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Synthesis of a human long-term oxymetholone metabolite.
Steroids 2019; 150:108430S

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.

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.Doping Control Laboratory, Seibersdorf Labor GmbH, Austria.Institute for Chemical Technologies and Analytics, Vienna University of Technology, Austria.Institute of Applied Synthetic Chemistry, Vienna University of Technology, Austria. Electronic address: valentin.enev@tuwien.ac.at.Doping Control Laboratory, Seibersdorf Labor GmbH, Austria.Institute of Applied Synthetic Chemistry, Vienna University of Technology, Austria. Electronic address: peter.gaertner@tuwien.ac.at.

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;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 -