912291-78-2

Usage

Uses

Used in Anti-Doping Applications:
17β-HydroxyMethyl-17α-Methyl-18-norandrosta-1,4,13-trien-3-one is used as a biomarker for detecting the presence of Metandienone in urine samples. This metabolite can be detected up to 19 days after the administration of Metandienone, making it a valuable tool in anti-doping efforts to identify and penalize athletes who use this banned substance to enhance their performance.
Used in Sports Medicine Research:
In the field of sports medicine, 17β-HydroxyMethyl-17α-Methyl-18-norandrosta-1,4,13-trien-3-one serves as a research subject to better understand the metabolism and excretion patterns of anabolic steroids. This knowledge can help develop more effective testing methods and strategies to combat doping in sports.
Used in Pharmaceutical Industry:
17β-HydroxyMethyl-17α-Methyl-18-norandrosta-1,4,13-trien-3-one may also be used in the pharmaceutical industry for the development of new drugs and therapies targeting muscle growth and strength. Understanding the metabolic pathways and effects of 17β-HydroxyMethyl-17α-Methyl-18-norandrosta-1,4,13-trien-3-one can provide insights into the potential therapeutic applications of similar compounds in treating conditions such as muscle wasting diseases or muscle atrophy.

Upstream product

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

Relevant academic research and scientific papers

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.

C?H Acetoxylation-Based Chemical Synthesis of 17 β-Hydroxymethyl-17 α-methyl-18-norandrost-13-ene Steroids

Palladium-catalyzed C?H acetoxylation has been proposed as a key transformation in the first chemical synthesis of steroids bearing a unique 17β-hydroxymethyl-17α-methyl-18-nor-13-ene D-fragment. This C?H functionalization step was crucial for inverting the configuration at the quaternary stereocenter of a readily available synthetic intermediate. The developed approach was applied to prepare the metandienone metabolite needed as a reference substance in anti-doping analysis to control the abuse of this androgenic anabolic steroid.

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.