selling stockholders shall have the right to exercise on a pro rata basis the portion of the Series C Warrants issued
to the selling stockholders to acquire up to an additional aggregate of 2,083,334 shares of the Company’s common stock at
an exercise price of approximately $0.72 per share over a period of five (5) years, subject to anti-dilution provisions. The Series
C Warrants allow for such warrants to be exercised on a cashless basis. If the Series B Warrants are exercised, the additional
proceeds to the Company are as follows.

    Proceeds to Company Without Cashless Exercise of Series A and C Warrants
    Proceeds to Company With Cashless Exercise of Series A and C Warrants

    Series A-1 Preferred Stock
    $2,500,000
    $2,500,000

    Series A Warrants
    $2,999,999
    N/A

    Series B Warrants
    $1,250,000
    $1,250,000

    Series C Warrants
    $1,500,000
    N/A

    Total
    $8,249,999
    $3,750,000

The Registration Rights
Agreement with the selling stockholders required the Company to register the resale of 200% the shares of com