Another Case for Challenging 280E: HHS’s Authority and the Collapse of Drug Scheduling Powers

Another Case for Challenging 280E: HHS’s Authority and the Collapse of Drug Scheduling Powers

The cannabis and psychedelics industries are currently subject to one of the most punitive tax codes in the U.S. Internal Revenue Code § 280E, which disallows deductions and credits for businesses trafficking in Schedule I or II controlled substances. Most cannabis operators have resigned themselves to this burden, awaiting the DEA’s decision to reschedule cannabis to Schedule III following a historic recommendation by the Department of Health and Human Services (HHS). But a recent forthcoming article in the Yale Law Journal Forum, Separation of Drug Scheduling Powers by Mason Marks, may offer the most significant legal justification to date for operators to challenge 280E proactively, rather than passively waiting on DEA action.

HHS Has Final Say on Scientific and Medical Scheduling

Marks’ analysis of the CSA and its legislative history clarifies that Congress deliberately split authority over drug scheduling between the Department of Justice (DOJ)/DEA and HHS. Specifically:

• HHS is granted exclusive authority over scientific and medical determinations.

• The DEA’s role is limited to nonmedical, law enforcement-related considerations.

• HHS recommendations on scientific matters are binding on the DEA under 21 U.S.C. § 811(b).

• HHS possesses not only a control veto (to stop a drug from being scheduled) but also a scheduling veto (to prevent movement between schedules contrary to scientific advice).

Despite this statutory structure, decades of bureaucratic drift and judicial deference to DEA interpretations have led to law enforcement dominance over drug scheduling. As a result, cannabis and substances like psilocybin remain scheduled inconsistently with both science and public health considerations.

The Misapplication of 280E in Light of HHS’s Determination

The IRS’s application of 280E hinges on a key assumption: that cannabis is a Schedule I drug under federal law. But if DEA lacks independent authority to schedule drugs contrary to binding HHS recommendations, then once HHS recommended moving cannabis to Schedule III, that decision should have been final, especially if DEA has no legal discretion to override it.

The Yale article asserts that:

• Courts have wrongly allowed DEA to perform its own scientific analyses and ignore HHS recommendations.

• HHS’s August 2023 recommendation to reclassify cannabis to Schedule III was based on robust scientific review and a new two-part test for “currently accepted medical use” that no longer depends on FDA approval.

• OLC (Office of Legal Counsel) has tried to limit the binding nature of HHS’s recommendations to pre-rulemaking stages, but this interpretation contradicts the CSA’s plain language and legislative history.

Implications for Cannabis Operators: Time to Challenge 280E

If HHS holds ultimate scientific authority, and if its recommendation to reschedule cannabis is indeed binding under the CSA, then 280E arguably no longer applies to cannabis, regardless of whether DEA has completed rulemaking. This view radically shifts the legal terrain and offers cannabis operators a defensible rationale for:

• Filing amended tax returns that claim deductions previously disallowed under 280E.

• Using 471(c) and other accounting methods to recharacterize expenses.

• Proactively excluding 280E adjustments from current and future returns.

Cannabis companies can no longer afford to wait. Leading multistate operators like Trulieve and Curaleaf have already filed amended returns and are taking the position that 280E no longer applies. The legal scholarship now supports this strategy, not just as a tax position, but as a necessary correction of a constitutional and administrative misinterpretation that has harmed public health and economic development for decades.

Conclusion: The Time for Passive Compliance is Over

Mason Marks’ essay makes it clear: the CSA does not give DEA the last word on drug scheduling, HHS does. The idea that we must wait for DEA rulemaking to resolve the application of 280E is a fiction that only continues to harm legitimate businesses. The statutory tools, legal reasoning, and public health imperatives now all point toward the same conclusion: cannabis operators have every right, and perhaps a fiduciary duty, to challenge 280E by filing amended returns and claiming their full tax deductions.

