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Δ-11-Tetrahydrocannabinol

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(Redirected from Exo-THC) Isomer of tetrahydrocannabinol

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-Δ-8-THC. Pharmaceutical compound
Δ-11-Tetrahydrocannabinol
Identifiers
IUPAC name
  • (6aR,10aR)-6,6-dimethyl-9-methylidene-3-pentyl-7,8,10,10a-tetrahydro-6aH-benzochromen-1-ol
CAS Number
PubChem CID
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol
3D model (JSmol)
SMILES
  • CCCCCC1=CC(=C23CC(=C)CC3C(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/h12-13,16-17,22H,2,5-11H2,1,3-4H3/t16-,17-/m1/s1
  • Key:AOYYFUGUUIRBML-IAGOWNOFSA-N

Δ-11-Tetrahydrocannabinol (Delta-11-THC, Δ-THC, Δ-THC, exo-Tetrahydrocannabinol) is a rare isomer of tetrahydrocannabinol, developed in the 1970s. It can be synthesised from Δ-THC by several different routes, though only the (6aR, 10aR) enantiomer is known. In recent studies in 2022 it was found to "significantly reduce" the effects of Δ-THC and has been suggested as antagonist of the CB1 receptor in humans, with the cited study showing "one partial success in the quest for an antagonist is the fact that D9,11-THC was found to significantly reduce the effect of D9-THC." and did not substitute for THC in rhesus monkeys. It has been identified as a component of grey market vaping liquids sold for use in humans.

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. 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.
  6. 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.
  7. WHO Expert Committee on Drug Dependence Critical Review. Isomers of THC (PDF) (Report). World Health Organization. 2018.
  8. 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. Bibcode:2021FrCh....9..726C. doi:10.3389/fchem.2021.746479. PMC 8499677. PMID 34631667.
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