We isolated a new illegal sildenafil analogue named mutaprodenafil from a dietary supplement for erectile dysfunction (ED) and proposed that it is an aildenafil derivative containing an imidazole moiety. We subsequently synthesized mutaprodenafil from a thioaildenafil and authenticated its structure.
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A revisited structure for nitrosoprodenafil from NMR, mass spectrometry, X-ray and hydrolysis data.
J Pharm Biomed Anal
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Laboratoire SPCMIB (UMR CNRS 5068), Université Paul Sabatier, Université de Toulouse, 118 route de Narbonne, 31062 Toulouse cedex, France. Electronic address:
The sildenafil analogue adulterant previously identified as a nitroso derivative (nitrosoprodenafil) in a dietary supplement (DS) marketed to increase sexual performance and sold in Europe in the early 2010s is the same as that found in the same type of DS available in Japan whose structure was established as a nitro derivative (mutaprodenafil or nitroprodenafil). Indeed, the compound isolated from the Man Power DS has identical UV, IR, NMR and MS spectroscopic characteristics and hydrolysis behavior than nitrosoprode-nafil. By revisiting its NMR assignments and MS and MS/MS data interpretation, it is demonstrated that the compound is actually a nitrothioimidazole-methisosildenafil hybrid, i.
View Article and Find Full Text PDF[Analysis and identification of illegal constituents in health food products implicitly advertizing tonic or slimming effect in the National Institute of Health Sciences in Japan].
Yakugaku Zasshi
September 2014
Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences.
With the prefectural governments' aid of the purchase, the Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences (NIHS) successively has surveyed illegal constituents in health food products implicitly advertizing tonic or slimming effect since the fiscal year of 2002 (slimming type) or 2003 (tonic type). The average numbers of the analyzed products per year are about 100 (slimming type) and 150 (tonic type), respectively. We also continuously distribute standards of authentic samples of several illegal components such as N-nitrosofenfluramine (NFF) and sildenafil (SIL) to prefectural institutes and the average gross number per year is about 140.
View Article and Find Full Text PDFStructure elucidation of a novel analog of sildenafil detected as an adulterant in a dietary supplement using LC-UV and LC/MS.
J AOAC Int
October 2012
Tokyo Metropolitan Institute of Public Health, Department of Pharmaceutical Sciences, 24-1 Hyakunincho 3-chome, Shinjuku-ku, Tokyo 169-0073, Japan.
A sildenafil-related compound was detected in a dietary supplement marketed as an aphrodisiac. The compound was detected during analysis of the dietary supplement using LC-UV and LC/electrospray ionization-MS. The structure of the compound was established using high resolution MS, NMR spectrometry, and X-ray crystal structure analysis.
View Article and Find Full Text PDFIdentification of mutaprodenafil in a dietary supplement and its subsequent synthesis.
Chem Pharm Bull (Tokyo)
June 2012
National Institute of Health Sciences, Tokyo, Japan.
We isolated a new illegal sildenafil analogue named mutaprodenafil from a dietary supplement for erectile dysfunction (ED) and proposed that it is an aildenafil derivative containing an imidazole moiety. We subsequently synthesized mutaprodenafil from a thioaildenafil and authenticated its structure.
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