XXII Proposes 5th Reverse Split to Dodge Nasdaq Delisting

TL;DR

**XXII's repeated reverse splits are a red flag; this stock is a delisting risk and a hard pass for traders.**

AI Summary

22nd Century Group, Inc. (XXII) is seeking stockholder approval for a reverse stock split at a ratio between 1-for-2 and 1-for-200 to regain compliance with Nasdaq's minimum bid price rule of $1.00. This is the fifth reverse stock split since July 2023, following splits of 1-for-15 on July 5, 2023, 1-for-16 on April 2, 2024, 1-for-135 on December 17, 2024, and 1-for-23 on June 20, 2025. As of December 30, 2025, XXII's closing price was $0.7611, below the Nasdaq requirement. The company also seeks approval for sections of Series A Convertible Preferred Stock, amendments to 10,028,302 outstanding warrants issued in August 2025 to add anti-dilution provisions, and a potential future offering, all to comply with Nasdaq Listing Rules. The Special Meeting of stockholders is scheduled for February 20, 2026, in El Paso, Texas, with a record date of January 2, 2026. The Board of Directors, led by Chairman and CEO Lawrence D. Firestone, believes these actions are in the best interest of the Company and its stockholders to avoid delisting and enhance market appeal.

Why It Matters

This filing reveals 22nd Century Group's desperate struggle to maintain its Nasdaq listing, proposing a fifth reverse stock split in less than two years. For investors, this signals significant underlying issues with the company's valuation and operational performance, as repeated splits often fail to provide sustained price increases. Employees and customers might view this as a sign of instability, potentially impacting morale and business relationships. In the broader market, this highlights the challenges smaller companies face in meeting listing requirements, especially in competitive sectors, and could deter new investment in similar low-priced securities.

Risk Assessment

Risk Level: high — The company has already effected four reverse stock splits (1-for-15, 1-for-16, 1-for-135, 1-for-23) since July 2023, yet its common stock closed at $0.7611 on December 30, 2025, still below the Nasdaq $1.00 minimum bid price. This history of repeated, aggressive reverse splits without sustained price recovery indicates severe and persistent challenges in maintaining market value and Nasdaq compliance, posing a high risk of delisting.

Analyst Insight

Investors should exercise extreme caution and consider divesting, as the company's repeated reliance on reverse stock splits to maintain listing suggests fundamental business challenges. Avoid new positions until there's clear evidence of sustained operational improvement and a stable stock price above Nasdaq's minimum bid requirement.

Key Numbers

• $0.7611 — Closing price of common stock (As of December 30, 2025, below Nasdaq's $1.00 minimum bid price)
• 1-for-2 to 1-for-200 — Proposed reverse stock split ratio (Discretionary range for the Board of Directors)
• 1-for-15 — Reverse stock split ratio (Effected on July 5, 2023)
• 1-for-16 — Reverse stock split ratio (Effected on April 2, 2024)
• 1-for-135 — Reverse stock split ratio (Effected on December 17, 2024)
• 1-for-23 — Reverse stock split ratio (Effected on June 20, 2025)
• 10,028,302 — Outstanding warrants (Issued in August 2025, proposed for anti-dilution amendment)
• 7,652,661 — Shares of common stock outstanding (As of December 30, 2025, entitled to vote)
• February 20, 2026 — Special Meeting date (Date for stockholders to vote on proposals)
• January 2, 2026 — Record date (Date for determining stockholders eligible to vote)

Key Players & Entities

• 22nd Century Group, Inc. (company) — Registrant seeking stockholder approval
• Nasdaq (regulator) — Exchange with listing rules (Rule 5550(a)(2))
• Lawrence D. Firestone (person) — Chairman and Chief Executive Officer
• Jonathan Staffeldt (person) — General Counsel
• SEC (regulator) — Promulgates 'penny stock' regulations
• OTC Markets Group (company) — Inter-dealer electronic quotation and trading system
• Nevada (regulator) — State of incorporation, governing reverse split laws

FAQ

Risk Factors

• Failure to Maintain Nasdaq Listing [high — regulatory]: The company's common stock is trading below the $1.00 minimum bid price required by Nasdaq. This DEF 14A seeks approval for a reverse stock split (1-for-2 to 1-for-200) to regain compliance. Failure to achieve compliance through this or other means could lead to delisting, significantly impacting liquidity and investor confidence.
• Dilution from Preferred Stock and Warrants [high — financial]: The company is seeking approval for sections of its Series A Convertible Preferred Stock and amendments to 10,028,302 outstanding warrants to add anti-dilution provisions. These actions, while aimed at compliance, could lead to significant dilution of common stock if not managed carefully, impacting existing shareholders.
• History of Reverse Stock Splits [medium — financial]: This proposed reverse stock split is the fifth since July 2023, following splits of 1-for-15 (July 2023), 1-for-16 (April 2024), 1-for-135 (December 2024), and 1-for-23 (June 2025). This frequent need for reverse splits indicates persistent low stock price and potential underlying business challenges.
• Compliance with Nasdaq Listing Rules [high — regulatory]: Multiple proposals in this filing are directly related to complying with Nasdaq Listing Rules, including the reverse stock split, Series A Preferred Stock terms, warrant amendments, and a potential future offering. Failure to meet these requirements poses a direct threat to the company's listing.

