Parasympatholytic (anticholinergic) esters of the isomeric 2-tropanols. 1. Glycolates

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Abstract
The 38 esters were prepared from the 4 isomeric 2-tropanols and a variety of racemic glycolic acids and their optical isomers. Anticholinergic activity in mice was measured in the peripheral nervous system (mydriasis) and in the CNS (anti-tremorine) and compared with that of atropine, scopolamine and dl-2-quinuclidinyl benzilate. Several esters had significantly greater activity in both the peripheral and CNS than did the reference compounds. Esters of (+)-2.alpha.-tropanol were more potent than those of either its epimer (-)-2.beta.-tropanol or its optical isomer (-)-2.alpha.-tropanol. Esters derived from (-)-glycolic acids were uniformly more potent than those from the (+)-glycolic acids. Esters of (+)-2.alpha.-nortropanol and 5 of its N-substituted derivatives had markedly decreased activity. Peripheral/central activity ratios and time-activity profiles for 5 active compounds are discussed and compared with those of the reference compounds.

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