publication . Article . 2007

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

John C. Reepmeyer; Jeffrey T. Woodruff; D. André d’Avignon;
Open Access
  • Published: 01 Apr 2007
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.
Persistent Identifiers
free text keywords: Clinical Biochemistry, Spectroscopy, Drug Discovery, Pharmaceutical Science, Analytical Chemistry, Enzyme inhibitor, biology.protein, biology, Sulfonic acid, chemistry.chemical_classification, chemistry, Amine gas treating, Adulterant, Derivatization, chemistry.chemical_compound, Moiety, Organic chemistry, Liquid chromatography–mass spectrometry, Chromatography, Sildenafil
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