N-(2,4,5-Trihydroxyphenethyl)normetazocine, a potential irreversible inhibitor of the narcotic receptor

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Abstract
The reaction of N-(2,4,5-tribenzyloxyphenyl)ethyl methanesulfonate, prepared in a 7-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-hydroxydopamine derivative of normetazocine was not a useful affinity label. Its low toxicity [in mice] could indicate the necessity for the formation of an aminochrome system for the expression of toxicity by 6-hydroxydopamine.