Chemistry:Cis-THC

From HandWiki
Short description: Cis enantiomer of tetrahydrocannabidiol

Cis-THC
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)

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. Formation of cis-THC could take place in process of epimerization associated with acid-catalyzed cyclization of CBD to THC.[1] 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.[2][3][4][5][6][7][8][9]

A diagram showing the isomers of delta-9-THC with carbon number indicated according to dibenzopyran numbering scheme. Cahn-Ingold-Prelog R/S designation is indicated. Please note that "synthetic" here refers to macroscopic quantities, and that these stereoisomers that are labeled as synthetic may be present in C. sativa or other organisms at trace levels compared to trans-(-)-d9-THC

See also

References

  1. ↑ "Acid-Catalyzed Conversion of Cannabidiol to Tetrahydrocannabinols: En Route to Demystifying Manufacturing Processes and Controlling the Reaction Outcomes" (in en). Cannabis and Cannabinoid Research 10 (3): 377–388. 2025-06-01. doi:10.1089/can.2025.0015. ISSN 2578-5125. PMID 40250991. https://www.liebertpub.com/doi/10.1089/can.2025.0015. 
  2. ↑ "Hashish. Importance of the phenolic hydroxyl group in tetrahydrocannabinols". Journal of Medicinal Chemistry 18 (2): 213–215. February 1975. doi:10.1021/jm00236a025. PMID 1120991. 
  3. ↑ "Δ1-3, 4-cis-tetrahydrocannabinol in Cannabis sativa.". Phytochemistry 16 (7): 1088–1089. January 1977. doi:10.1016/S0031-9422(00)86745-X. Bibcode: 1977PChem..16.1088S. 
  4. ↑ "Synthetic tetrahydrocannabinol". Journal of Forensic Sciences 28 (3): 762–772. July 1983. doi:10.1520/JFS11571J. PMID 6311937. 
  5. ↑ "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. doi:10.1021/jo9005365. PMID 19402693. 
  6. ↑ "High-pressure access to the Δ9-cis- and Δ9-trans-tetrahydrocannabinols family". The Journal of Organic Chemistry 76 (13): 5392–5403. July 2011. doi:10.1021/jo200796b. PMID 21563759. 
  7. ↑ "Stereodivergent total synthesis of Δ9-tetrahydrocannabinols". Angewandte Chemie (International Ed. in English) 53 (50): 13898–13901. December 2014. doi:10.1002/anie.201408380. PMID 25303495. 
  8. ↑ "Δ9-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology". Journal of Natural Products 84 (9): 2502–2510. September 2021. doi:10.1021/acs.jnatprod.1c00513. PMID 34304557. https://boris.unibe.ch/161548/. 
  9. ↑ "Brønsted Acid Catalyzed Asymmetric Synthesis of cis-Tetrahydrocannabinoids". Angewandte Chemie (International Ed. in English) 62 (24). April 2023. doi:10.1002/anie.202302475. PMID 37057742. 




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