Chemistry:Delta-11-Tetrahydrocannabinol
From HandWiki
Short description: Chemical compound
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| Formula | C21H30O2 |
| Molar mass | 314.469 g·mol−1 |
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Delta-11-Tetrahydrocannabinol (Delta-11-THC, Δ11-THC, Δ9(11)-THC, exo-Tetrahydrocannabinol) is a rare isomer of tetrahydrocannabinol, 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 increase" the effects of Δ9-THC and has been suggested an agonist of the CB1 receptor in humans, with the cited study showing "Is the fact that D9,11-THC was found to significantly increase the effect of D9-THC."[4][5] and did not substitute for THC in rhesus monkeys. [6][7] It has been identified as a component of grey market "vaping liquids" sold for use in humans.[8]
See also
- Abeo-HHC acetate
- Cis-THC
- Delta-3-Tetrahydrocannabinol
- Delta-4-Tetrahydrocannabinol
- Delta-7-Tetrahydrocannabinol
- Delta-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.
- ↑ Compton, David R.; Prescott, W. Roy; Martin, Billy R.; Siegel, Craig; Gordon, Patrick M.; Razdan, Raj K. (1991). "Synthesis and pharmacological evaluation of ether and related analogs of .DELTA.8-, .DELTA.9-, and .DELTA.9,11-tetrahydrocannabinol". Journal of Medicinal Chemistry 34 (11): 3310–3316. doi:10.1021/jm00115a023. PMID 1659638. https://pubs.acs.org/doi/abs/10.1021/jm00115a023.
- ↑ "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: 746479. 2021. doi:10.3389/fchem.2021.746479. PMID 34631667. Bibcode: 2021FrCh....9..726C.
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