1980/10/01 by Raphael Mechoulam, N. Lander, Tomas H. Varkony +5 · 62 citations
Chemistry · Medicine · #Analytical Chemistry and Chromatography #Biochemistry #Biological activity #Cannabinoid #Cannabis and Cannabinoid Research #Chemistry #In vitro #Molecular spectroscopy and chirality #Receptor #Stereochemistry #Substituent
paper · doi:10.1021/jm00184a002
published in Journal of Medicinal Chemistry 23(10), 1068-1072 (American Chemical Society)
openalex publication_date 1980/10/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/11
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.