Δ-3-Tetrahydrocannabinol
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| Formula | C21H30O2 |
| Molar mass | 314.469 g·mol−1 |
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Δ-3-Tetrahydrocannabinol (Delta-3-THC, Δ3-THC, Δ6a(10a)-THC, EA-1477) is a synthetic isomer of tetrahydrocannabinol, developed during the original research in the 1940s to develop synthetic routes to the natural products Δ8-THC and Δ9-THC found in the cannabis plant.[1] While the normal trans configuration of THC is in this case flattened by the double bond, it still has two enantiomers as the 9-methyl group can exist in an (R) or (S) conformation. The (S) enantiomer has similar effects to Δ9-THC though with several times lower potency, while the (R) enantiomer is many times less active or inactive, depending on the assay used.[2][3][4] It has been identified as a component of vaping liquid products.[5]
See also
[edit]- 7,8-Dihydrocannabinol
- Cannabitriol
- Delta-4-Tetrahydrocannabinol
- Delta-7-Tetrahydrocannabinol
- Delta-10-Tetrahydrocannabinol
- Hexahydrocannabinol
- JWH-138
- Parahexyl
References
[edit]- ^ US 2419935, Adams R, "Marihuana active compounds.", issued 1947
- ^ Matsumoto K, Stark P, Meister RG (January 1977). "Cannabinoids. 1. 1-Amino- and 1-mercapto-7,8,9,10-tetrahydro-6H-dibenzo [b,d]pyrans". Journal of Medicinal Chemistry. 20 (1): 17–24. doi:10.1021/jm00211a004. PMID 833820.
- ^ Consroe P, Martin AR, Fish BS (May 1982). "Use of a potential rabbit model for structure--behavioral activity studies of cannabinoids". Journal of Medicinal Chemistry. 25 (5): 596–9. doi:10.1021/jm00347a021. PMID 7086846.
- ^ Srebnik M, Lander N, Breuer A, Mechoulam R (1984). "Base-catalysed double-bond isomerizations of cannabinoids: structural and stereochemical aspects". Journal of the Chemical Society, Perkin Transactions 1: 2881–6. doi:10.1039/P19840002881.
- ^ 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.
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