Identification of a novel sildenafil analogue in an adulterated herbal supplement.
iErect, a new dietary supplement marketed as "100% natural" and sold over the Internet, was analyzed. It contains thiosildenafil, a sildenafil analogue already reported as an adulterant in herbal formulations, and a new compound whose structure was elucidated after isolation using NMR, MS and IR. It was named depiperazinothiosildenafil as it results from the hydrolytic cleavage of the S-N bond of the sulfonamide group of thiosildenafil. A capsule of iErect contains a very high amount (≈220mg) of thiosildenafil and ≈30mg of depiperazinothiosildenafil, which places consumers at risk for potentially serious side-effects.
Groupe de RMN Biomédicale, Laboratoire SPCMIB (UMR CNRS 5068), Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex, France.
Julie
J
Vaysse
Véronique
V
Gilard
Stéphane
S
Balayssac
Chantal
C
Zedde
Robert
R
Martino
Myriam
M
Malet-Martino
D002214:Capsules; D002851:Chromatography, High Pressure Liquid; D019587:Dietary Supplements / Q000032:analysis* / Q000592:standards*; D004340:Drug Contamination / Q000331:legislation & jurisprudence; D009682:Magnetic Resonance Spectroscopy; D010879:Piperazines / Q000737:chemistry / Q000302:isolation & purification*; D028321:Plant Preparations / Q000032:analysis* / Q000592:standards*; D011687:Purines / Q000737:chemistry / Q000302:isolation & purification; D011743:Pyrimidines / Q000737:chemistry / Q000302:isolation & purification*; D000068677:Sildenafil Citrate; D017550:Spectroscopy, Fourier Transform Infrared; D013450:Sulfones / Q000737:chemistry / Q000302:isolation & purification*; D053719:Tandem Mass Spectrometry; D013871:Thiones / Q000737:chemistry / Q000302:isolation & purification*
D002214:Capsules; D010879:Piperazines; D028321:Plant Preparations; D011687:Purines; D011743:Pyrimidines; D013450:Sulfones; D013871:Thiones; C572399:depiperazinothiosildenafil; D000068677:Sildenafil Citrate; C539492:thiosildenafil