Abstract
A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7alpha-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with some selectivity for the mu opioid receptor, with evidence of micro efficacy in vivo. The similarity in SAR between these 6,14-bridged oripavines and the 14-cinnamoylamino series suggests a similar mode of interaction with the micro opioid receptor.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Analgesics / chemical synthesis*
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Analgesics / pharmacology
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Animals
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Binding, Competitive
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CHO Cells
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Cinnamates / chemical synthesis*
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Cinnamates / pharmacology
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Cricetinae
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Cricetulus
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Humans
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Ligands
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Mice
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Molecular Conformation
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Narcotic Antagonists*
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Radioligand Assay
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Receptors, Opioid / agonists*
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Receptors, Opioid, delta / agonists
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Receptors, Opioid, delta / antagonists & inhibitors
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Receptors, Opioid, kappa / agonists
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Receptors, Opioid, kappa / antagonists & inhibitors
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Receptors, Opioid, mu / agonists
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Receptors, Opioid, mu / antagonists & inhibitors
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Structure-Activity Relationship
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Thebaine / analogs & derivatives*
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Thebaine / chemical synthesis
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Thebaine / pharmacology
Substances
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7-aminomethyl-6,14-ethanotetrahydrooripavine
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7-aminomethyl-6,14-ethanotetrahydrothebaine
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Analgesics
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Cinnamates
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Ligands
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Narcotic Antagonists
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Receptors, Opioid
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Receptors, Opioid, delta
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Receptors, Opioid, kappa
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Receptors, Opioid, mu
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Thebaine
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oripavine