Stereochemical Requirements for Cannabinoid Activity

Article abstract of DOI:10.1021/jm00184a002

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.