title: Isolation and identification of hydroxythiohomosildenafil in herbal dietary supplements sold as sexual performance enhancement products.
abstract: 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.
authors.affiliation: Faculty of Science, Department of Pharmacy, National University of Singapore, Singapore.
authors.forename: L
authors.initials: L
authors.lastname: Li
authors.forename: M-Y
authors.initials: MY
authors.lastname: Low
authors.forename: F
authors.initials: F
authors.lastname: Aliwarga
authors.forename: J
authors.initials: J
authors.lastname: Teo
authors.forename: X-W
authors.initials: XW
authors.lastname: Ge
authors.forename: Y
authors.initials: Y
authors.lastname: Zeng
authors.forename: B C
authors.initials: BC
authors.lastname: Bloodworth
authors.forename: H-L
authors.initials: HL
authors.lastname: Koh
mesh_terms: D019587:Dietary Supplements / Q000009:adverse effects / Q000032:analysis*; D007172:Erectile Dysfunction / Q000628:therapy*; D005506:Food Contamination / Q000032:analysis*; D006801:Humans; D008297:Male; D013058:Mass Spectrometry / Q000379:methods; D010726:Phosphodiesterase Inhibitors / Q000009:adverse effects / Q000032:analysis* / Q000737:chemistry; D010879:Piperazines / Q000009:adverse effects / Q000032:analysis* / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry / Q000627:therapeutic use*; D011687:Purines / Q000009:adverse effects / Q000032:analysis / Q000737:chemistry; D000068677:Sildenafil Citrate; D013449:Sulfonamides; D013450:Sulfones / Q000009:adverse effects / Q000032:analysis* / Q000737:chemistry
chemical_list: D010726:Phosphodiesterase Inhibitors; D010879:Piperazines; D010936:Plant Extracts; D011687:Purines; D013449:Sulfonamides; D013450:Sulfones; C000595855:hydroxythiohomosildenafil; D000068677:Sildenafil Citrate