0001104659-23-109884 Sample Contracts

COMMON STOCK PURCHASE WARRANT
Common Stock Purchase Warrant • October 18th, 2023 • 22nd Century Group, Inc. • Cigarettes • New York

THIS COMMON STOCK PURCHASE WARRANT (the “Warrant”) certifies that, for value received, _____________ or its assigns (the “Holder”) is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set forth, at any time on or after the date hereof (the “Initial Exercise Date”) and on or prior to 5:00 p.m. (New York City time) on October 19, 2028 (the “Termination Date”) but not thereafter, to subscribe for and purchase from 22nd Century Group, Inc., a Nevada corporation (the “Company”), up to [______] shares (as subject to adjustment hereunder, the “Warrant Shares”) of Common Stock. The purchase price of one share of Common Stock under this Warrant shall be equal to the Exercise Price, as defined in Section 2(b).

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SECURITIES PURCHASE AGREEMENT
Securities Purchase Agreement • October 18th, 2023 • 22nd Century Group, Inc. • Cigarettes • New York

This Securities Purchase Agreement (this “Agreement”) is dated as of October 17, 2023, between 22nd Century Group, Inc., a Nevada corporation (the “Company”), and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively the “Purchasers”).

PRE-FUNDED COMMON STOCK PURCHASE WARRANT 22ND CENTURY GROUP, inc.
Pre-Funded Common Stock Purchase Warrant • October 18th, 2023 • 22nd Century Group, Inc. • Cigarettes • New York

THIS PRE-FUNDED COMMON STOCK PURCHASE WARRANT (the “Warrant”) certifies that, for value received, _____________ or its assigns (the “Holder”) is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set forth, at any time on or after the date set forth above (the “Initial Exercise Date”) and until this Warrant is exercised in full (the “Termination Date”) but not thereafter, to subscribe for and purchase from 22nd Century Group, Inc., a Nevada corporation (the “Company”), up to [______] shares (as subject to adjustment hereunder, the “Warrant Shares”) of Common Stock. The purchase price of one share of Common Stock under this Warrant shall be equal to the Exercise Price, as defined in Section 2(b).

PLACEMENT AGENT COMMON STOCK PURCHASE WARRANT 22ND CENTURY GROUP, inc.
Placement Agent Common Stock Purchase Warrant • October 18th, 2023 • 22nd Century Group, Inc. • Cigarettes • New York

THIS PLACEMENT AGENT COMMON STOCK PURCHASE WARRANT (the “Warrant”) certifies that, for value received, _____________ or its assigns (the “Holder”) is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set forth, at any time on or after the Authorized Share Increase Date (the “Initial Exercise Date”) and on or prior to 5:00 p.m. (New York City time) on October 17, 2028 (the “Termination Date”) but not thereafter, to subscribe for and purchase from 22nd Century Group, Inc., a Nevada corporation (the “Company”), up to [______] shares (as subject to adjustment hereunder, the “Warrant Shares”) of Common Stock. The purchase price of one share of Common Stock under this Warrant shall be equal to the Exercise Price, as defined in Section 2(b). This Warrant is being issued pursuant to that certain Engagement Agreement by and between the Company and Dawson James Securities, Inc. dated as of June 19, 2023, as amended on July 19, 2023 and October 16,

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