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

ALP M., Coskun M., GÖKER A. H.

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, vol.72, pp.155-158, 2013 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 72
  • Publication Date: 2013
  • Doi Number: 10.1016/j.jpba.2012.09.017
  • Journal Name: JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.155-158
  • Keywords: Sildenafil analogues, Propoxyphenyl sildenafil, Homosildenafil, Adulterants, PDE-5 inhibitors, ERECTILE DYSFUNCTION, HEALTH SUPPLEMENTS, DIETARY-SUPPLEMENT, THIOSILDENAFIL, INHIBITORS, ELUCIDATION, VARDENAFIL
  • Ankara University Affiliated: Yes

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Having compared the structure with sildenafil, the results showed that the 2-ethoxy group (at the position on C-19) has been replaced by propoxy group. (C) 2012 Elsevier B.V. All rights reserved.