See Separation of Drug Scheduling Powers, by the THE YALE LAW JOURNAL FORUM:

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The Fight Over Cannabis Rescheduling: Progress, Setbacks, and the Battle Ahead

The Fight Over Cannabis Rescheduling: Progress, Setbacks, and the Battle Ahead

For decades, the Drug Enforcement Administration (DEA) has relied on a rigid five-part test to determine whether a drug has a “currently accepted medical use” under the Controlled Substances Act (CSA). This framework, first articulated in a 1992 Federal Register notice (57 FR 10499), established five strict criteria that cannabis advocates have long argued were designed to prevent rescheduling rather than assess medical legitimacy. The five factors required that a drug’s chemistry be known and reproducible, that there be adequate safety studies, that well-controlled studies prove efficacy, that the drug be accepted by qualified experts, and that the scientific evidence be widely available. This narrow interpretation has been a major obstacle in every attempt to remove cannabis from Schedule I of the CSA.

That changed with an April 11, 2024, opinion from the Department of Justice’s Office of Legal Counsel (OLC). The OLC determined that the DEA’s five-part test was “impermissibly narrow” and instead endorsed a two-part inquiry developed by the Department of Health and Human Services (HHS). This opinion was released to the public on May 16, 2024, alongside Attorney General Merrick Garland’s notice of proposed rulemaking to reschedule cannabis to Schedule III (DOJ, 2024). The two-part test presents a far more flexible approach: first, it asks whether a drug has widespread current medical use among licensed healthcare providers; second, it assesses whether there is credible scientific support for at least one of its medical applications. Crucially, this standard does not require FDA approval, removing one of the biggest roadblocks that had prevented cannabis from being recognized as medicine under federal law.

Applying the two-part inquiry to cannabis makes it clear why HHS recommended rescheduling. The widespread use of cannabis for medical purposes is undeniable. Thirty-eight states, three U.S. territories, and Washington, D.C. have legalized medical cannabis programs, with millions of patients obtaining recommendations from licensed healthcare providers. State medical boards regulate its use, and its medical applications are increasingly accepted in professional healthcare settings. The second prong of the inquiry—credible scientific support—has also been met. A growing body of peer-reviewed research supports cannabis’s effectiveness in treating conditions such as chronic pain, chemotherapy-induced nausea, epilepsy, and multiple sclerosis. In 2017, the National Academies of Sciences, Engineering, and Medicine (NASEM) reviewed the literature and concluded that substantial evidence supports cannabis’s medical efficacy (NASEM, 2017). Furthermore, the FDA has already approved cannabis-derived medications like Epidiolex, which contains CBD and is used to treat epilepsy, as well as synthetic THC such as dronabinol and nabilone for nausea and weight loss in patients undergoing chemotherapy or suffering from AIDS-related wasting syndrome.

This shift in policy, specifically moving away from the DEA’s five-part test in favor of the more accurate and inclusive two-part test recommended by HHS, has significant tax implications for the cannabis industry. Section 280E of the Internal Revenue Code disallows deductions for ordinary business expenses for businesses trafficking in controlled substances that fit “the meaning” of a Schedule I or II drug under the Controlled Substances Act—not simply because they are classified as such. Therefore, given the determination offered by the OLC, there is a strong argument that 280E never truly applied to cannabis, as it never actually met the legal definition of a Schedule I or II drug. This interpretation challenges the longstanding tax burdens placed on cannabis businesses and raises further questions about the enforcement of 280E moving forward.

But the battle is not over. With the new administration, there has been a new wave of attempts by Congress to stifle rescheduling. One such effort is a measure introduced by Rep. Andrew Clyde (R-GA), which seeks to strip the U.S. attorney general’s authority to facilitate drug scheduling decisions and block the use of a revised scientific review standard for “currently accepted medical use” that underpinned the recent cannabis rescheduling proposal. Clyde’s amendment, attached to a bill focused on fentanyl, would require that scheduling decisions be made solely by the DEA administrator, preventing delegation of this authority to any other Department of Justice official. However, it is noteworthy that Rep. Clyde has since withdrawn this amendment, though the potential for similar legislative efforts remains. Additionally, the amendment would mandate that any determination of a drug’s medical value adhere to the restrictive five-part test originally used to deny rescheduling in 1992—effectively undermining the legal rationale for moving cannabis to Schedule III.

