sildenafil-citrate and methisosildenafil

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.

Topics: Chromatography, Liquid; Designer Drugs; Dietary Supplements; Erectile Dysfunction; Food Contamination; Humans; Magnetic Resonance Spectroscopy; Male; Mass Spectrometry; Molecular Structure; Phosphodiesterase Inhibitors; Piperazines; Plant Extracts; Plant Preparations; Purines; Sildenafil Citrate; Spectrophotometry, Ultraviolet; Sulfones