Cis-THC explained

cis-Delta-9-Tetrahydrocannabinol ((-)-cis-Δ⁹-THC) is an isomer of tetrahydrocannabinol found in the Cannabis plant but in lower quantities than the more well-known trans isomer. It has similar psychoactive effects to trans-Δ⁹-THC in tests on mice, but with only around 1/5th the potency. The equivalent Δ⁸ isomer is also known as a synthetic compound, but has not been isolated from Cannabis plant material. All four cis/trans isomers are known, though only the (6aR,10aR) and (6aS,10aR) enantiomers are psychoactive, while the others retain activity at targets such as GPR18 and GPR55.^{[1] [2] [3] [4] [5] [6] [7] [8]}

See also

• Abeo-HHC acetate
• Abn-CBD
• CBD-DMH
• Exo-THC
• Iso-THC
• HU-211
• Perrottetinene
• Machaeriol A

Notes and References

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2. Smith RM, Kempfert KD . Δ1-3, 4-cis-tetrahydrocannabinol in Cannabis sativa. . Phytochemistry . January 1977 . 16 . 7 . 1088–1089 . 10.1016/S0031-9422(00)86745-X . 1977PChem..16.1088S .
3. Churchill KT . Synthetic tetrahydrocannabinol . Journal of Forensic Sciences . 28 . 3 . 762–772 . July 1983 . 10.1520/JFS11571J . 6311937 .
4. Ballerini E, Minuti L, Piermatti O, Pizzo F . High pressure Diels-Alder approach to hydroxy-substituted 6a-cyano-tetrahydro-6H-benzo[c]chromen-6-ones: a route to delta(6)-cis-cannabidiol . The Journal of Organic Chemistry . 74 . 11 . 4311–4317 . June 2009 . 19402693 . 10.1021/jo9005365 .
5. Minuti L, Ballerini E . High-pressure access to the Δ9-cis- and Δ9-trans-tetrahydrocannabinols family . The Journal of Organic Chemistry . 76 . 13 . 5392–5403 . July 2011 . 21563759 . 10.1021/jo200796b .
6. Schafroth MA, Zuccarello G, Krautwald S, Sarlah D, Carreira EM . Stereodivergent total synthesis of Δ9-tetrahydrocannabinols . Angewandte Chemie . 53 . 50 . 13898–13901 . December 2014 . 25303495 . 10.1002/anie.201408380 .
7. Schafroth MA, Mazzoccanti G, Reynoso-Moreno I, Erni R, Pollastro F, Caprioglio D, Botta B, Allegrone G, Grassi G, Chicca A, Gasparrini F, Gertsch J, Carreira EM, Appendino G . 6 . Δ⁹-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology . Journal of Natural Products . 84 . 9 . 2502–2510 . September 2021 . 34304557 . 10.1021/acs.jnatprod.1c00513 . 236431636 . 20.500.11850/508697 . free .
8. Dorsch C, Schneider C . Brønsted Acid Catalyzed Asymmetric Synthesis of cis-Tetrahydrocannabinoids . Angewandte Chemie . e202302475 . April 2023 . 62 . 24 . 37057742 . 10.1002/anie.202302475 . 258135845 . free .