Beyond rescheduling battles, cannabis businesses face another looming threat: congressional changes to tax policy. Last week, Sen. James Lankford (R-OK) introduced a bill aimed at ensuring that cannabis businesses remain ineligible for federal tax deductions, even if cannabis is rescheduled to a lower tier under the Controlled Substances Act. The measure, co-sponsored by Sen. Pete Ricketts (R-NE), would explicitly prevent cannabis businesses from deducting ordinary business expenses, a benefit normally afforded to other industries. “Marijuana doesn’t make our families stronger, our streets safer, or our workplaces more productive. Businesses who sell federally illegal drugs—including marijuana businesses—shouldn’t get federal tax breaks,” Lankford stated in a press release. The bill directly targets the potential tax relief that cannabis businesses might receive under Schedule III, reinforcing the punitive nature of current federal cannabis policy.

However, as Jed Green of Oklahomans for Responsible Cannabis Action pointed out, much of what Lankford’s bill seeks to achieve is already in place through Section 280E of the tax code. “What that means is that some growers can deduct taxes. However, your dispensaries, any advertising, budtenders, none of that can be deducted,” Green explained. “So, he’s kind of beating a dead horse and is against the tide here, which there are 22 other states that have allowed this.”

As of January 2025, the DEA’s rescheduling process has encountered significant delays. A hearing scheduled for January 21, 2025, was postponed pending the resolution of an appeal filed by a party in the proceedings. This postponement has indefinitely delayed the rescheduling process, with the DEA and involved parties required to provide a joint status update every 90 days until the matter is resolved. Compounding these delays, the appointment of Terrance C. Cole as the new acting administrator of the DEA has raised concerns among cannabis advocates due to his long-standing opposition to cannabis reform.. These developments have cast uncertainty over the future of federal cannabis rescheduling efforts. However, as the battle over federal cannabis policy is far from over. However, for the first time in decades, the legal framework is shifting in a way that favors medical cannabis access rather than obstructing it. The days of the DEA using an impermissibly narrow test to block rescheduling may finally be coming to an end—but new legislative threats continue to emerge, reminding us that the fight for fair cannabis policy is far from finished.

References

• Marijuana Moment (2025). GOP Congressman Withdraws Amendment Aimed At Undermining Marijuana Rescheduling Process. Retrieved from marijuanamoment.net

• Marijuana Moment (2025). DEA Cannabis Rescheduling Hearing Postponed Amid Leadership Transition. Retrieved from marijuanamoment.net

• Department of Justice (2024). Questions Related to Potential Rescheduling of Marijuana. Retrieved from justice.gov

• National Academies of Sciences, Engineering, and Medicine (2017). The Health Effects of Cannabis and Cannabinoids: The Current State of Evidence and Recommendations for Research. Washington, DC: The National Academies Press. Retrieved from NCBI

• Federal Register (1992). Denial of Petition to Reschedule Marijuana (57 FR 10499). Retrieved from federalregister.gov

Challenging 280E: Justifications for Taking Deductions and Amending Tax Returns

MJBIZ Webinar: Challenging 280E: Justifications for Taking Deductions and Amending Tax Returns

Challenging 280E: Justifications for Taking Deductions and Amending Tax Returns

Challenging 280E: Justifications for Taking Deductions and Amending Tax Returns

With recent shifts in federal policy, cannabis businesses face an unprecedented opportunity to challenge 280E. Despite the IRS’s warnings of increased enforcement against companies that do not comply, the cannabis industry is taking bold action by amending tax returns and refusing to reduce deductions.

Numerous cannabis operators, including Curaleaf, Cresco Labs, and Ascend Wellness, have announced their intentions to prepare tax returns without reducing deductions for 280E. Sparked by Trulieve’s receipt of a $113,000,000 refund following amended filings, many businesses are now amending their own returns to reclaim lost deductions. Additionally, industry leaders like Canna Provisions and Verano Holdings Corp. have taken their case to the U.S. Court of Appeals, asserting that the Controlled Substances Act (CSA) should not apply in states with regulated cannabis industries. Finally, a compelling argument asserts that cannabis never met the criteria for a Schedule I drug designation. The DOJ itself concluded that the DEA’s test for defining cannabis as a Schedule I substance was “impermissibly narrow,” raising questions about whether 280E applies to cannabis as the code is written.

Join us for the upcoming webinar, “Challenging 280E: Justifications for Taking Deductions and Amending Tax Returns.” This in-depth session will dive into:

· A historical overview of the cannabis industry’s strategies to mitigate the effects of 280E, including discussions and applications of tax code sections 263(a), 471(a), and 471(c).

