Isolation and identification of a new sildenafil analogue, hydroxycarbodenafil, found as an adulterant in a health supplement

J Pharm Biomed Anal. 2020 Jun 5:185:113222. doi: 10.1016/j.jpba.2020.113222. Epub 2020 Feb 29.

Abstract

During routine screening of illegal adulterants in health supplements, a novel sildenafil analogue was discovered, and subsequently isolated by recrystallization. Its structure was elucidated by extensive analyses of high resolution mass spectrometry (HRMS), one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) data. The analogue was finally determined as hydroxycarbodenafil, featuring a hydroxyethyl group instead of an ethyl group on piperazine ring in comparison with carbodenafil.

Keywords: Adulterated health supplement; HR-MS and NMR; Hydroxycarbodenafil; Sildenafil analogue.

MeSH terms

  • Dietary Supplements / analysis*
  • Dietary Supplements / standards
  • Drug Contamination / prevention & control*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Sildenafil Citrate / analogs & derivatives
  • Sildenafil Citrate / analysis*
  • Sildenafil Citrate / standards

Substances

  • Sildenafil Citrate