title: Identification of novel sildenafil-analogues in an adulterated herbal food supplement.
abstract: A new herbal product advertised as potency pill was sent for analysis by the local authority. The product was tested for the presence of potential derivatives of PDE-5 inhibitors, such as sildenafil, vardenafil, and tadalafil. Sildenafil analogues were identified, in which the piperazine ring and the sulfonyl group were replaced by a piperazinone and a hydroxyethyl structure, respectively. The chemical structures were established by LC-MS in ESI negative mode, UV and NMR spectroscopy (including DEPT, HSQC, HMBC, H,H-COSY, H,H-TOCSY and H,H-NOESY experiments). This is the first report of piperazinonafil and isopiperazinonafil as adulterant in an herbal food supplement.
authors.affiliation: Bavarian Health and Food Safety Authority, Veterinärstr. 2, 85764 Oberschleißheim, Germany.
authors.forename: Uwe
authors.initials: U
authors.lastname: Wollein
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Eisenreich
authors.forename: Nicholas
authors.initials: N
authors.lastname: Schramek
mesh_terms: D002243:Carbolines / Q000032:analysis* / Q000737:chemistry; D019587:Dietary Supplements / Q000032:analysis*; D004340:Drug Contamination; D005506:Food Contamination; D006801:Humans; D007093:Imidazoles / Q000032:analysis* / Q000737:chemistry; D008297:Male; D058986:Phosphodiesterase 5 Inhibitors / Q000032:analysis* / Q000737:chemistry; D010879:Piperazines / Q000032:analysis* / Q000737:chemistry; D028321:Plant Preparations / Q000032:analysis* / Q000737:chemistry; D011687:Purines / Q000032:analysis / Q000737:chemistry; D000068677:Sildenafil Citrate; D013450:Sulfones / Q000032:analysis* / Q000737:chemistry; D000068581:Tadalafil; D014227:Triazines / Q000032:analysis / Q000737:chemistry; D000069058:Vardenafil Dihydrochloride
chemical_list: D002243:Carbolines; D007093:Imidazoles; D058986:Phosphodiesterase 5 Inhibitors; D010879:Piperazines; D028321:Plant Preparations; D011687:Purines; D013450:Sulfones; D014227:Triazines; D000069058:Vardenafil Dihydrochloride; D000068581:Tadalafil; D000068677:Sildenafil Citrate