· The justifications being used by MSOs like Trulieve to amend tax returns and reclaim disallowed deductions.

· The lawsuit pursued by Verano Holdings and Canna Provisions and its implications if successful.

· Recent Supreme Court actions that undermine the applicability of the CSA and, therefore, 280E.

· The implications of the imminent reclassification of cannabis to a Schedule III substance.

· The statutes of limitations for amending returns and the potential risks of taking bold actions.

MJ BIzcon with Justin

Justin to be speaking at MJBizCon Dec 3-6.

The Future of Cannabis Investment in a Post-280E Landscape

We’re thrilled to announce that Calyx CPA’s own CEO, Justin Botillier, will be speaking at MJBizCon 2024 in Las Vegas! Join Justin and other industry leaders as they dive into “Understanding the Investment Landscape in a Post-280E Environment.” This is an invaluable opportunity for anyone invested in the cannabis sector to gain insight into what the future holds as the regulatory landscape evolves.

📅 When: Tuesday, Dec 3 at 11:20 AM
📍 Where: Las Vegas Convention Center
🎟️ Get 20% off your ticket with the code MIGL24SPK Sign Up Here

This panel will feature experts from across the cannabis finance and investment sectors, including:

  • Melissa Diaz – Rebel Rock
  • Josephine Giordano – BeachFleischman PLLC
  • Adam Goers – The Cannabist Company

Whether you’re looking to refine your investment strategy or understand the implications of shifting tax policies, this discussion is not to be missed. Secure your spot today and join us in navigating this transformative time for the cannabis industry!

The Unfair Burden of Measure 119

The Unfair Burden of Measure 119: Why Oregon’s Cannabis Industry Needs Your Voice

The Unfair Burden of Measure 119

The Unfair Burden of Measure 119: Why Oregon's Cannabis Industry Needs Your Voice

As voters head to the polls, an important issue is on the table that could significantly affect Oregon’s cannabis industry. Measure 119 proposes a requirement for cannabis businesses, including dispensaries and processors, to allow unionizing efforts while exempting the alcohol industry from similar obligations. This creates an unfair burden on cannabis operators in an already highly competitive market.

The Struggles of Cannabis Businesses

Dispensaries and processing businesses in the cannabis sector often operate with narrow profit margins and face intense competition. The addition of compliance costs and administrative demands associated with unionization could prove particularly challenging, especially for smaller businesses with limited resources.

Imbalanced Regulations

What makes this situation even more concerning is the regulatory imbalance created by this measure. While cannabis businesses would be compelled to provide employer neutrality and grant union access to employees, alcohol businesses, regulated by the same agency, the Oregon Liquor and Cannabis Commission (OLCC) are not subject to these requirements. This discrepancy unfairly impacts the cannabis industry, putting its operators at a disadvantage compared to their alcohol counterparts.

Take Action

Calyx CPA encourages all voters to consider the implications of Measure 119 carefully. By voting NO by November 5th, you can help prevent the undue burden on Oregon’s cannabis dispensaries and processors, ensuring a more level playing field in this competitive market. Your voice matters, let’s protect the future of Oregon’s cannabis industry together!

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Psychedelics Best Business Practices

Psychedelics Best Business Practices | Remind Webinar Oct 31st

Psychedelics Best Business Practices

Join us for an enlightening session on October 30, 2024, at 2 p.m. ET as we dive deep into the complex world of psychedelic businesses on LinkedIn Live!

This exclusive event features a panel of industry experts ready to share their invaluable knowledge on taxes, insurance, and legal issues specific to the psychedelic sector.

Our distinguished panelists include:

Justin Botillier, CEO of Calyx CPA, who brings a wealth of experience in tax strategies tailored for emerging industries.

Jodi Green, Managing Partner at Antithesis Law, PC, an authority on legal frameworks that guide psychedelic business practices.

Eric Rahn, Founder of Rahn & Associates PSYINS, specializing in insurance solutions for the unique challenges faced by psychedelic entrepreneurs.

Moderated by the insightful Keyaira Lock Adewunmi, Founder of Spice & Sage, this session promises to provide you with the guidance needed to navigate the evolving landscape of psychedelic commerce.

