Oxidative and cardiovascular studies on natural and synthetic catecholamines

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Abstract
The cyclic voltammometric behavior of epinephrine, norepinephrine, dopamine, epinine, .alpha.-methyldopamine, .beta.-methyldopamine, .beta.-methylepinine and .beta.-methoxyepinephrine was examined to evaluate substituent effects on cyclization rates of the electrochemically generated quinones. .alpha. and .beta. substituents caused a modest enhancement of cyclization rates while an N-methyl group dramatically increased cyclization rates. No correlation was observed between calculated amine pKa values, suggesting that differences in cyclization rates between the primary and secondary amine series were due to inherent nucleophilicity, a measure of which would be gas-phase proton affinities. The acute pressor effects of the newly synthesized catecholamines were compared with the native amines.