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

Research output: Contribution to journalArticlepeer-review

75 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1615-1621
Number of pages7
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume43
Issue number5
DOIs
StatePublished - Apr 11 2007
Externally publishedYes

Keywords

  • Dietary supplements
  • Liquid chromatography-mass spectrometry (LC-MS)
  • Methisosildenafil
  • Nuclear magnetic resonance (NMR)
  • Sildenafil analogue

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