Hashish. Importance of the phenolic hydroxyl group in tetrahydrocannabinols.
Optically active delta-3- and delta-8-tetrahydrocannabinols (THC's), cannabidiol and racemic delta-9-cis-THC, and their corresponding analogs (1b yields 4b) in which the positions of the phenolic hydroxyl group and the n-C5 side chain have been interchanged are compared in selected pharmacological tests in mice. the results indicate that the phenolic hydroxyl group in the 1 position in THC's is very important for eliciting activity and that cannabidiol and delta-9-cis-THC possess weak CNS depressant properties.
D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects; D002188:Cannabis / Q000494:pharmacology*; D013759:Dronabinol / Q000494:pharmacology* / Q000633:toxicity; D007928:Lethal Dose 50; D008297:Male; D051379:Mice; D008815:Mice, Inbred Strains; D009043:Motor Activity / Q000187:drug effects; D010433:Pentylenetetrazole / Q000037:antagonists & inhibitors; D010636:Phenols / Q000494:pharmacology*; D011930:Reaction Time / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014110:Touch
D010636:Phenols; D013759:Dronabinol; D010433:Pentylenetetrazole