Structure elucidation of sildenafil analogues in herbal products.

Abstract

The structure of unknown compounds present in herbal products was elucidated using liquid chromatography-electrospray ionization-mass spectrometry, direct-infusion electrospray ionization-mass spectrometry, and nuclear magnetic resonance. Compounds 1-3 were identified as sildenafil analogues, 1 bearing an N-ethylpiperazine moiety instead of an N-methylpiperazine, and an acetyl group instead of the sulfonyl group, named acetildenafil, 2 bearing an N-ethylpiperazine moiety instead of an N-methylpiperazine (homosildenafil), and 3 bearing an N-hydroxylethylpiperazine moiety instead of an N-methylpiperazine, named hydroxyhomosildenafil. When analysing products marketed for penile erectile dysfunction or marketed as aphrodisiacs, attention should be given to the possible presence of these components.

• Authors: L Blok-Tip, B Zomer, F Bakker, K D Hartog, M Hamzink, J Ten Hove, M Vredenbregt, D De Kaste
• Journal: Food additives and contaminants (Food Addit Contam) Vol. 21 Issue 8 Pg. 737-48 (Aug 2004) ISSN: 0265-203X [Print] England
• PMID: 15370823 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Carbolines
• Imidazoles
• Phosphodiesterase Inhibitors
• Piperazines
• Plant Preparations
• Purines
• Sulfones
• Triazines
• Vasodilator Agents
• Vardenafil Dihydrochloride
• Tadalafil
• Sildenafil Citrate

Topics

• Carbolines (chemistry)
• Chromatography, Liquid (methods)
• Imidazoles (chemistry)
• Magnetic Resonance Spectroscopy (methods)
• Models, Chemical
• Phosphodiesterase Inhibitors (chemistry)
• Piperazines (chemistry)
• Plant Preparations (chemistry)
• Purines
• Sildenafil Citrate
• Spectrometry, Mass, Electrospray Ionization (methods)
• Sulfones
• Tadalafil
• Triazines
• Vardenafil Dihydrochloride
• Vasodilator Agents (chemistry)