Abstract
A series of ring-constrained phenylpropyloxyethylamines, partial opioid structure analogs and derivatives of a previously studied sigma (σ) receptor ligand, was synthesized and evaluated at σ and opioid receptors for receptor selectivity. The results of this study identified several compounds with nanomolar affinity at both σ receptor subtypes. Compounds 6 and 9 had the highest selectivity for both σ receptor subtypes, compared to μ opioid receptors. In addition, compounds 6 and 9 significantly reduced the convulsive effects of cocaine in mice, which would be consistent with antagonism of σ receptors.
Keywords:
Antagonists; Opioid; Phenylpropyloxyethylaminesl; Sigma.
Copyright © 2013. Published by Elsevier Ltd.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Animals
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Cocaine / chemistry
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Cocaine / toxicity
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Convulsants / chemistry
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Convulsants / metabolism
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Convulsants / therapeutic use
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Cyclohexanols / chemistry*
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Cyclohexanols / metabolism
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Cyclohexanols / therapeutic use
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Ethylamines / chemistry*
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Ethylamines / metabolism
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Ethylamines / therapeutic use
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Mice
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Phenethylamines / chemistry*
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Phenethylamines / metabolism
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Phenethylamines / therapeutic use
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Propylamines / chemistry*
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Propylamines / metabolism
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Propylamines / therapeutic use
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Protein Binding
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Receptors, sigma / antagonists & inhibitors*
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Receptors, sigma / metabolism
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Seizures / chemically induced
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Seizures / drug therapy
Substances
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2-(methyl(3-phenylpropyl)amino)cyclohexanol
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2-(methyl(phenethyl)amino)cyclohexanol
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Convulsants
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Cyclohexanols
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Ethylamines
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Phenethylamines
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Propylamines
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Receptors, sigma
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Cocaine