title: Synthesis of 17β-hydroxymethyl-17α-methyl-18-norandrosta-1,4,13-trien-3-one: A long-term metandienone metabolite.
abstract: The goal of this work was a good-yielding chemical synthesis of a metandienone metabolite which is of interest in doping analysis. 20βOH-NorMD (IUPAC: 17β-hydroxymethyl-17α-methyl-18-norandrosta-1,4,13-triene-3-one) has been identified as a long-term urinary metabolite which can be detected and attributed to metandienone up to almost 3weeks after exposure. The chemical synthesis of its epimer 20αOH-NorMD has been described before, as was an enzymatic synthesis of 20βOH-NorMD, but no chemical synthesis was published.
authors.affiliation: Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, 1060 Vienna, Austria.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Kratena
authors.affiliation: Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, 1060 Vienna, Austria. Electronic address: valentin.enev@tuwien.ac.at.
authors.forename: Valentin S
authors.initials: VS
authors.lastname: Enev
authors.affiliation: Doping Control Laboratory, Seibersdorf Labor GmbH, 2444 Seibersdorf, Austria.
authors.forename: Günter
authors.initials: G
authors.lastname: Gmeiner
authors.affiliation: Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, 1060 Vienna, Austria. Electronic address: peter.gaertner@tuwien.ac.at.
authors.forename: Peter
authors.initials: P
authors.lastname: Gärtner
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003687:Dehydroepiandrosterone / Q000031:analogs & derivatives; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D008696:Methandrostenolone / Q000737:chemistry*; D015394:Molecular Structure; D014266:Trientine / Q000737:chemistry
chemical_list: D003687:Dehydroepiandrosterone; C028163:dehydroepiandrosterone acetate; D008696:Methandrostenolone; D014266:Trientine
keywords: Metabolism; Metandienone; Wagner-Meerwein rearrangement