Structure elucidation of a novel analogue of sildenafil detected as an adulterant in an herbal dietary supplement

John C. Reepmeyer; Jeffrey T. Woodruff; D. André d'Avignon

doi:10.1016/j.jpba.2006.11.037

Structure elucidation of a novel analogue of sildenafil detected as an adulterant in an herbal dietary supplement

John C. Reepmeyer
, Jeffrey T. Woodruff
, D. André d'Avignon

Research output: Contribution to journal › Article › peer-review

80 Scopus citations

Abstract

A new analogue of sildenafil was detected in an herbal dietary supplement, which was sold over the internet and promoted as a product for the enhancement of sexual performance. The structure of the compound was established using LC-MS, UV spectroscopy, MS-MS, and NMR. In addition, the compound was cleaved at its sulfonamide S-N bond yielding a sulfonic acid and an amine, which were independently characterized using LC-MS, GC-MS, and derivatization. The compound, named methisosildenafil, is a novel synthetic analogue of sildenafil in which the N-methylpiperazine moiety has been replaced with 2,6-dimethylpiperazine.

Original language	English (US)
Pages (from-to)	1615-1621
Number of pages	7
Journal	Journal of Pharmaceutical and Biomedical Analysis
Volume	43
Issue number	5
DOIs	https://doi.org/10.1016/j.jpba.2006.11.037
State	Published - Apr 11 2007
Externally published	Yes

Keywords

Dietary supplements
Liquid chromatography-mass spectrometry (LC-MS)
Methisosildenafil
Nuclear magnetic resonance (NMR)
Sildenafil analogue

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10.1016/j.jpba.2006.11.037

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title = "Structure elucidation of a novel analogue of sildenafil detected as an adulterant in an herbal dietary supplement",

abstract = "A new analogue of sildenafil was detected in an herbal dietary supplement, which was sold over the internet and promoted as a product for the enhancement of sexual performance. The structure of the compound was established using LC-MS, UV spectroscopy, MS-MS, and NMR. In addition, the compound was cleaved at its sulfonamide S-N bond yielding a sulfonic acid and an amine, which were independently characterized using LC-MS, GC-MS, and derivatization. The compound, named methisosildenafil, is a novel synthetic analogue of sildenafil in which the N-methylpiperazine moiety has been replaced with 2,6-dimethylpiperazine.",

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doi = "10.1016/j.jpba.2006.11.037",

language = "English (US)",

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AU - Reepmeyer, John C.

AU - Woodruff, Jeffrey T.

AU - d'Avignon, D. André

PY - 2007/4/11

Y1 - 2007/4/11

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KW - Dietary supplements

KW - Liquid chromatography-mass spectrometry (LC-MS)

KW - Methisosildenafil

KW - Nuclear magnetic resonance (NMR)

KW - Sildenafil analogue

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Structure elucidation of a novel analogue of sildenafil detected as an adulterant in an herbal dietary supplement

Abstract

Keywords

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