Cannabimimetic Activity of Novel Enantiomeric, Benzofuran Cannabinoids

Raphael Mechoulam, Aviva Breuer, Tobjorn U.C. Järbe, Arto J. Hiltunen, Robert Glaser

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

The synthesis of the (2R,3R,4S,6R)-7/(2S,3S,4R,6S)-8 enantiomeric pair of benzofuran cannabinoids is reported together with the 1H and 13C NMR spectral parameters. In benzofuran 8 the configurational arrangement of ligated groups at the stereogenic C(3) atom (through which the terpene moiety is connected to the aromatic ring) is very similar to that of the corresponding atom in natural (3R,4R)-Δ1tetrahydrocannabinol (Δ1THC), although their respective Cahn-Ingold-Prelog descriptors are different. In drug-discrimination tests in pigeons and rats, benzofuran 8 is as active as Δ1-THC; in the mouse ring test compound 8 is more active than Δ6-THC. Enantiomer 7 is considerably less active than enantiomer 8 in both tests. These results can be explained by the fact that both 7 and 8 have a dimethylheptyl side chain (which is known to enhance cannabimimetic activity) and that Δ1-THC and benzofuran 8 have closely related conformations, as determined by molecular mechanics.

Original languageEnglish
Pages (from-to)1037-1043
Number of pages7
JournalJournal of Medicinal Chemistry
Volume33
Issue number3
DOIs
StatePublished - 1 Jan 1990

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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