Abstract
A series of benzyl esters of meperidine and normeperidine were synthesized and evaluated for binding affinity at serotonin, dopamine and norepinephrine transporters. The 4-methoxybenzyl ester 8b and 4-nitrobenzyl ester 8c in the meperidine series and 4-methoxybenzyl ester 14a in the normeperidine series exhibited low nanomolar binding affinities at the SERT (K(i) values <2nM) and high SERT selectivity (DAT/SERT >1500 and NET/SERT >1500).
Copyright © 2010 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Esters
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Ligands
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Meperidine / analogs & derivatives*
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Meperidine / chemical synthesis
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Meperidine / chemistry
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Meperidine / pharmacology
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Selective Serotonin Reuptake Inhibitors / chemical synthesis*
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Selective Serotonin Reuptake Inhibitors / chemistry
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Selective Serotonin Reuptake Inhibitors / pharmacology
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Serotonin Plasma Membrane Transport Proteins / chemistry*
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Serotonin Plasma Membrane Transport Proteins / metabolism
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Structure-Activity Relationship
Substances
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Esters
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Ligands
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Serotonin Plasma Membrane Transport Proteins
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Serotonin Uptake Inhibitors
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Meperidine
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normeperidine