N-(2,4,5-Trihydroxyphenethyl)normetazocine, a potential irreversible inhibitor of the narcotic receptor
作者:Kenner C. Rice、Shunsaku Shiotani、Cyrus R. Creveling、Arthur E. Jacobson、Werner A. Klee
DOI:10.1021/jm00215a011
日期:1977.5
The reaction of N-2,4,5-tribenzyloxyphenyl)ethyl methanesulfonate, prepared in a seven-step sequence, with normetazocine followed by hydrogenolysis of the benzyloxy-protecting groups, gave N-(2,4,5-trihydroxyphenethyl)normetazocine. This compound was prepared to study the effect of a narcotic analgesic containing a functional group which could be activated in situ to a moiety potentially capable of reacting irreversibly with the narcotic receptor. This 6-hydroxydopamin derivative of normetazocine did not prove to be a useful affinity label. Its low toxicity could indicate the necessity for the formation of an aminochrome system for the expression of toxicity by 6-hydroxydopamine.