A novel probe for the cannabinoid receptor.
W A Devane, Aviva Breuer, T Sheskin, Torbjörn U C Järbe, M S Eisen, Raphael Mechoulam
Journal of Medicinal Chemistry May 29, 1992 DOI: 10.1021/jm00089a018 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Preclinical pharmacology and chemistry study Peer reviewed |
|---|---|
| Population | Pigeons (drug discrimination) and cannabinoid receptor binding assays |
| Interventions | 5'-(1 CP-55940 |
| Measures | ED50 (drug discrimination in pigeons), KD, Ki |
| Key points | The hydrogenated epimer compound 7 matches the parent DMH-THC analogue's potency in pigeon drug discrimination (ED50 = 0.002 mg/kg after 4.5 h) and binds the cannabinoid receptor with a KD of 45 pM, which the authors report is lower than the parent's 180 pM Ki and CP-55940's 2.0 nM Ki. Tritiated 7 is proposed as a novel receptor probe. |
Abstract
The 1,1-dimethylheptyl (DMH) homologue of 7-hydroxy-delta 6-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 delta 1-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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