A Novel Probe for the Cannabinoid Receptor

William A. Devane*, Aviva Breuer, Tzviel Sheskin, Torbjörn U.C. Järbe, Moris S. Eisen, Raphael Mechoulam, Torbjörn U.C. Järbe

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

160 Scopus citations


The 1,1-dimethylheptyl (DMH) homologue of 7-hydroxy-Δ6-tetrahydrocannabinol (3) is the most potent cannabimimetic substance reported so far. Hydrogenation of 3 leads to a mixture of the epimers of 5′-(1, 1-dimethylheptyl)-7-hydroxyhexahydrocannabinol or to either the equatorial (7) or to the axial epimer (8), depending on the catalysts and conditions used. Compound 7 discriminates for Δ1-THC (2) in pigeons (ED50 = 0.002 mg/kg, after 4.5 h), at the potency level of 3, and binds to the cannabinoid receptor with a KD of 45 pM, considerably lower than the Ki of 180 pM measured for compound 3 and the Ki of 2.0 nM measured for CP-55940 (1), a widely employed ligand. Tritiated 7 was used as a novel probe for the cannabinoid receptor.

Original languageEnglish
Pages (from-to)2065-2069
Number of pages5
JournalJournal of Medicinal Chemistry
Issue number11
StatePublished - 1 May 1992
Externally publishedYes


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