Isolation and identification of a new sildenafil analogue adulterated in energy drink: propoxyphenyl sildenafil

J Pharm Biomed Anal. 2013 Jan:72:155-8. doi: 10.1016/j.jpba.2012.09.017. Epub 2012 Oct 12.

Abstract

A new sildenafil analogue was found to be added illegally to a energy drink marketed for the enhancement of sexual function. The structure was determined as 1-[4-propoxy-3-(6,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenylsulfonyl]-4-methylpiperazine. Owing to the inclusion of one more methyl group to sildenafil (on C-21), the detected compound was called "propoxyphenyl sildenafil". The sample was purified with column chromatography. The UV, IR, LC/MS (ESI) and completely assigned NMR data of propoxyphenyl sildenafil is reported. Having compared the structure with sildenafil, the results showed that the 2-ethoxy group (at the position on C-19) has been replaced by propoxy group.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, Liquid / methods
  • Energy Drinks / analysis*
  • Magnetic Resonance Spectroscopy / methods
  • Mass Spectrometry / methods
  • Piperazines / analysis*
  • Purines / analysis
  • Sildenafil Citrate
  • Spectrophotometry, Infrared / methods
  • Spectrophotometry, Ultraviolet / methods
  • Sulfones / analysis*

Substances

  • Piperazines
  • Purines
  • Sulfones
  • Sildenafil Citrate