Delta-11-Tetrahydrocannabinol
Identifiers
  • (6aR,10aR)-6,6-dimethyl-9-methylidene-3-pentyl-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-1-ol
CAS Number
PubChem CID
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
  • CCCCCC1=CC(=C2[C@@H]3CC(=C)CC[C@H]3C(OC2=C1)(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/h12-13,16-17,22H,2,5-11H2,1,3-4H3/t16-,17-/m1/s1
  • Key:AOYYFUGUUIRBML-IAGOWNOFSA-N

Delta-11-Tetrahydrocannabinol (Delta-11-THC, Δ11-THC, Δ9(11)-THC, exo-Tetrahydrocannabinol) is a synthetic isomer of tetrahydrocannabinol, developed in the 1970s. It can be synthesised from Δ8-THC by several different routes,[1][2][3] though only the (6aR, 10aR) enantiomer is known. In recent studies in 2022 it was found "significantly reduce" the effects of Δ9-THC and has suggested to be an antagonist of the CB1 receptor,[4] and did not substitute for THC in rhesus monkeys. [5][6] It has been identified as a component of "vaping liquids" sold for use in humans.[7]

See also

References

  1. ↑ Wildes JW, Martin NH, Pitt CG, Wall ME (March 1971). "The synthesis of (-)-delta-9(11)-trans-tetrahydrocannabinol". The Journal of Organic Chemistry. 36 (5): 721–723. doi:10.1021/jo00804a024. PMID 5545571.
  2. ↑ Banijamali AR, Makriyannis A (1998). "Novel synthesis of (−)-trans-Δ9,11-tetrahydrocannabinol". Journal of Heterocyclic Chemistry. 25 (3): 823–825. doi:10.1002/jhet.5570250324.
  3. ↑ Banijamali AR, Van Der Schyf CJ, Makriyannis A (1998). "Addition and elimination of HCl to tetrahydrocannabinol isomers. A method for the preparation of stereospecifically 2H-labeled cannabinoids". Journal of Labelled Compounds and Radiopharmaceuticals. 41 (2): 121–130. doi:10.1002/(SICI)1099-1344(199802)41:2<121::AID-JLCR55>3.0.CO;2-S.
  4. ↑ Compton DR, Prescott WR, Martin BR, Siegel C, Gordon PM, Razdan RK (November 1991). "Synthesis and pharmacological evaluation of ether and related analogues of delta 8-, delta 9-, and delta 9,11-tetrahydrocannabinol". Journal of Medicinal Chemistry. 34 (11): 3310–3316. doi:10.1021/jm00115a023. PMID 1659638.
  5. ↑ Beardsley PM, Scimeca JA, Martin BR (May 1987). "Studies on the agonistic activity of delta 9-11-tetrahydrocannabinol in mice, dogs and rhesus monkeys and its interactions with delta 9-tetrahydrocannabinol". The Journal of Pharmacology and Experimental Therapeutics. 241 (2): 521–526. PMID 3033218.
  6. ↑ WHO Expert Committee on Drug Dependence Critical Review. Isomers of THC (PDF) (Report). World Health Organization. 2018.
  7. ↑ Ciolino LA, Ranieri TL, Brueggemeyer JL, Taylor AM, Mohrhaus AS (2021). "EVALI Vaping Liquids Part 1: GC-MS Cannabinoids Profiles and Identification of Unnatural THC Isomers". Frontiers in Chemistry. 9: 746479. doi:10.3389/fchem.2021.746479. PMC 8499677. PMID 34631667.
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