ALPHA-PHENYL-BETA-(3,4-DIMETHOXY)PHENETHYLAMINES - NOVEL INHIBITORS OF CHOLINE-ACETYLTRANSFERASE FROM TORPEDO ELECTRIC ORGAN

Some derivatives [.alpha.-phenyl-.beta.-(3,4-dimethyoxy)phenethylamine, N-formyl-.alpha.-phenyl-.beta.-(3,4-dimethoxy)phenethylamine, N-ethoxycarbonyl-.alpha.-phenyl-.beta.-(3,4-dimethoxy)phenethylamine, N-methyl-.alpha.-phenyl-.beta.-(3,4-dimethoxy)phenethylamine hydrochloride and N,N-dimethyl-.alpha.-phenyl-.beta.-(3,4-dimethoxy)phenethylamine hydrochloride] of .alpha.-phenyl-.beta.-(3,4-dimethoxy)phenethylamine that might bear a certain conformational resemblance to choline were prepared. The in vitro inhibition of choline acetyltransferase from Torpedo electric organ was investigated. These compounds gave variable degrees of inhibition; the most potent inhibitor was, N,N,N-trimethyl-.alpha.-phenyl-.beta.-(3,4-dimethoxy)phenethylammonium iodide, with an I50 [median inhibitory concentration] of 1.3 .times. 10-5 M. The inhibition of choline acetyltransferase from Spodoptera littoralis larval brains was also determined for comparative study. The aforementioned compound has an I50 of 9 .times. 10-6 M on choline acetyltransferase from this source. [Few potent inhibitors of choline acetyltransferase are known, and those that have been tested have not proved useful as insecticides.].