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Zusammenfassung
The 8 stereoisomers of N-[N-dimethylphenylalanyl]ephedrine [10385-91-8], the 2 stereoisomers of N-[N-dimethylalanyl]-2,6-dimethylaniline [19216-39-8] (I, R = H), and the 2 stereoisomers of N-[N-dimethylphenylalanyl]-2,6-dimethylaniline [19216-40-1] (I, R = Ph) were synthesized and tested, as models of local anesthetics, for their ability to slow the impulse conduction velocity of frog ventricle ...
Zusammenfassung
The 8 stereoisomers of N-[N-dimethylphenylalanyl]ephedrine [10385-91-8], the 2 stereoisomers of N-[N-dimethylalanyl]-2,6-dimethylaniline [19216-39-8] (I, R = H), and the 2 stereoisomers of N-[N-dimethylphenylalanyl]-2,6-dimethylaniline [19216-40-1] (I, R = Ph) were synthesized and tested, as models of local anesthetics, for their ability to slow the impulse conduction velocity of frog ventricle strips. In all cases, each enantiomeric pair had quant. different effects, supporting the concept that local anesthetics react in a stereospecific manner with structural proteins in the membranes, leading to a blockade of impulse conduction. A discussion of membrane structure and of the interaction of enantiomeric compds. with receptors is given.