title: A facile and high yielding synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide--an internal standard in dope.
abstract: A facile six-step synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide (1) starting from epiandrosterone (2) in 63% yield is described and compared with several alternative synthetic pathways. Compound 1 can be used as an internal standard in screening procedures for anabolic steroids to monitor the hydrolysis step of the steroid glucuronides prior to gas chromatography-mass spectrometry (GC-MS) analysis. Thus, a time consuming solid-phase extraction step to remove possible hydrolysis inhibitors can be omitted.
authors.affiliation: Institute of Organic Chemistry, Vienna University of Technology, Getreidemarkt 9, A-1060 Vienna, Austria. pgaertner@mail.zserv.tuwien.ac.at
authors.forename: Peter
authors.initials: P
authors.lastname: Gärtner
authors.forename: Clemens
authors.initials: C
authors.lastname: Novak
authors.forename: Christian
authors.initials: C
authors.lastname: Einzinger
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Felzmann
authors.forename: Max
authors.initials: M
authors.lastname: Knollmüller
authors.forename: Günter
authors.initials: G
authors.lastname: Gmeiner
authors.forename: Wilhelm
authors.initials: W
authors.lastname: Schänzer
mesh_terms: D045930:Anabolic Agents / Q000592:standards / Q000652:urine*; D000738:Androsterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000592:standards; D003903:Deuterium; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D006868:Hydrolysis; D013287:Illicit Drugs / Q000652:urine*; D008403:Mass Screening / Q000379:methods; D012015:Reference Standards
chemical_list: D045930:Anabolic Agents; D013287:Illicit Drugs; C027927:androsterone glucuronide; D003903:Deuterium; D000738:Androsterone