Chemistry:Δ11-Tetrahydrocannabinol
 | |
| Clinical data | |
|---|---|
| Other names | Delta-11-THC, Exo-THC, Δ11-THC, Δ9(11)-THC, exo-Tetrahydrocannabinol |
| ATC code |
|
| Identifiers | |
| |
| CAS Number |
|
| PubChem CID | |
| Chemical and physical data | |
| Formula | C21H30O2 |
| Molar mass | 314.469 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
Δ11-Tetrahydrocannabinol (Delta-11-THC, exo-THC, Δ11-THC, Δ9(11)-THC, exo-Tetrahydrocannabinol) is a rare isomer of tetrahydrocannabinol (Δ9-THC), developed in the 1970s. It can be synthesised from Δ8-THC by several different routes,[1][2][3] though only the (6aR, 10aR) enantiomer is known.
In recent studies in 2022 it was found to "significantly reduce" the effects of Δ9-THC and has been suggested to act as a CB1 receptor antagonist in humans, with the cited study showing "one partial success in the quest for an antagonist is the fact that D9,11-THC was found to significantly reduce the effect of D9-THC"[4] and did not substitute for Δ9-THC in rhesus monkeys.[5][6] It has been identified as a component of grey market vaping liquids sold for use in humans.[7] Δ11-THC has been identified as an impurity found in pharmaceutical dronabinol.[8][9]
Legality
United States
As of now, Delta-11-THC is federally legal and uncontrolled, and faces no repercussions for possession unless in Arkansas or other states that prohibit intoxicating hemp-derived cannabinoids. However, Delta-11-THC, being an isomer and analogue of illicit Delta-9-THC means it can be persecuted under the Federal Analogue Act
Arkansas
As of June 25, 2025, the U.S. 8th Circuit Court of Appeals overturned a lower court's injunction, allowing Arkansas to enforce its ban on hemp-derived THC products, including Delta-11 THC. This ruling means that Act 629, which classifies Delta-8, Delta-9 (above 0.3%), and Delta-10 THC ("Psychoactive hemp-derived cannabinoids" as stated in Act 629) as Schedule VI controlled substances in the state, is now enforceable. Previously, sales of these products had been temporarily permitted due to the injunction.[10][11]
Japan
Delta-11-THC falls under general THC restriction in Japan and is illegal to possess or use.
See also
- Abeo-HHC acetate
- Cis-THC
- Δ-3-Tetrahydrocannabinol
- Δ-4-Tetrahydrocannabinol
- Δ-7-Tetrahydrocannabinol
- Δ-10-Tetrahydrocannabinol
- Hexahydrocannabinol
- Iso-THC
- L-759,656
References
- ↑ "The synthesis of (-)-delta-9(11)-trans-tetrahydrocannabinol". The Journal of Organic Chemistry 36 (5): 721–723. March 1971. doi:10.1021/jo00804a024. PMID 5545571.
- ↑ "Novel synthesis of (−)-trans-Δ9,11-tetrahydrocannabinol.". Journal of Heterocyclic Chemistry 25 (3): 823–825. 1998. doi:10.1002/jhet.5570250324.
- ↑ "Addition and elimination of HCl to tetrahydrocannabinol isomers. A method for the preparation of stereospecifically 2H-labeled cannabinoids.". Journal of Labelled Compounds and Radiopharmaceuticals 41 (2): 121–130. 1998. doi:10.1002/(SICI)1099-1344(199802)41:2<121::AID-JLCR55>3.0.CO;2-S.
- ↑ "Synthesis and pharmacological evaluation of ether and related analogues of delta 8-, delta 9-, and delta 9,11-tetrahydrocannabinol". Journal of Medicinal Chemistry 34 (11): 3310–3316. November 1991. doi:10.1021/jm00115a023. PMID 1659638.
- ↑ "Studies on the agonistic activity of delta 9-11-tetrahydrocannabinol in mice, dogs and rhesus monkeys and its interactions with delta 9-tetrahydrocannabinol". The Journal of Pharmacology and Experimental Therapeutics 241 (2): 521–526. May 1987. PMID 3033218.
- ↑ WHO Expert Committee on Drug Dependence Critical Review. Isomers of THC. (Report). World Health Organization. 2018. https://cdn.who.int/media/docs/default-source/controlled-substances/isomersthc.pdf.
- ↑ "EVALI Vaping Liquids Part 1: GC-MS Cannabinoids Profiles and Identification of Unnatural THC Isomers". Frontiers in Chemistry 9. 2021. doi:10.3389/fchem.2021.746479. PMID 34631667. Bibcode: 2021FrCh....9..726C.
- ↑ [1] fda.gov]
- ↑ https://www.cerilliant.com/shoponline/OpenDocument.aspx?DocumentID=38
- ↑ Campbell, Matt (2025-06-24). "Federal court allows state to resume ban on sale of hemp-derived THC products" (in en-US). http://arktimes.com/arkansas-blog/2025/06/24/federal-court-allows-state-to-resume-ban-on-sale-of-hemp-derived-thc-products.
- ↑ Mobley, Matthew Sewell | Andrew (2025-06-24). "Arkansas to ban Delta-8, other THC products after appeals court victory" (in en). https://katv.com/news/local/court-upholds-arkansas-ban-on-psychoactive-hemp-products-ag-griffin-hails-decision-delta-8delta-9-recreational-marijuana-farm-bill-lawsuit.
 |  |
