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J Pharm Biomed Anal. 2007 Apr 11;43(5):1615-21. Epub 2007 Jan 4.

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

Author information

  • 1US Food and Drug Administration, Division of Pharmaceutical Analysis, St. Louis, MO 63101, USA. john.reepmeyer@fda.hhs.gov

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.

PMID:
17207601
[PubMed - indexed for MEDLINE]
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