Stereochemical requirements for cannabinoid activity.
Several pairs of cannabinoid isomers were synthesized and tested for psychotropic activity in rhesus monkeys. Two regularities were observed: (a) In the absence of the other substituents, the equatorial stereochemistry of the substituent at C-1 determines activity. (b) Two groups of THC-type cannabinoids which differ only in that the chemical groupings in one of them at C-1, C-2 are situated at C-1, C-6 in the other (but retain their stereochemistry) have almost equivalent psychotropic activity.
D000818:Animals; D002186:Cannabinoids / Q000138:chemical synthesis / Q000494:pharmacology*; D008253:Macaca mulatta; D008968:Molecular Conformation; D011619:Psychotropic Drugs / Q000138:chemical synthesis; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D002186:Cannabinoids; D011619:Psychotropic Drugs