Industry Context

22nd Century Group operates in the highly regulated and competitive tobacco and nicotine product industry, focusing on reduced-harm alternatives. The industry is undergoing significant shifts driven by evolving consumer preferences towards vaping and reduced-nicotine products, alongside increasing regulatory scrutiny from bodies like the FDA. Competitors range from large multinational tobacco companies to smaller, specialized e-cigarette and nicotine pouch manufacturers.

Regulatory Implications

The company faces substantial regulatory risk, particularly from the FDA's oversight of tobacco and nicotine products. Compliance with evolving regulations, such as potential menthol bans or stricter marketing rules, can significantly impact product sales and development. Furthermore, maintaining listing on major exchanges like Nasdaq requires adherence to specific financial and governance standards, which the company is actively seeking to address.

What Investors Should Do

1. Vote FOR Proposals 1, 2, 3, and 4.
2. Carefully review the potential dilution from the Series A Preferred Stock and warrant amendments.
3. Monitor the company's ability to achieve sustainable profitability and stock price appreciation post-compliance.

Key Dates

• 2026-02-20: Special Meeting of Stockholders — Stockholders will vote on critical proposals, including a reverse stock split, to maintain Nasdaq compliance.
• 2026-01-02: Record Date — Determines which stockholders are eligible to vote at the Special Meeting.
• 2025-12-30: Closing price of common stock — Reported at $0.7611, below Nasdaq's $1.00 minimum bid price requirement.
• 2025-08-01: Issuance of August Warrants — 10,028,302 warrants were issued, now requiring amendment for anti-dilution provisions.
• 2025-06-20: Reverse Stock Split — A 1-for-23 reverse stock split was effected, indicating ongoing struggles with stock price.
• 2024-12-17: Reverse Stock Split — A 1-for-135 reverse stock split was effected, highlighting persistent low stock price issues.

Glossary

Reverse Stock Split

A corporate action where a company reduces the number of its outstanding shares by consolidating them into fewer, proportionally more valuable shares. (Proposed to increase the stock price per share to meet Nasdaq's minimum bid price requirement.)

Nasdaq Minimum Price Rule

A rule set by the Nasdaq stock exchange requiring listed companies to maintain a minimum bid price for their common stock, typically $1.00. (The company is currently non-compliant with this rule, necessitating the reverse stock split.)

Series A Convertible Preferred Stock

A class of preferred stock that can be converted into a predetermined number of common stock shares. (Certain provisions of this stock could lead to common stock issuance below the Nasdaq minimum price, requiring stockholder approval.)

Anti-dilution provisions

Clauses in financial instruments (like warrants or preferred stock) designed to protect investors from a decrease in the value of their investment due to the issuance of new shares by the company at a lower price. (Amendments are sought for outstanding warrants to include these provisions, likely to protect against further dilution.)

DEF 14A

A filing with the U.S. Securities and Exchange Commission (SEC) that provides detailed information to shareholders about matters to be voted on at an annual or special meeting. (This document outlines the proposals and rationale for the upcoming Special Meeting of Stockholders.)

Quorum

The minimum number of shareholders or directors required to be present at a meeting for the meeting to be valid and for business to be transacted. (One-third (33.33%) of the voting power of common stock must be present, in person or by proxy, for the Special Meeting to proceed.)

Street Name

When shares of stock are held by a broker or other nominee on behalf of the beneficial owner, rather than directly in the owner's name. (Explains how shareholders who do not hold shares directly must vote their shares.)

Year-Over-Year Comparison

This DEF 14A filing indicates a worsening financial situation compared to previous periods, primarily evidenced by the company's continued struggle to maintain the Nasdaq minimum bid price. The current closing price of $0.7611 as of December 30, 2025, necessitates a fifth reverse stock split since July 2023, with a proposed ratio of 1-for-2 to 1-for-200. This filing also highlights the need to amend outstanding warrants and address Series A Convertible Preferred Stock terms to meet Nasdaq listing rules, suggesting increased financial and regulatory pressures.

