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

J Pharm Biomed Anal. 2007 Apr 11;43(5):1615-21. doi: 10.1016/j.jpba.2006.11.037. Epub 2007 Jan 4.

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.

MeSH terms

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

Substances

  • Designer Drugs
  • Phosphodiesterase Inhibitors
  • Piperazines
  • Plant Extracts
  • Plant Preparations
  • Purines
  • Sulfones
  • methisosildenafil
  • Sildenafil Citrate