Curare-Like Activity of Mono-Quaternary Salts Containing Adamantyl Residue at the Nitrogen Atom
ARMY FOREIGN SCIENCE AND TECHNOLOGY CENTER CHARLOTTESVILLE VA
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As shown in previous works, mono-quaternary salts of alkamine esters of benzoic and cinnamic acids types and exhibit a pronounced curare like action. A series of methiodides of alkamine esters of benzoic and cinnamic acids were synthesized, containing at the quaternary nitrogen atom a 1-adamantyl residue. The results of the analysis and the constants of the synthesized compounds are presented. The substitution of an N-methyl residue by an N-adamantyl causes a change of the substances mechanism of action, this applying both to the benzoic acid derivatives and to the cinnamic acid derivatives. In all cases, trimethylammonium compounds induce a spastic paralysis in chicks typical for depolarizing agents, at the same time that their adamantyl analogs induced a flaccid paralysis characteristic for a nondepolarzing block.
- Organic Chemistry