Δ-3-Tetrahydrocannabinol Explained

Δ-3-Tetrahydrocannabinol (Delta-3-THC, Δ³-THC, Δ^6a(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

• 7,8-Dihydrocannabinol
• Cannabitriol
• Delta-4-Tetrahydrocannabinol
• Delta-7-Tetrahydrocannabinol
• Delta-10-Tetrahydrocannabinol
• Hexahydrocannabinol
• JWH-138
• Parahexyl

Notes and References

1. Marihuana active compounds. . Adams R . US . 2419935 . 1947 .
2. Matsumoto K, Stark P, Meister RG . 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 . January 1977 . 833820 . 10.1021/jm00211a004 .
3. Consroe P, Martin AR, Fish BS . Use of a potential rabbit model for structure--behavioral activity studies of cannabinoids . Journal of Medicinal Chemistry . 25 . 5 . 596–9 . May 1982 . 7086846 . 10.1021/jm00347a021 .
4. Srebnik M, Lander N, Breuer A, Mechoulam R . Base-catalysed double-bond isomerizations of cannabinoids: structural and stereochemical aspects. . Journal of the Chemical Society, Perkin Transactions 1 . 1984 . 2881–6 . 10.1039/P19840002881 .
5. Ciolino LA, Ranieri TL, Brueggemeyer JL, Taylor AM, Mohrhaus AS . EVALI Vaping Liquids Part 1: GC-MS Cannabinoids Profiles and Identification of Unnatural THC Isomers . Frontiers in Chemistry . 9 . 746479 . 2021 . 34631667 . 8499677 . 10.3389/fchem.2021.746479 . 2021FrCh....9..726C . free .