Chemistry:Delta-3-Tetrahydrocannabinol

From HandWiki
Short description: Chemical compound
Delta-3-Tetrahydrocannabinol
Delta-3-THC Structure.svg
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)

Delta-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

References

  1. Adams R, "Marihuana active compounds.", US patent 2419935, issued 1947
  2. "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. doi:10.1021/jm00211a004. PMID 833820. 
  3. "Use of a potential rabbit model for structure--behavioral activity studies of cannabinoids". Journal of Medicinal Chemistry 25 (5): 596–9. May 1982. doi:10.1021/jm00347a021. PMID 7086846. 
  4. "Base-catalysed double-bond isomerizations of cannabinoids: structural and stereochemical aspects.". Journal of the Chemical Society, Perkin Transactions 1: 2881–6. 1984. doi:10.1039/P19840002881. 
  5. "EVALI Vaping Liquids Part 1: GC-MS Cannabinoids Profiles and Identification of Unnatural THC Isomers". Frontiers in Chemistry 9: 746479. 2021. doi:10.3389/fchem.2021.746479. PMID 34631667.