641-82-7

Basic information

• Product Name: 17b-Methyl-5a-androstane-3a,17b-diol
• Synonyms: 17b-methyl-5a-androstane-3a,17b-diol;17-methyl-5alpha-androstan-3alpha,17beta-diol;17alpha-methyl-5alpha-androstan-3alpha,17beta-diol;(3alpha,5beta,17beta)-17-methylandrostane-3,17-diol;17β-Methyl-5α-androstane-3α,17β-diol;(3ALPHA,5ALPHA,17BETA)-17-METHYLANDROSTANE-3,17-DIOL;NSC51177;(3R,5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS NO: 641-82-7
• Molecular Formula: C₂₀H₃₄O₂
• Molecular Weight: 306.48
• Mol File: 641-82-7.mol

Chemical Properties

• Boiling Point: 418.1 °C at 760 mmHg
• Flash Point: 184.4 °C
• Appearance: white crystalline powder
• Density: 1.069
• Vapor Pressure: 9.7E-09mmHg at 25°C
• Refractive Index: 1.537
• PKA: 15.12±0.70(Predicted)
• CAS DataBase Reference: 17b-Methyl-5a-androstane-3a,17b-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 17b-Methyl-5a-androstane-3a,17b-diol(641-82-7)
• EPA Substance Registry System: 17b-Methyl-5a-androstane-3a,17b-diol(641-82-7)

Safety Data

• Hazardous Substances Data: 641-82-7(Hazardous Substances Data)

Usage

Uses

Used in Sports and Bodybuilding:
17b-Methyl-5a-androstane-3a,17b-diol is used as a performance-enhancing supplement by bodybuilders and athletes for the purpose of increasing muscle mass and strength. However, its use is not supported by scientific evidence and is strongly discouraged by health professionals due to its potential dangers.

InChI:InChI=1/C20H34O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h13-17,21-22H,4-12H2,1-3H3/t13-,14+,15+,16-,17-,18-,19-,20-/m0/s1

Upstream product

• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 481-29-8 Epiandrosterone 
• 75-16-1 methylmagnesium bromide 
• 58-18-4 17-methyltestosterone 
• 113466-02-7 Acetic acid (3S,5S,8R,9S,10S,13S,14S,17S)-3-acetoxy-10,13,17-trimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester 
• 521-11-9 mestanolone 
• 71-43-2 benzene 
• 521-10-8 methylandrostenediol 

Downstream Products

• 521-11-9 mestanolone 
• 18167-94-7 5α-17β-hydroxy-17α-methyl-Δ¹-androsten-3-one 
• 58-18-4 17-methyltestosterone 

Relevant articles and documents

Characterization of desoxymethyltestosterone main urinary metabolite produced from cultures of human fresh hepatocytes

Desoxymethyltestosterone (DMT; 17β-hydroxy-17α-methyl-5α- androst-2-ene) is a designer steroid present in hormonal supplements distributed illegally as such or in combination with other steroids, for self-administration. It figures on the list of substances prohibited in sports and its detection in athlete's urine samples is based upon the presence of the parent compound or the main urinary metabolite, which has not been characterized yet. Following its isolation from cultures of human fresh hepatocytes and S9 fractions of liver homogenates, we were able to identify this metabolite as being 17α-methyl-2β,3α,17β-trihydroxy-5α-androstane. Other minor metabolites were also characterized. The production, isolation, NMR, mass spectral analyses and chemical synthesis are presented.

Novel metabolites of dehydroepiandrosterone and progesterone obtained in Didymosphearia igniaria KCH 6670 culture

