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.
MeSH terms
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Chromatography, Liquid
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Designer Drugs / analysis
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Designer Drugs / chemistry
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Dietary Supplements / analysis*
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Erectile Dysfunction / diet therapy
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Food Contamination*
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Humans
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Magnetic Resonance Spectroscopy
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Male
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Mass Spectrometry
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Molecular Structure
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Phosphodiesterase Inhibitors / chemistry
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Piperazines / analysis
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Piperazines / chemistry*
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Plant Extracts / analysis*
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Plant Preparations / analysis
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Plant Preparations / chemistry
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Purines / analysis
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Purines / chemistry
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Sildenafil Citrate
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Spectrophotometry, Ultraviolet
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Sulfones / analysis
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Sulfones / chemistry*
Substances
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Designer Drugs
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Phosphodiesterase Inhibitors
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Piperazines
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Plant Extracts
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Plant Preparations
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Purines
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Sulfones
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methisosildenafil
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Sildenafil Citrate