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Bioorg Med Chem. 2010 Dec 1;18(23):8356-64. doi: 10.1016/j.bmc.2010.09.060. Epub 2010 Sep 29.

Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands.

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  • 1Department of Chemistry, University of New Orleans, LA 70148, USA.

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.

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