TY - JOUR
T1 - Structure elucidation of a novel analogue of sildenafil detected as an adulterant in an herbal dietary supplement
AU - Reepmeyer, John C.
AU - Woodruff, Jeffrey T.
AU - d'Avignon, D. André
PY - 2007/4/11
Y1 - 2007/4/11
N2 - 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.
AB - 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.
KW - Dietary supplements
KW - Liquid chromatography-mass spectrometry (LC-MS)
KW - Methisosildenafil
KW - Nuclear magnetic resonance (NMR)
KW - Sildenafil analogue
UR - http://www.scopus.com/inward/record.url?scp=33947498162&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33947498162&partnerID=8YFLogxK
U2 - 10.1016/j.jpba.2006.11.037
DO - 10.1016/j.jpba.2006.11.037
M3 - Article
C2 - 17207601
AN - SCOPUS:33947498162
SN - 0731-7085
VL - 43
SP - 1615
EP - 1621
JO - Journal of Pharmaceutical and Biomedical Analysis
JF - Journal of Pharmaceutical and Biomedical Analysis
IS - 5
ER -