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Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/20774
Title: Synthesis of the major metabolites of Paroxetine
Authors: Segura, Mireia; Roura, Lidia; Torre, Rafael de la; Joglar Tamargo, Jesús
Keywords: Paraxotine
Synthesis of paroxetine metabolites
Issue Date: 28-May-2003
Publisher: Elsevier
Citation: Bioorganic Chemistry 31(3): 284-258 (2003)
Abstract: Paroxetine is a well-known antidepressant, used worldwide in therapeutics. In comparison with other selective serotonin reuptake inhibitors, it exhibits the highest activity in serotonin reuptake inhibition. Paroxetine metabolism initially involves its demethylenation to the catechol intermediate, which is then O-methylated at positions C3 or C4. Herein, the chemistry resulting in the syntheses of these metabolites (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine and (3S,4R)-4-(4-fluorophenyl)-3-(4-hydroxy-3-methoxyphenoxymethyl)piperidine is described starting from the common intermediate (3S,4R)-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine. Additionally, the common intermediate was used to synthesize paroxetine, which had the same structure and stereochemistry as commercial paroxetine, thereby confirming our synthetic route.
Description: 11 pages, 3 figures.-- PMID: 12818234 [PubMed].-- Printed version published Jun 2003.
Publisher version (URL): http://dx.doi.org/10.1016/S0045-2068(03)00040-3
URI: http://hdl.handle.net/10261/20774
ISSN: 0045-2068 (Print)
DOI: 10.1016/S0045-2068(03)00040-3
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