Key Financial Figures

• $1.00 m — rice of our common stock to satisfy the $1.00 minimum closing bid price required to try
• $0.7611 — d closing price of our common stock was $0.7611. A delisting of our common stock may ma

Filing Documents

• formdef14a.htm (DEF 14A) — 253KB
• formpre14a_001.jpg (GRAPHIC) — 6KB
• formpre14a_002.jpg (GRAPHIC) — 1KB
• formpre14a_003.jpg (GRAPHIC) — 1KB
• formpre14a_004.jpg (GRAPHIC) — 1KB
• formpre14a_005.jpg (GRAPHIC) — 2KB
• proxy_001.jpg (GRAPHIC) — 492KB
• proxy_002.jpg (GRAPHIC) — 219KB
• 0001493152-25-029651.txt ( ) — 1251KB

From the Filing

DEF 14A 1 formdef14a.htm DEF 14A UNITED SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Exchange Act of 1934 Filed by the Registrant Filed by a Party other than the Registrant Check the appropriate box: Preliminary Proxy Statement Confidential, for Use of the Commission Only (as permitted by Rule 14a-6I(2)) Definitive Proxy Statement Definitive Additional Materials Soliciting Material Pursuant to §240.14a-12-6I(2)) 22nd Century Group, Inc. (Name of Registrant as Specified in its Charter) (Name of Person(s) Filing Proxy Statement, if Other Than the Registrant) Payment of Filing Fee (Check the appropriate box): No fee required. Fee paid previously with preliminary materials. Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11. 321 Farmington Road, Mocksville, North Carolina 27028 Notice of Special Meeting of Stockholders and Proxy Statement TO THE HOLDERS OF COMMON STOCK: PLEASE TAKE NOTICE that a Special Meeting of stockholders of 22nd Century Group, Inc. (the “Company”) will be held at 5200 N. Mesa St., Suite B104, El Paso, Texas 79912 on Friday, February 20, 2026, beginning at 10:00 A.M, Eastern Time. The meeting will be held for the following purposes: 1.. To approve an amendment to our Articles of Incorporation, as amended, to effect a reverse stock split of our outstanding common stock at a ratio between 1-for-2 and 1-for-200, to be determined at the discretion of our Board of Directors (the “Reverse Split”), for the purpose of complying with the Nasdaq Listing Rules, subject to the Board’s discretion to abandon such amendment (Proposal 1). 2. To approve sections of the Series A Convertible Preferred Stock (the “Series A Preferred”) that could cause shares of common stock to be issued below the Nasdaq Minimum Price in accordance with Nasdaq Listing Rules (Proposal 2). 3. To approve an amendment to 10,028,302 outstanding warrants issued in August 2025 to add anti-dilution provisions (the “August Warrants”) in accordance with Nasdaq Listing Rules (Proposal 3). 4. To approve a potential future offering in accordance with Nasdaq Listing Rules (Proposal 4). 5. To approve the adjournment of the meeting, if necessary or advisable, to solicit additional proxies in favor of Proposals 1, 2, 3 or 4 (Proposal 5). The stockholders of record at the close of business on January 2, 2026 will be entitled to vote at the Special Meeting. By Order of the Board of Directors, Lawrence D. Firestone Chairman and Chief Executive Officer Dated: December 30, 2025 PROXY STATEMENT | ii MEETING INFORMATION: DATE: Friday, February 20, 2026 TIME: 10:00 A.M., Eastern Time PLACE: The meeting will be held at 5200 N. Mesa St., Suite B104, El Paso, Texas 79912. HOW TO VOTE: Your vote is important. You are eligible to vote if you were a stockholder of record at the close of business on January 2, 2026. BY INTERNET www.proxyvote.com BY PHONE Call 1.800.690.6903 BY MAIL Complete, sign and return by free post IN PERSON Attend the Special Meeting PROXY STATEMENT | iii Table of Contents Frequently Asked Questions Regarding Special Meeting Procedures 1 Proposal One: APPROVAL OF THE AMENDMENT TO EFFECT THE REVERSE STOCK SPLIT 4 Proposal Two: APPROVAL OF SECTIONS OF THE SERIES A CONVERTIBLE PREFERRED STOCK 12 Proposal Three: APPROVAL OF AN AMENDMENT TO THE 10,028,302 OUTSTANDING WARRANTS ISSUED IN AUGUST 2025 14 Proposal Four: APPROVAL OF A POTENTIAL FUTURE OFFERING IN ACCORDANCE WITH NASDAQ LISTING RULES 15 Proposal Five: ADJOURNMENT OF THE MEETING, IF NECESSARY OR ADVISABLE, TO SOLICIT ADDITIONAL PROXIES 18 Beneficial Ownership 19 Stockholder Proposals and Communications with the Board of Directors 20 Other Matters 20 PROXY STATEMENT | iv Frequently Asked Questions Regarding Special Meeting Procedures Q: Why did I receive these materials? The Board of Directors of 22nd Century Group, Inc. is soliciting proxies for the Special Meeting of Stockholders (Special Meeting) to be held on February 20, 2026 in person. You are receiving a proxy statement because you owned shares of our common stock on January 2, 2026, and that entitles you to vote at the meeting. By use of a proxy, you can vote whether or not you attend the meeting. The proxy materials include this proxy statement for the Special Meeting and a proxy card or voting instruction form for the Special Meeting. Q: What information is contained in this proxy statement? The information in this proxy statement relates to the proposals to be voted on at the Special Meeting, the approval of the Reverse Split (Proposal 1), the Series A Preferred (Proposal 2), the anti-dilution adjustments in the August Warrants (Proposal 3), the potential new offering (Proposal 4) and the adjournment of the meeting, if necessary or advisab

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View this DEF 14A filing on SEC EDGAR