Identification of a new sildenafil analogue in a health supplement

J Pharm Biomed Anal. 2011 Nov 1;56(3):491-6. doi: 10.1016/j.jpba.2011.06.004. Epub 2011 Jun 15.

Abstract

A sildenafil analogue was detected and isolated from a health supplement claimed for human use. The structure of this new analogue was elucidated using LC-UV, LC-Orbitrap-MS, IR spectroscopy, 1D and 2D NMR. It was characterized as dithio-desmethylcarbodenafil containing 2 thiocarbonyl groups instead of 2 carbonyl groups, and 4-methyl substitution, on the piperazine ring, rather than 4-ethyl substitution, when compared to sildenafil.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, Liquid / methods
  • Dietary Supplements / analysis*
  • Drug Contamination*
  • Humans
  • Magnetic Resonance Spectroscopy / methods
  • Mass Spectrometry / methods
  • Piperazine
  • Piperazines / chemistry*
  • Piperazines / isolation & purification
  • Purines / chemistry
  • Purines / isolation & purification
  • Sildenafil Citrate
  • Spectrophotometry, Infrared / methods
  • Spectrophotometry, Ultraviolet / methods
  • Sulfones / chemistry*
  • Sulfones / isolation & purification

Substances

  • Piperazines
  • Purines
  • Sulfones
  • Piperazine
  • Sildenafil Citrate