Delta-11-Tetrahydrocannabinol

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 animal studies it was found to be active in mice with around 1/4 the potency of Δ9-THC,[4] but did not substitute for THC in rhesus monkeys, probably because the dose tested was not high enough to produce cannabinoid-like effects.[5][6] It has been identified as a component of "vaping liquids" sold for use in humans.[7]

This article is about a rare synthetic isomer of THC. For common isomers mistakenly referred to as "delta-11", see 11-Hydroxy-THC and 11-Hydroxy-Delta-8-THC.
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

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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