Convulsant Activities of Aminocyclanol Derivatives as Influenced by Stereochemical Configurations.

Abstract

Generally, it has been found that cis and trans isomers of 1,2-tertiary amino-cyclanols and their esters, studied largely in the cyclohexane series, are capable of exhibiting convulsant activity in the mouse and the cat. From graded activities in the mouse it is observed that with few exceptions each cis isomer of a given cis-trans pair is more potent than its corresponding trans isomer. Within the tertiary-amino compounds as a class, it appears that convulsant activity in the mouse, which is roughly paralleled in the cat, runs in the increasing sequence alcohols< phenylacetate esters < diphenylacetate esters < benzilate esters. The probability that active and relatively inactive members of a quaternary cis-trans pair (e.g., la and Ha) reach the same receptor [image] centers in the cat is indicated by the observation that IIa protects against the action of Ia. The quaternary cis and trans benzilates (Ib and IIb) appear to show strong species specificity, with high activity in mice (cis better than trans) and low activity in cats.