Delta-10-Tetrahydrocannabinol

Delta-10-Tetrahydrocannabinol (Delta-10-THC, Δ10-THC, alternatively numbered as Δ2-THC) is an isomer of tetrahydrocannabinol, discovered in the 1980s. Two enantiomers have been reported in the literature, with the 9-methyl group in either the (R) or (S) conformation; of these the (R) enantiomer appears to be the more active isomer with about 30 to 40 percent the potency of delta-9-THC.[1][2][3] Δ10-THC has rarely been reported as a trace component of natural cannabis, though is thought to be a degradation product similar to cannabinol rather than being produced by the plant directly, however it is found more commonly as an impurity in synthetic delta-8-THC produced from cannabidiol,[4][5][6] and can also be synthesised directly from delta-9-THC.[7]

Delta-10-Tetrahydrocannabinol
Identifiers
IUPAC name
  • 6,6,9-trimethyl-3-pentyl-6a,7,8,9-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCC1=CC(=C2C3=CC(CCC3C(OC2=C1)(C)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/h11-14,17,22H,5-10H2,1-4H3
  • Key:YLTWYAXWDLZZCU-UHFFFAOYSA-N

See also

References
  1. 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.
  2. Järbe TU, Hiltunen AJ, Mechoulam R, Srebnik M, Breuer A (November 1988). "Separation of the discriminative stimulus effects of stereoisomers of delta 2- and delta 3-tetrahydrocannabinols in pigeons". European Journal of Pharmacology. 156 (3): 361–6. doi:10.1016/0014-2999(88)90281-6. PMID 2850933.
  3. WHO Expert Committee on Drug Dependence Critical Review. Isomers of THC (PDF) (Report). World Health Organization. 2018.
  4. Hanuš LO, Meyer SM, Muñoz E, Taglialatela-Scafati O, Appendino G (November 2016). "Phytocannabinoids: a unified critical inventory". Natural Product Reports. 33 (12): 1357–1392. doi:10.1039/c6np00074f. PMID 27722705.
  5. Chan-Hosokawa A, Nguyen L, Lattanzio N, Adams WR (March 2021). "Emergence of Delta-8 Tetrahydrocannabinol (THC) in DUID Investigation Casework: Method Development, Validation and Application". Journal of Analytical Toxicology. doi:10.1093/jat/bkab029. PMID 33754645.
  6. Erickson BE. Delta-8-THC craze concerns chemists. Chemical & Engineering News, 30 August 2021
  7. WO 2020248059, Adair C, Geiling B, Haghdoost Manjili M., "Methods for preparing cannabinoids by base-promoted double-bond migration.", published 2020-12-17, assigned to Canopy Growth Corporation
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