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, cilt.72, ss.155-158, 2013 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 72
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1016/j.jpba.2012.09.017
  • Dergi Adı: JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.155-158
  • Anahtar Kelimeler: Sildenafil analogues, Propoxyphenyl sildenafil, Homosildenafil, Adulterants, PDE-5 inhibitors, ERECTILE DYSFUNCTION, HEALTH SUPPLEMENTS, DIETARY-SUPPLEMENT, THIOSILDENAFIL, INHIBITORS, ELUCIDATION, VARDENAFIL
  • Ankara Üniversitesi Adresli: Evet

Özet

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Having compared the structure with sildenafil, the results showed that the 2-ethoxy group (at the position on C-19) has been replaced by propoxy group.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.