Don’t miss out on this opportunity to gain expert perspectives and ask your burning questions!

Register Here to join us live! 

psilocybin - Oregon

Advocating for Flexibility: Oregon’s Psilocybin Industry Must Adapt to Stay Ahead

Advocating for Flexibility: Oregon's Psilocybin Industry Must Adapt to Stay Ahead

psilocybin - Oregon

To the Oregon psilocybin industry, the upcoming public comment period offers a critical opportunity to advocate for more flexible regulations that align with Colorado’s model and maintain Oregon’s advantage as a pioneering state in this field. As Colorado finalizes its Natural Medicine Health Act, several provisions might challenge Oregon’s first-to-market position if not addressed proactively.

Here are key points to consider:

1. Expand the Scope of Allowed Activities and Substances: Although Colorado’s framework currently focuses on psilocybin, it’s poised to expand to other natural medicines, like DMT, ibogaine, and certain forms of mescaline. Advocating for a similar framework in Oregon could position the state to support a broader spectrum of natural medicines. This could help Oregon maintain its role as a leader in plant medicine, offering diverse therapeutic options and attracting practitioners and clients from other states.

2. Allow for Flexibility in Service Settings: Colorado permits licensed facilitators to operate outside of designated healing centers, enabling them to provide services in homes, healthcare facilities, and other community settings. This flexibility enhances accessibility and affordability for clients. Oregon’s strict requirement for services to be performed exclusively in licensed service centers could limit access and create higher costs. By expanding the types of permissible service settings, Oregon can ensure broader, more equitable access across the state.

3. Local Control: Colorado’s regulations prevent local governments from entirely prohibiting healing centers but allow them to regulate time, place, and manner of operations. In Oregon, several local jurisdictions have opted out, reducing accessibility for some residents. A statewide policy preventing outright bans but allowing local time and manner restrictions could increase service availability and foster greater industry growth in Oregon.

4. Decriminalization of Personal Use: Colorado has decriminalized personal possession, cultivation, and use of natural medicines like psilocybin, which allows adults 21 and older to possess and use these substances without criminal penalties. While Oregon initially passed Measure 110, which decriminalized small quantities of controlled substances, this has since been repealed, making even small quantities of psychedelics illegal once more. To maintain Oregon’s progressive stance on natural medicine, the state should consider adopting a targeted decriminalization policy specifically for psychedelics, aligning more closely with Colorado’s approach. This move would support safe personal use, encourage responsible exploration of plant medicines, and reduce unnecessary criminalization for low-level possession.

5. Licensing Flexibility: Both states require separate licenses for cultivation, manufacturing, and administration, but Colorado allows licensed professionals from other industries (such as healthcare and mental health services) to operate within licensed healing centers. Oregon could benefit from similar provisions, allowing therapists, counselors, and other licensed professionals to offer complementary services within psilocybin centers. This could encourage a holistic approach to mental health, integrate broader professional expertise, and attract a diverse range of clients.

6. Cultural and Indigenous Sensitivity: Colorado has established a Tribal and Indigenous Working Group to prevent cultural misappropriation and promote respectful practices within the industry. Oregon could incorporate similar measures to ensure that the industry respects Indigenous traditions and involves communities in regulatory development. This approach not only acknowledges cultural heritage but also strengthens the ethical framework for natural medicine services.

By encouraging these adjustments, the Oregon psilocybin industry can leverage public feedback to adopt a more inclusive and flexible framework. This can help sustain Oregon’s competitive edge and expand its reach as other states begin to explore similar regulatory programs.

Sources: Zuber Lawler, “5 Takeaways from Colorado’s Proposition 122 – The Natural Medicine Health Act” – Highlights the provisions for personal use, flexibility in service locations, and future potential expansion to other substances under the NMHA.

Vicente LLP, “The Ultimate Guide to SB23-290, Colorado’s Natural Medicine Regulation and Legalization Bill” – Details on the regulatory framework for licensed facilitators, Indigenous and cultural sensitivity provisions, and licensing structures for natural medicines.

Healing Maps, “Psilocybin Laws in Colorado and Oregon: What’s the Difference?” – Compares Oregon’s psilocybin regulations to Colorado’s, covering topics like local control, decriminalization, and service settings.

