Journal of Medicinal Chemistry p. 2065 - 2069 (1992)
Update date:2022-08-11
Topics:
Devane, William A.
Breuer, Aviva
Sheskin, Tzviel
Jaerbe, Torbjoern U. C.
Eisen, Moris S.
Mechoulam, Raphael
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.
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