Isolation and identification of hydroxythiohomosildenafil in herbal dietary supplements sold as sexual performance enhancement products. 2009

L Li, and M-Y Low, and F Aliwarga, and J Teo, and X-W Ge, and Y Zeng, and B C Bloodworth, and H-L Koh
Faculty of Science, Department of Pharmacy, National University of Singapore, Singapore.

An unknown compound is detected and isolated from two herbal dietary supplements bought on the internet. The structure of the unknown compound is elucidated using ESI-MS/MS, NMR, UV and IR. The compound, named hydroxythiohomosildenafil, is identified as an analogue of sildenafil in which the oxygen atom is substituted with a sulfur atom in the pyrazolopyrimidine moiety, and a hydroxyethyl group instead of a methyl group is attached to the piperazinyl nitrogen. It is the first report of this compound being detected in herbal dietary supplements. The UV, IR and completely assigned NMR data of hydroxythiohomosildenafil is recorded.

UI MeSH Term Description Entries
D007172 Erectile Dysfunction The inability in the male to have a PENILE ERECTION due to psychological or organ dysfunction. Impotence,Male Impotence,Male Sexual Impotence,Dysfunction, Erectile,Impotence, Male,Impotence, Male Sexual,Sexual Impotence, Male
D008297 Male Males
D010726 Phosphodiesterase Inhibitors Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases. Phosphodiesterase Antagonists,Phosphodiesterase Inhibitor,Phosphoric Diester Hydrolase Inhibitors,Antiphosphodiesterases,Inhibitor, Phosphodiesterase
D010879 Piperazines Compounds that are derived from PIPERAZINE.
D010936 Plant Extracts Concentrated pharmaceutical preparations of plants obtained by removing active constituents with a suitable solvent, which is evaporated away, and adjusting the residue to a prescribed standard. Herbal Medicines,Plant Extract,Extract, Plant,Extracts, Plant,Medicines, Herbal
D011687 Purines A series of heterocyclic compounds that are variously substituted in nature and are known also as purine bases. They include ADENINE and GUANINE, constituents of nucleic acids, as well as many alkaloids such as CAFFEINE and THEOPHYLLINE. Uric acid is the metabolic end product of purine metabolism.
D005506 Food Contamination The presence in food of harmful, unpalatable, or otherwise objectionable foreign substances, e.g. chemicals, microorganisms or diluents, before, during, or after processing or storage. Food Adulteration,Adulteration, Food,Adulterations, Food,Contamination, Food,Contaminations, Food,Food Adulterations,Food Contaminations
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000068677 Sildenafil Citrate A PHOSPHODIESTERASE TYPE-5 INHIBITOR; VASODILATOR AGENT and UROLOGICAL AGENT that is used in the treatment of ERECTILE DYSFUNCTION and PRIMARY PULMONARY HYPERTENSION. 1-((3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine citrate,Acetildenafil,Desmethyl Sildenafil,Desmethylsildenafil,Homosildenafil,Hydroxyhomosildenafil,NCX-911,Revatio,Sildenafil,Sildenafil Lactate,Sildenafil Nitrate,UK 92480-10,UK-92,480-10,Viagra,Citrate, Sildenafil,Lactate, Sildenafil,NCX 911,NCX911,Nitrate, Sildenafil,Sildenafil, Desmethyl,UK 92,480 10,UK 92480 10,UK 9248010
D013058 Mass Spectrometry An analytical method used in determining the identity of a chemical based on its mass using mass analyzers/mass spectrometers. Mass Spectroscopy,Spectrometry, Mass,Spectroscopy, Mass,Spectrum Analysis, Mass,Analysis, Mass Spectrum,Mass Spectrum Analysis,Analyses, Mass Spectrum,Mass Spectrum Analyses,Spectrum Analyses, Mass

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