Δ-11-Tetrahydrocannabinol
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| Other names | Delta-11-THC, Exo-THC, Δ11-THC, Δ9(11)-THC, exo-Tetrahydrocannabinol |
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| Formula | C21H30O2 |
| Molar mass | 314.469 g·mol−1 |
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Δ-11-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][5] and did not substitute for Δ9-THC in rhesus monkeys.[6][7] It has been identified as a component of grey market vaping liquids sold for use in humans.[8] Δ11-THC has been identified as an impurity found in pharmaceutical dronabinol.[9][10]
See also
[edit]- Abeo-HHC acetate
- Cis-THC
- Δ-3-Tetrahydrocannabinol
- Δ-4-Tetrahydrocannabinol
- Δ-7-Tetrahydrocannabinol
- Δ-10-Tetrahydrocannabinol
- Hexahydrocannabinol
- Iso-THC
- L-759,656
References
[edit]- ^ Wildes JW, Martin NH, Pitt CG, Wall ME (March 1971). "The synthesis of (-)-delta-9(11)-trans-tetrahydrocannabinol". The Journal of Organic Chemistry. 36 (5): 721–723. doi:10.1021/jo00804a024. PMID 5545571.
- ^ Banijamali AR, Makriyannis A (1998). "Novel synthesis of (−)-trans-Δ9,11-tetrahydrocannabinol". Journal of Heterocyclic Chemistry. 25 (3): 823–825. doi:10.1002/jhet.5570250324.
- ^ Banijamali AR, Van Der Schyf CJ, Makriyannis A (1998). "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. doi:10.1002/(SICI)1099-1344(199802)41:2<121::AID-JLCR55>3.0.CO;2-S.
- ^ Compton DR, Prescott WR, Martin BR, Siegel C, Gordon PM, Razdan RK (November 1991). "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. doi:10.1021/jm00115a023. PMID 1659638.
- ^ Compton DR, Prescott WR, Martin BR, Siegel C, Gordon PM, Razdan RK (November 1991). "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. doi:10.1021/jm00115a023. PMID 1659638.
- ^ Beardsley PM, Scimeca JA, Martin BR (May 1987). "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. PMID 3033218.
- ^ WHO Expert Committee on Drug Dependence Critical Review. Isomers of THC (PDF) (Report). World Health Organization. 2018.
- ^ Ciolino LA, Ranieri TL, Brueggemeyer JL, Taylor AM, Mohrhaus AS (2021). "EVALI Vaping Liquids Part 1: GC-MS Cannabinoids Profiles and Identification of Unnatural THC Isomers". Frontiers in Chemistry. 9: 746479. Bibcode:2021FrCh....9..726C. doi:10.3389/fchem.2021.746479. PMC 8499677. PMID 34631667.
- ^ https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/205525Orig1s000PharmR.pdf
- ^ https://www.cerilliant.com/shoponline/OpenDocument.aspx?DocumentID=38
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