Stereochemical requirements for cannabinoid activity.

R Mechoulam; N Lander; T H Varkony; I Kimmel; O Becker; Z Ben-Zvi; H Edery; G Porath

doi:10.1021/jm00184a002

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Stereochemical requirements for cannabinoid activity.

R Mechoulam·N Lander·T H Varkony·I Kimmel·O Becker·Z Ben-Zvi·H Edery·G Porath

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Abstract

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.

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Animals Cannabinoids Macaca mulatta Molecular Conformation Psychotropic Drugs Stereoisomerism Structure-Activity Relationship Journal Article Research Support, U.S. Gov't, P.H.S.

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R Mechoulam, N Lander, T H Varkony, I Kimmel, O Becker, Z Ben-Zvi, H Edery, G Porath. 1980. Stereochemical requirements for cannabinoid activity.. https://doi.org/10.1021/jm00184a002

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