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Synthesis of a human long-term oxymetholone metabolite.

Abstract

A long-term metabolite of the doping agent oxymetholone (OXM-M2, 17β-hydroxymethyl-2,17α-methyl-18-norandrost-13-en-3-one) which has been identified by GC-MS/MS was synthesized from commercially available materials. Two efficient synthetic routes to access both C-17 epimers of tentative metabolites were developed. The identity and molecular configuration of the in vivo metabolite: 17β-hydroxymethyl-2α,17α-methyl-18-norandrost-13-en-3-one was confirmed by single crystal X-ray diffraction.

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  • Authors+Show Affiliations

    ,

    Institute of Applied Synthetic Chemistry, Vienna University of Technology, Austria.

    ,

    Institute of Applied Synthetic Chemistry, Vienna University of Technology, Austria.

    ,

    Doping Control Laboratory, Seibersdorf Labor GmbH, Austria.

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    Doping Control Laboratory, Seibersdorf Labor GmbH, Austria.

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    Institute for Chemical Technologies and Analytics, Vienna University of Technology, Austria.

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    Institute of Applied Synthetic Chemistry, Vienna University of Technology, Austria. Electronic address: valentin.enev@tuwien.ac.at.

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    Doping Control Laboratory, Seibersdorf Labor GmbH, Austria.

    Institute of Applied Synthetic Chemistry, Vienna University of Technology, Austria. Electronic address: peter.gaertner@tuwien.ac.at.

    Source

    Steroids 150: 2019 Jun 20 pg 108430

    Pub Type(s)

    Journal Article

    Language

    eng

    PubMed ID

    31229510

    Citation

    Kratena, Nicolas, et al. "Synthesis of a Human Long-term Oxymetholone Metabolite." Steroids, vol. 150, 2019, p. 108430.
    Kratena N, Biedermann N, Stojanovic B, et al. Synthesis of a human long-term oxymetholone metabolite. Steroids. 2019;150:108430.
    Kratena, N., Biedermann, N., Stojanovic, B., Göschl, L., Weil, M., Enev, V. S., ... Gärtner, P. (2019). Synthesis of a human long-term oxymetholone metabolite. Steroids, 150, p. 108430. doi:10.1016/j.steroids.2019.108430.
    Kratena N, et al. Synthesis of a Human Long-term Oxymetholone Metabolite. Steroids. 2019 Jun 20;150:108430. PubMed PMID: 31229510.
    * Article titles in AMA citation format should be in sentence-case
    TY - JOUR T1 - Synthesis of a human long-term oxymetholone metabolite. AU - Kratena,Nicolas, AU - Biedermann,Nina, AU - Stojanovic,Biljana, AU - Göschl,Lorenz, AU - Weil,Matthias, AU - Enev,Valentin S, AU - Gmeiner,Günter, AU - Gärtner,Peter, Y1 - 2019/06/20/ PY - 2019/04/09/received PY - 2019/05/29/revised PY - 2019/06/17/accepted PY - 2019/6/24/pubmed PY - 2019/6/24/medline PY - 2019/6/24/entrez KW - Long-term metabolite KW - Oxymetholone KW - Total synthesis SP - 108430 EP - 108430 JF - Steroids JO - Steroids VL - 150 N2 - A long-term metabolite of the doping agent oxymetholone (OXM-M2, 17β-hydroxymethyl-2,17α-methyl-18-norandrost-13-en-3-one) which has been identified by GC-MS/MS was synthesized from commercially available materials. Two efficient synthetic routes to access both C-17 epimers of tentative metabolites were developed. The identity and molecular configuration of the in vivo metabolite: 17β-hydroxymethyl-2α,17α-methyl-18-norandrost-13-en-3-one was confirmed by single crystal X-ray diffraction. SN - 1878-5867 UR - https://www.unboundmedicine.com/medline/citation/31229510/Synthesis_of_a_human_long-term_oxymetholone_metabolite L2 - https://linkinghub.elsevier.com/retrieve/pii/S0039-128X(19)30120-5 DB - PRIME DP - Unbound Medicine ER -