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Synthesis of human long-term metabolites of dehydrochloromethyltestosterone and oxymesterone.

Authors
  • Kratena, Nicolas1
  • Pfeffer, Sandra2
  • Enev, Valentin S3
  • Gmeiner, Günter2
  • Gärtner, Peter4
  • 1 Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria. , (Austria)
  • 2 Doping Control Laboratory, Seibersdorf Labor GmbH, 2444 Seibersdorf, Austria. , (Austria)
  • 3 Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria. Electronic address: [email protected] , (Austria)
  • 4 Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060 Vienna, Austria. Electronic address: [email protected] , (Austria)
Type
Published Article
Journal
Steroids
Publication Date
Aug 26, 2020
Volume
164
Pages
108716–108716
Identifiers
DOI: 10.1016/j.steroids.2020.108716
PMID: 32860782
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

We herein report the synthesis of the long-term metabolites "M4" (IUPAC: 4-chloro-17-hydroxymethyl-17-methyl-18-norandrosta-4,13-dien-3-ol) of dehydrochloromethyl-testosterone (DHCMT, Oral Turinabol) and "Oxy M9" (4-hydroxy-17β-hydroxymethyl-17α-methyl-18-norandrosta-4,13-dien-3-one) of oxymesterone (Oranabol). Both compounds were derived from a common synthetic route starting from dehydroepiandrosterone acetate. Four different stereoisomers were evaluated for metabolite M4. The previously assigned structure could be corrected regarding the C-3 and C-17 stereocenters. Copyright © 2020 The Authors. Published by Elsevier Inc. All rights reserved.

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