2-Methyl- and 4-methyl-δ8-tetrahydrocannabinol: Correlation of spatial distinction with cannabinoid receptor binding

Robert Glaser, Itay Adin, Raphael Mechoulam, Lumir Hanuš

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A high level of binding to the brain cannabinoid receptor was found for 2-methyl-Δ8-tetrahydrocannabinol (THC) while no binding was observed for 4-methyl-Δ8-THC. Four energy minima were found by molecular mechanics for ethyl side-chain models of Δ8-THC [syn- and antiperiplanar and (±)-orthogonal values for torsion angle C(4)-C(3)-C(α)-C(β)]. The active Δ8-THC and 2-methyl-Δ8-THC molecules share a common structural feature [a relatively low energy synperiplonar value C(4)-C(3)-C(α)-C(β) torsion angle conformation for the n-pentyl side chain] that is not exhibited by the inactive 4-methyl-Δ8-THC analogue. This spatial distinction may represent the basis for the difference in biological activity between the two isomers examined.

Original languageEnglish
Pages (from-to)867-877
Number of pages11
JournalHeterocycles
Volume39
Issue number2
DOIs
StatePublished - 31 Dec 1994

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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