Structure elucidation of a novel synthetic thiono analogue of sildenafil detected in an alleged herbal aphrodisiac

J Pharm Biomed Anal. 2008 Mar 13;46(4):814-7. doi: 10.1016/j.jpba.2007.12.007. Epub 2007 Dec 15.

Abstract

A new analogue of sildenafil was detected in a herbal aphrodisiac. The structure of the compound was established using LC-MS, UV and IR spectroscopy, MS-MS, and NMR. The compound, named thio-homosildenafil is a synthetic N-ethylpiperazine analogue of sildenafil in which also the CO moiety has been converted into a CS group. This is the first time a sildenafil analogue modified at the chromophore was identified as an adulterant of a herbal aphrodisiac. Preliminary pharmacological analysis confirmed the erectogenic potency of thio-homosildenafil.

MeSH terms

  • Chromatography, Liquid
  • Drug Contamination
  • Drugs, Chinese Herbal / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Phosphodiesterase Inhibitors / chemistry*
  • Piperazines / chemistry*
  • Piperazines / pharmacology
  • Purines / chemistry
  • Purines / pharmacology
  • Sildenafil Citrate
  • Sulfones / chemistry*
  • Sulfones / pharmacology

Substances

  • Drugs, Chinese Herbal
  • Phosphodiesterase Inhibitors
  • Piperazines
  • Purines
  • Sulfones
  • Sildenafil Citrate