N-(2,4,5-Trihydroxyphenehtyl)normetazocine, a potential irreversible inhibitor of the narcotic receptor.
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.
D000262:Adenylyl Cyclases / Q000378:metabolism; D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D000818:Animals; D001575:Benzomorphans / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D001921:Brain / Q000378:metabolism; D003496:Cyclazocine / Q000031:analogs & derivatives; D003864:Depression, Chemical; D066298:In Vitro Techniques; D008297:Male; D051379:Mice; D009019:Morphinans / Q000138:chemical synthesis*; D009374:Neoplasms, Experimental / Q000201:enzymology; D009447:Neuroblastoma / Q000201:enzymology; D009638:Norepinephrine / Q000378:metabolism; D011485:Protein Binding / Q000187:drug effects; D051381:Rats; D011957:Receptors, Opioid / Q000187:drug effects* / Q000378:metabolism
D000701:Analgesics, Opioid; D001575:Benzomorphans; D009019:Morphinans; D011957:Receptors, Opioid; C014716:normetazocine; C014869:N-(2,4,5-trihydroxyphenethyl)normetazocine; D000262:Adenylyl Cyclases; D003496:Cyclazocine; D009638:Norepinephrine