Structure elucidation of a novel synthetic thiono analogue of sildenafil detected in an alleged herbal aphrodisiac.
A new analogue of sildenafil was detected in a herbal aphrodisiac. The structure of the compound was established using LC-MS, UV and IR spectroscopy, MS-MS, and NMR. The compound, named thio-homosildenafil is a synthetic N-ethylpiperazine analogue of sildenafil in which also the CO moiety has been converted into a CS group. This is the first time a sildenafil analogue modified at the chromophore was identified as an adulterant of a herbal aphrodisiac. Preliminary pharmacological analysis confirmed the erectogenic potency of thio-homosildenafil.
Venhuis
B J
BJ
National Institute for Public Health and the Environment, Postbox 1, 3720 BA, Bilthoven, The Netherlands.
Zomer
G
G
de Kaste
D
D
D002853:Chromatography, Liquid; D004340:Drug Contamination; D004365:Drugs, Chinese Herbal / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010726:Phosphodiesterase Inhibitors / Q000737:chemistry*; D010879:Piperazines / Q000737:chemistry* / Q000494:pharmacology; D011687:Purines / Q000737:chemistry / Q000494:pharmacology; D000068677:Sildenafil Citrate; D013450:Sulfones / Q000737:chemistry* / Q000494:pharmacology
D004365:Drugs, Chinese Herbal; D010726:Phosphodiesterase Inhibitors; D010879:Piperazines; D011687:Purines; D013450:Sulfones; D000068677:Sildenafil Citrate