Design and Synthesis of Hemicholiniums and Quarternary Ammonium Compounds with Relatively Great Differences Between the Effective and Lethal Doses
Technical rept. Dec 1963-Feb 1971
EDGEWOOD ARSENAL ABERDEEN PROVING GROUND MD
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Nine selected series of quaternary ammonium compounds were synthesized to study relationships between their chemical structures and their biological activities. A general structure is presented indicating certain common chemical features required to obtain potent hemicholiniums, lethal pyridinium compounds, and other pyridinium compounds with relatively great differences between the effective and lethal doses. A new hemicholinium compound more potent than the original hemicholinium HC-3 was obtained. General chemical characteristics regarding the compositions of the presynaptic active sites participating in cholinergic neuromuscular impulse transmission are postulated. Possible mechanisms of action of ortho- and meta-pyridinium compounds meeting specific structural requirements are proposed.