Abstract
The synthesis and sigma 1 and sigma 2 binding properties of several 1'- and 3'-halo- and 1',3'-dihalo-substituted analogues of (+)-N-benzyl- and (+)- and (-)-N-dimethylallyl-N-normetazocine are presented. Structure-activity relationship analyses of the binding data showed that halogen substitution at the 1'-position of these N-substituted N-normetazocine analogues had little effect on sigma 1 binding affinity, whereas 3'-halo substitution as well as 1',3'-dihalo substitution resulted in a reduction of affinity. sigma 2 affinity was increased by the presence of a 3'-bromo substituent in this series of (+)-N-substituted N-normetazocines.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Animals
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Cyclazocine / analogs & derivatives*
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Cyclazocine / chemical synthesis
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Cyclazocine / metabolism
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Cyclazocine / pharmacology
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Guinea Pigs
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Hydrocarbons, Halogenated / chemical synthesis*
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Hydrocarbons, Halogenated / metabolism
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Hydrocarbons, Halogenated / pharmacology*
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Narcotics / chemical synthesis*
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Narcotics / metabolism*
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Narcotics / pharmacology
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Pentazocine / analogs & derivatives
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Rats
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Receptors, sigma / drug effects
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Receptors, sigma / metabolism*
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Structure-Activity Relationship
Substances
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Hydrocarbons, Halogenated
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Narcotics
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Receptors, sigma
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normetazocine
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Cyclazocine
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Pentazocine