Abstract
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.
MeSH terms
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Adenylyl Cyclases / metabolism
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Analgesics, Opioid / chemical synthesis*
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Analgesics, Opioid / metabolism
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Analgesics, Opioid / pharmacology
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Animals
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Benzomorphans / analogs & derivatives
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Benzomorphans / chemical synthesis*
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Benzomorphans / metabolism
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Benzomorphans / pharmacology
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Brain / metabolism
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Cyclazocine / analogs & derivatives
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Depression, Chemical
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In Vitro Techniques
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Male
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Mice
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Morphinans / chemical synthesis*
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Neoplasms, Experimental / enzymology
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Neuroblastoma / enzymology
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Norepinephrine / metabolism
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Protein Binding / drug effects
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Rats
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Receptors, Opioid / drug effects*
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Receptors, Opioid / metabolism
Substances
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Analgesics, Opioid
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Benzomorphans
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Morphinans
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Receptors, Opioid
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normetazocine
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N-(2,4,5-trihydroxyphenethyl)normetazocine
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Adenylyl Cyclases
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Cyclazocine
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Norepinephrine