Analysis of herbal dietary supplements for sexual performance enhancement: first characterization of propoxyphenyl-thiohydroxyhomosildenafil and identification of sildenafil, thiosildenafil, phentolamine and tetrahydropalmatine as adulterants

J Pharm Biomed Anal. 2012 Apr 7:63:135-50. doi: 10.1016/j.jpba.2012.01.035. Epub 2012 Feb 4.

Abstract

Nine herbal dietary supplements intended to be beverages for enhancing sexual performance were analyzed before their possible launch on the market. Four of them contained a sildenafil analog reported for the first time as an adulterant. After isolation and characterization using NMR, MS, IR and UV, this analog was named propoxyphenyl-thiohydroxyhomosildenafil as the ethoxy chain on the phenyl ring of the already known analog thiohydroxyhomosildenafil was replaced by a propoxy moiety. One formulation was tainted with thiosildenafil, another unapproved PDE-5 inhibitor. Sildenafil along with the natural alkaloid tetrahydropalmatine that has no documented effect for enhancing erectile dysfunction were identified in two formulations. Another formulation was adulterated with phentolamine, a drug that is not approved for boosting male sexual performance when taken orally. The last formulation containing osthole, a bioactive natural coumarine improving sexual dysfunction, is most probably truly natural.

MeSH terms

  • Aphrodisiacs / analysis*
  • Aphrodisiacs / pharmacology
  • Berberine Alkaloids / analysis*
  • Berberine Alkaloids / pharmacology
  • Dietary Supplements / analysis*
  • Drug Contamination*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Male
  • Molecular Structure
  • Penile Erection / drug effects
  • Phentolamine / analysis*
  • Phentolamine / pharmacology
  • Phosphodiesterase 5 Inhibitors / analysis*
  • Phosphodiesterase 5 Inhibitors / pharmacology
  • Piperazines / analysis*
  • Piperazines / pharmacology
  • Plant Preparations / analysis*
  • Plant Preparations / pharmacology
  • Purines / analysis
  • Purines / pharmacology
  • Sexual Behavior / drug effects
  • Sildenafil Citrate
  • Spectrophotometry, Ultraviolet
  • Spectroscopy, Fourier Transform Infrared
  • Sulfhydryl Compounds / analysis*
  • Sulfhydryl Compounds / pharmacology
  • Sulfones / analysis*
  • Sulfones / pharmacology
  • Tandem Mass Spectrometry

Substances

  • Aphrodisiacs
  • Berberine Alkaloids
  • Phosphodiesterase 5 Inhibitors
  • Piperazines
  • Plant Preparations
  • Purines
  • Sulfhydryl Compounds
  • Sulfones
  • tetrahydropalmatine
  • Sildenafil Citrate
  • Phentolamine