Structure elucidation of a novel analogue of sildenafil detected as an adulterant in an herbal dietary supplement

descriptionPublicationkeyboard_double_arrow_right Article 01 Apr 2007 English Publisher:Elsevier BVJournal:Journal of Pharmaceutical and Biomedical Analysis, volume 43, pages 1,615-1,621 (issn: 0731-7085,

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Authors: Reepmeyer, John C.; Woodruff, Jeffrey T.; d'Avignon, D. André;

doi: 10.1016/j.jpba.2006.11.037

pmid: 17207601

Structure elucidation of a novel analogue of sildenafil detected as an adulterant in an herbal dietary supplement

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Abstract

A new analogue of sildenafil was detected in an herbal dietary supplement, which was sold over the internet and promoted as a product for the enhancement of sexual performance. The structure of the compound was established using LC-MS, UV spectroscopy, MS-MS, and NMR. In addition, the compound was cleaved at its sulfonamide S-N bond yielding a sulfonic acid and an amine, which were independently characterized using LC-MS, GC-MS, and derivatization. The compound, named methisosildenafil, is a novel synthetic analogue of sildenafil in which the N-methylpiperazine moiety has been replaced with 2,6-dimethylpiperazine.

Related Organizations

United States Food and Drug Administration
United States
Washington University in St. Louis
United States

Keywords

Male, Magnetic Resonance Spectroscopy, Molecular Structure, Phosphodiesterase Inhibitors, Plant Extracts, Food Contamination, Mass Spectrometry, Piperazines, Sildenafil Citrate, Designer Drugs, Erectile Dysfunction, Purines, Dietary Supplements, Humans, Spectrophotometry, Ultraviolet, Plant Preparations, Sulfones, Chromatography, Liquid

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