Abstract
1. A series of alkyl, aryl, dialkyl and aryl-alkyl carbamic esters of phenols containing a basic substituent directly or indirectly attached to the phenyl radicle have been examined for physostigmine-like action, the toxicities, miotic action and effect on intestinal peristalsis being tabulated.
2. Several related compounds which do not contain both a carbamic ester group and a basic substituent show no activity.
3. The physostigmine-action is strong in methyl-, dimethyl-, allyl-, benzyl- and methylphenyl-carbamic esters of phenol-bases, weak in ethyl- and phenyl- and absent in diethyl and diallylcarbamic esters of this series. The esters of disubstituted carbamic acids are stable.
4. The quaternary salts of the aromatic bases were more active than the hydrochlorides of the corresponding tertiary bases. When the basic radicle was in the side chain the difference was less marked or reversed.
5. The dimethyl- and methylphenyl-carbamic esters of 3-oxyphenyl-trimethylammonium methylsulfate have been fully investigated. They are at least as active as physostigmine in stimulating intestinal peristalsis. The miotic activity of the dimethylcarbamic ester is similar to that of physostigmine, that of the methyl-phenyl-carbamic ester being weak. The latter does not show an antagonistic action to curare. The symptoms produced by toxic doses are similar to those produced by physostigmine.
Footnotes
- Received June 1, 1931.
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