Mode of action of local anesthetics. 4. Correlation between lipid solubility and biological activity of diastereomeric N-[N-dimethylphenylalanyl]ephedrine. Detection of asymmetric membrane structures as the site of action of local anesthetics

Abstract

No correlation existed between the lipid soly., basicity, or water soly. of diastereomeric N-(N,N-dimethylphenylalanyl)ephedrine (I) [37102-67-3] and its local anesthetic action. The stereoisomer, N-(L-N,N-dimethylphenylalanyl)-L-pseudoephedrine [14645-40-0] showed the highest lipid soly. but the least anesthetic action. This lack of correlation between lipid soly. and anesthetic action indicated that the site for anesthetic effects on the membrane was probably protein in nature.