Synthesis and Biological Activity of 1-Chloromethyl- and 1-Dichloromethyl-3,3-Dialkyl-3,4-Dihydroisoquinolinium Chlorides

Abstract

1-Chloromethyl- and 1-dichloromethyl-3,3-dialkyl-3,4-dihydroisoquinolines were synthesized via cyclo-condensation of dialkylbenzylcarbinols with chloroacetonitrile or dichloroacetonitrile. Their hydrochlorides were tested for antiarrhythmic, anticonvulsant, and analgesic activity. Water-soluble 1-chloromethylisoquinoline hydrochlorides showed antiarrhythmic activity with a maximum antiarrhythmic index of 14.8. These same compounds were active against corazole-induced convulsions. 1-Dichloromethylisoquinolines had analgesic effects comparable with that of metamizole sodium.