Delta-3-Tetrahydrocannabinol

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]

Delta-3-Tetrahydrocannabinol
Identifiers
IUPAC name
  • (9S)-6,6,9-trimethyl-3-pentyl-7,8,9,10-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCC1=CC(=C2C3=C(CC[C@@H](C3)C)C(OC2=C1)(C)C)O
InChI
  • 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/h12-14,22H,5-11H2,1-4H3/t14-/m0/s1
  • Key:NEBZNJDFIPBXCS-AWEZNQCLSA-N

See also

References
  1. US 2419935, Adams R, "Marihuana active compounds.", issued 1947
  2. Matsumoto K, Stark P, Meister RG (January 1977). "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. doi:10.1021/jm00211a004. PMID 833820.
  3. Consroe P, Martin AR, Fish BS (May 1982). "Use of a potential rabbit model for structure--behavioral activity studies of cannabinoids". Journal of Medicinal Chemistry. 25 (5): 596–9. doi:10.1021/jm00347a021. PMID 7086846.
  4. Srebnik M, Lander N, Breuer A, Mechoulam R (1984). "Base-catalysed double-bond isomerizations of cannabinoids: structural and stereochemical aspects". Journal of the Chemical Society, Perkin Transactions 1: 2881–6. doi:10.1039/P19840002881.
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