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

被引：74
|
作者：
Reepmeyer, John C. [1 ]
Woodruff, Jeffrey T.
d'Avignon, D. Andre
机构：
[1] US FDA, Div Pharmaceut Anal, St Louis, MO 63101 USA
[2] Washington Univ, Dept Chem, St Louis, MO 63130 USA
来源：
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS | 2007年 / 43卷 / 05期
关键词：
dietary supplements; sildenafil analogue; methisosildenafil; liquid chromatography-mass spectrometry (LC-MS); nuclear magnetic resonance (NMR);
D O I：
10.1016/j.jpba.2006.11.037
中图分类号：
O65 [分析化学];
学科分类号：
070302 ; 081704 ;
摘要：
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. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码：1615 / 1621
页数：7
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