89685-22-3

Usage

Uses

Used in Scientific Research:
5ALPHA-ANDROSTAN-3ALPHA-OL-17-ONE-16,16-D2 is used as a research compound for studying the biological activity and metabolic pathways of androstanolone and its analogs. The isotopic labeling allows for easier tracking and detection of the compound in complex biological systems, providing valuable insights into its interactions with enzymes, receptors, and other biomolecules.
Used in Drug Development:
In the pharmaceutical industry, 5ALPHA-ANDROSTAN-3ALPHA-OL-17-ONE-16,16-D2 serves as a valuable tool in the development of new drugs targeting the androstanolone pathway. Its stable isotopic labeling enables researchers to monitor the compound's pharmacokinetics, pharmacodynamics, and potential side effects, aiding in the optimization of drug candidates and their therapeutic efficacy.
Used in Metabolomics Studies:
5ALPHA-ANDROSTAN-3ALPHA-OL-17-ONE-16,16-D2 is utilized in metabolomics research to investigate the role of androstanolone in various metabolic processes. The isotopic labeling allows for the differentiation between endogenous and exogenous sources of the compound, providing a clearer understanding of its metabolic fate and potential impact on health and disease.
Used in Analytical Chemistry:
In the field of analytical chemistry, 5ALPHA-ANDROSTAN-3ALPHA-OL-17-ONE-16,16-D2 is employed as an internal standard or reference material for the accurate quantification and identification of androstanolone and related compounds in various samples. Its stable isotopic labeling ensures reliable and reproducible results, improving the accuracy and precision of analytical methods.
Used in Sports Doping Control:
5ALPHA-ANDROSTAN-3ALPHA-OL-17-ONE-16,16-D2 can be used in anti-doping research and testing to detect the abuse of androstanolone and its analogs in athletes. The isotopic labeling allows for the differentiation between natural and synthetic sources of the compound, helping to identify potential cases of doping and maintain fair competition in sports.

Upstream product

• 53-41-8 cis-androsterone 

Downstream Products

• 79037-33-5 5α-<16,16,17-²H3>androstane-3α,17β-diol 
• 79037-32-4 <16,16,17-2H3>Androstane-3α,17β-diol 

Relevant academic research and scientific papers

Organocatalytic Deuteration Induced by the Dynamic Covalent Interaction of Imidazolium Cations with Ketones

In this article, we suggest a new organocatalytic approach based on the dynamic covalent interaction of imidazolium cations with ketones. A reaction of N-alkyl imidazolium salts with acetone-d6 in the presence of oxygenated bases generates a dynamic organocatalytic system with a mixture of protonated carbene/ketone adducts acting as H/D exchange catalysts. The developed methodology of the pH-dependent deuteration showed high selectivity of labeling and good chiral functional group tolerance. Here we report a unique methodology for efficient metal-free deuteration, which enables labeling of various types of α-acidic compounds without trace metal contamination. (Figure presented.).

Synthesis of deuterium-labeled 5α-androstane-3α,17β-diol and its 17β-glucuronide

Using unlabeled androsterone as starting material, 5α-[16,16-2H2]androstan-3α-ol-17-one was synthesized by exchange using deuterated potassium methoxide. This labeled androsterone product was reduced by sodium borodeuteride, which gave predominantly trideuterated 5α-androstane-3α,17β-diol. The labeled androstanediol was conjugated with glucuronide by using the Koenig-Knorr reaction with methyl-1-bromo-1-deoxy-2,3,4-tri-O-acetyl-α-D-glucopyranosuronate. The dominant product was identifed by thermospray high-performance liquid chromatography/mass spectrometry (MS) and electrospray MS as 5α-[16,16,17-2H3]androstane-3α,17β-diol,17β-glucuronide.

Application of Gas Chromatography/Mass Spectrometry to Steroid Analysis in Equine Sports: Problems with Enzyme Hydrolysis

In steroid analysis in biological fluids, cleavage of conjugates is an essential step which can be achieved by either enzymatic or chemical hydrolysis.Where conjugation with both glucuronic acid and sulphate occurs, then the use of the enzyme preparation from Helix pomatia, containing both β-glucuronidase and aryl sulphatase activities, would appear to be advantageous.However, it has been shown that the sulphatase enzymes of Helix pomatia do not hydrolyse 17β-sulphates and that other enzymatic activities also present in the preparation can give rise to artefact formation with certain steroids.The artefacts produced from incubation of dehydroisoandrosterone with the enzyme preparation from Helix pomatia have been identified by gas chromatography/mass spectrometry (GC/MS) as androst-4-ene-3,17-dione, androsta-4,6-diene-3,17-dione, androst-4-ene-3,6,17-trione and 6-hydroxyandrost-4-ene-3,17-dione.Incubation of androst-5-ene-3,17-diol produced a similar series of compounds with a 17-hydroxy function.Semi-quantitative GC/MS analysis has been used to determine the extent of these transformations in the presence of increasing amounts of the Helix pomatia preparation.Quantitative conversion in buffer can be obtained but the results from incubation in urine showed a marked modifying effect with minimal artefact formation.The enzyme preparation from Escherichia coli does not yield any artefacts and results are presented for the optimization of its use in the hydrolysis of the glucuronic acid conjugate of 5α-estrane-3β,17α-diol, the major metabolite of mandrolone in the horse.