912291-78-2

Basic information

• Product Name: 17β-HydroxyMethyl-17α-Methyl-18-norandrosta-1,4,13-trien-3-one
• Synonyms: 17β-HydroxyMethyl-17α-Methyl-18-norandrosta-1,4,13-trien-3-one
• CAS NO: 912291-78-2
• Molecular Formula: C₂₀H₂₆O₂
• Molecular Weight: 298.41924
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Metabolites & Impurities
• Mol File: 912291-78-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 17β-HydroxyMethyl-17α-Methyl-18-norandrosta-1,4,13-trien-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 17β-HydroxyMethyl-17α-Methyl-18-norandrosta-1,4,13-trien-3-one(912291-78-2)
• EPA Substance Registry System: 17β-HydroxyMethyl-17α-Methyl-18-norandrosta-1,4,13-trien-3-one(912291-78-2)

Safety Data

• Hazardous Substances Data: 912291-78-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 912291-78-2 differently. You can refer to the following data:
1. A new urinary metabolite of the human doping Metandienone (Methandrostenolone, M226000). This metabolite was reported to be detected in urine samples up to 19 days after administration of Metandienone.
2. 17β-Hydroxymethyl-17α-methyl-18-norandrosta-1,4,13-trien-3-one is a new urinary labelled metabolite of the human doping Metandienone (Methandrostenolone, M226000). This metabolite was reported to be detected in urine samples up to 19 days after administration of Metandienone.

Upstream product

• 55706-91-7 spiro(13α-methylandrost-1,4-dien-17,2'-oxirane)-3-one 
• 77702-25-1 17,17-dimethyl-18-norandrosta-1,4,13⁽¹⁴⁾-trien-3-one 
• 94991-86-3 3β,14α-dihydroxy-androst-5-en-17-one 
• 1443-89-6 3β-acetoxy-14α-hydroxyandrost-5-en-17-one 

Relevant articles and documents

Synthesis of 17β-hydroxymethyl-17α-methyl-18-norandrosta-1,4,13-trien-3-one: A long-term metandienone metabolite

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 3?weeks 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.

CYP21-catalyzed production of the long-term urinary metandienone metabolite 17β-hydroxymethyl-17α-methyl-18-norandrosta-1,4,13-trien-3-one: A contribution to the fight against doping

Anabolic-androgenic steroids are some of the most frequently misused drugs in human sports. Recently, a previously unknown urinary metabolite of metandienone, 17β-hydroxymethyl-17α-methyl-18-norandrosta-1,4,13- trien-3-one (20OH-NorMD), was discovered via LC-MS/MS and GC-MS. This metabolite was reported to be detected in urine samples up to 19 days after administration of metandienone. However, so far it was not possible to obtain purified reference material of this metabolite and to confirm its structure via NMR. Eleven recombinant strains of the fission yeast Schizosaccharomyces pombe that express different human hepatic or steroidogenic cytochrome P450 enzymes were screened for production of this metabolite in a whole-cell biotransformation reaction. 17,17-Dimethyl-18-norandrosta-1,4,13-trien-3-one, chemically derived from metandienone, was used as substrate for the bioconversion, because it could be converted to the final product in a single hydroxylation step. The obtained results demonstrate that CYP21 and to a lesser extent also CYP3A4 expressing strains can catalyze this steroid hydroxylation. Subsequent 5 l-scale fermentation resulted in the production and purification of 10 mg of metabolite and its unequivocal structure determination via NMR. The synthesis of this urinary metandienone metabolite via S. pombe-based whole-cell biotransformation now allows its use as a reference substance in doping control assays. by Walter de Gruyter.