Cis-THC

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]

Clockwise from top left: "Natural" Δ9-THC, Unnatural Δ9-THC, (+)-cis-Δ9-THC and (-)-cis-Δ9-THC
Cis-THC
Identifiers
  • (6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
  • CCCCCC1=CC(=C2[C@@H]3C=C(CC[C@@H]3C(OC2=C1)(C)C)C)O
  • InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17+/m1/s1
  • Key:CYQFCXCEBYINGO-SJORKVTESA-N

See also

References
  1. Uliss DB, Dalzell HC, Handrick GR, Howes JF, Razdan RK (February 1975). "Hashish. Importance of the phenolic hydroxyl group in tetrahydrocannabinols". Journal of Medicinal Chemistry. 18 (2): 213–215. doi:10.1021/jm00236a025. PMID 1120991.
  2. Smith RM, Kempfert KD (January 1977). "Δ1-3, 4-cis-tetrahydrocannabinol in Cannabis sativa". Phytochemistry. 16 (7): 1088–1089. Bibcode:1977PChem..16.1088S. doi:10.1016/S0031-9422(00)86745-X.
  3. Churchill KT (July 1983). "Synthetic tetrahydrocannabinol". Journal of Forensic Sciences. 28 (3): 762–772. doi:10.1520/JFS11571J. PMID 6311937.
  4. Ballerini E, Minuti L, Piermatti O, Pizzo F (June 2009). "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. doi:10.1021/jo9005365. PMID 19402693.
  5. Minuti L, Ballerini E (July 2011). "High-pressure access to the Δ9-cis- and Δ9-trans-tetrahydrocannabinols family". The Journal of Organic Chemistry. 76 (13): 5392–5403. doi:10.1021/jo200796b. PMID 21563759.
  6. Schafroth MA, Zuccarello G, Krautwald S, Sarlah D, Carreira EM (December 2014). "Stereodivergent total synthesis of Δ9-tetrahydrocannabinols". Angewandte Chemie. 53 (50): 13898–13901. doi:10.1002/anie.201408380. PMID 25303495.
  7. Schafroth MA, Mazzoccanti G, Reynoso-Moreno I, Erni R, Pollastro F, Caprioglio D, et al. (September 2021). "Δ9-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology". Journal of Natural Products. 84 (9): 2502–2510. doi:10.1021/acs.jnatprod.1c00513. PMID 34304557. S2CID 236431636.
  8. Dorsch C, Schneider C (April 2023). "Brønsted Acid Catalyzed Asymmetric Synthesis of cis-Tetrahydrocannabinoids". Angewandte Chemie. 62 (24): e202302475. doi:10.1002/anie.202302475. PMID 37057742. S2CID 258135845.
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