The Future of Hemp in Oregon: A Call to Action with Courtney Moran

The Future of Hemp in Oregon: A Call to Action with Courtney Moran

The Future of Hemp in Oregon: A Call to Action with Courtney Moran

In this important conversation, Justin Botillier, CEO of Calyx CPA, sits down with Courtney Moran of Earth Law LLC to discuss the recent OLCC public hearing regarding which hemp products will be allowed in Oregon’s OLCC-regulated cannabis marketplace. Courtney, a leading attorney in the hemp and cannabis industries, shares her concerns about the lack of engagement from the industry at the hearing, where only one comment was made despite critical discussions on proposed rule changes. With the public comment period still open, there’s a final opportunity for businesses and individuals to make their voices heard.

 

Urgent Deadline: September 27th for Public Comment

The public comment period ends on September 27th at 12:00 PM, so now is the time to act. You can submit your thoughts and feedback directly to the OLCC by emailing [email protected] before the deadline.

 

How to Shape Hemp Regulation

Watch this video to learn more about the proposed hemp rules, the importance of industry engagement, and how you can influence the future of hemp regulation in Oregon.

 

For more details, be sure to read Courtney’s blog post here: https://www.agriculturalhempsolutions.com/post/olcc-holds-public-hearing-on-proposed-hemp-rulemaking

The Cannabis Journey Back to the Supreme Court: A Conversation with Katie Scates, CPA, JD

The Cannabis Journey Back to the Supreme Court: A Conversation with Katie Scates, CPA, JD

The Cannabis Journey Back to the Supreme Court: A Conversation with Katie Scates, CPA, JD

Introducing Katie Scates and Her Unique Expertise

Join Justin Botillier, CEO of Calyx CPA, in a candid conversation with Katie Scates, CPA, JD, the newest member of the Calyx CPA team. With her extensive background in both law and accounting, and specialized knowledge of the cannabis industry, Katie brings a unique perspective on navigating complex tax and legal challenges.

Key Developments in the Cannabis Industry

In this video, Justin and Katie explore the latest developments in the cannabis industry, focusing on the recent appellate brief challenging federal prohibition, as reported by Marijuana Moment.

Cannabis and the Legal Landscape

They discuss the implications of the case’s potential journey back to the Supreme Court, the future of 280E, and the rescheduling of cannabis under the Controlled Substances Act.

Insights for Cannabis Industry Professionals

Whether you’re in the cannabis space or curious about the legal landscape, this engaging discussion provides valuable insights into the future of cannabis regulation and taxation.

Oregon's Cannabis Certificate of Compliance: Insights from Attorney Kevin Jacoby

Navigating Oregon’s Cannabis Certificate of Compliance: Insights from Attorney Kevin Jacob

Navigating Oregon’s Certificate of Compliance Requirements for Cannabis Retailers

In this informative video, Kevin Jacoby, owner of Jacoby Law, shares valuable insights into Oregon’s Certificate of Compliance requirements for cannabis retailers. Oregon’s complex tax regulations present significant challenges for cannabis businesses, particularly when it comes to staying compliant with state-level taxes like marijuana sales tax, payroll taxes, and corporate income taxes. Kevin breaks down the specifics of the Certificate of Compliance, including who is required to file, what types of taxes are involved, and the often-overlooked requirement that even individual shareholders and partners must be personally compliant.

Challenges for Cannabis Businesses

Kevin and Justin Botillier, CEO of Calyx CPA, also discuss the controversial aspects of the law, such as the lack of legislative authority behind its implementation and the administrative burden it places on businesses. The conversation highlights how many cannabis operators are struggling to catch up on years of unfiled taxes and the importance of working with experienced professionals to avoid penalties and license issues.

Key Takeaways for Cannabis Retailers

Whether you’re a cannabis retailer in Oregon or simply interested in the intricacies of cannabis tax law, this discussion offers key takeaways on how to navigate the compliance process, potential rule changes, and the steps to take if you’re approaching compliance deadlines. Kevin also shares practical advice on extensions, dealing with the Oregon Liquor and Cannabis Commission (OLCC), and what to expect in the coming years as the state continues to refine its tax requirements for cannabis businesses.