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Título

Synthesis of the major metabolites of Paroxetine

AutorSegura, Mireia; Roura, Lidia; Torre, Rafael de la; Joglar Tamargo, Jesús
Palabras claveParaxotine
Synthesis of paroxetine metabolites
Antidepressant
Fecha de publicación28-may-2003
EditorElsevier
CitaciónBioorganic Chemistry 31(3): 284-258 (2003)
ResumenParoxetine 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.
Descripción11 pages, 3 figures.-- PMID: 12818234 [PubMed].-- Printed version published Jun 2003.
Versión del editorhttp://dx.doi.org/10.1016/S0045-2068(03)00040-3
URIhttp://hdl.handle.net/10261/20774
DOI10.1016/S0045-2068(03)00040-3
ISSN0045-2068 (Print)
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