Dehydroepiandrosterone (DHEA) (10) and its five derivatives: testosterone (1), androstenedione (2), 17α-methyltestosterone (6), progesterone (13) and pregnenolone (14) were subjected to microbial transformation by the filamentous fungus Didymosphaeria igniaria KCH 6670. The predominant metabolism of the incubated 5-ene steroids (10 and 14) occurred through 3β-hydroxy-steroid dehydrogenase/5,4-en isomerase pathways resulting in the generation of a 4-en-3-oxo system on ring-A. The transformations of C 19 steroids (1, 2, and 10) included a hydroxylation at 7α position, ketone-alcohol interconversion at C-17 and reduction of the double bond at C-4 and 3-keto group to the 3β-alcohol with 5α- stereochemistry at A/B ring. D. igniaria also carried out 6(7)-dehydrogenation and 6,7β-epoxidation during transformation of DHEA. Under these conditions transformation of DHEA (10) gave four products: 7α-hydroxyandrost-4-en-3, 17-dione (4), 17β-hydroxyandrost-4,6-dien-3-one (11), 17β- hydroxyandrost-6β-epoxy-4-en-3-one (12) and 3β,17β-dihydroxy- 5α-androstane (5). The compounds 11 and 12 are identified as DHEA metabolites for the first time. The transformation of C21 steroids (13 and 14) led to the mixture of mono- (mainly 11α- and 15β-) and dihydroxy- (7α,15β-; 14α,15β-; 11α,15β-; 11α,14α-) products. 7α,15β-Dihydroxypregnan-4-en-3,20- dione (18) and 14α,15β-dihydroxypregnan-4-en-3,20-dione (19) were found to be new compounds. The main product of transformation of 17α-methyltestosterone (6) was 12β-hydroxy-17α- methyltestosterone (7). The results of these transformations demonstrate the dependence of hydroxylation position on the structure of steroid nucleus.

A convenient synthesis of oxandrolone through a regioselective Candida antarctica lipase-catalyzed transformation

The use of a regioselective CAL-catalyzed transformation of a suitable intermediate allowed a convenient synthesis of oxandrolone, an anabolic hormone actually employed to improve the quality of life for patients with HIV-infections.

TRIS(3,6-DIOXAHEPTYL)AMINE: A SUPERIOR COMPLEXING AGENT FOR DISSOLVING METAL REACTIONS

Commercially available tris(3,6-dioxaheptyl)amine (TDA-1) is an effective phase transfer catalyst for reactions with sodium-potassium alloy in tetrahydrofuran.Deoxygenation of acetates, dehalogenation, and hydrolysis of tosylates and mesylates proceed in high yield.The use of a deuterated alcohol during deoxygenation reactions leads to site-specific deuteration.

Proton magnetic resonance spectra of 17ξ-hydroxy-17ξ-methyl-5ξ-androstane C-3 ketone and C-3ξ alcohol isomers in chloroform-d and pyridine-d5

17α-Hydroxy-17β-methyl-5β-androstan-3-one,17β-methyl-5α-androstane-3α ,17α-diol,17β-methyl-5α-androstane-3β,17α-diol, 17α-methyl-5β-androstane-3β,17β-diol,17β-methyl-5β-androstane- 3α,17α-diol and 17β-methyl-5β-androstane-3β,17α-diol were synthesized for the first time. 1H NMR spectra of all four 17ξ-hydroxy/17ξ-methyl C-3 ketones and all eight C-3 alcohols were recorded in chloroform-d and pyridine-d5. Pyridine-induced chemical shifts are discussed. Thin-layer chromatographic data are given.

METABOLISM OF 17α-METHYLTESTOSTERONE IN THE RABBIT: C-6 and C-16 HYDROXYLATED METABOLITES

17α-Methyltestosterone and the reduced metabolites, 17α-methyl-5α-androstane-3α,17β-diol, 17α-methyl-5α-androstane-3β,17β-diol and 17α-methyl-5β-androstane-3α,17β-diol, together with three hydroxylated metabolites, 17α-methyl-5β-androstane-3α,16α,17β-triol, 17α-methyl-5β-androstane-3α,16β,17β-triol and a new metabolite, 17α-methyl-5α-androstane-3β,6α,17β-triol, were isolated and identified in the urine of rabbits dosed with 17α-methyltestosterone.No hydroxylated 5α-metabolite of 17α-methyltestosterone has been identified previously.No evidence for epimerization at the C-17 position was observed.

Microbiological Transformations. XVI. Transformation of 5α- and 5β-Dihydro, and 1- and 6-Dehydro Derivatives of Testosterone and Androstenedione by Means of Rhodotorula mucilaginosa Strain

The following transformation of 5α- and 5β-dihydro derivatives of testosterone and androstenedione by means of Rhodotorula mucilaginosa has been observed: reduction of the carbonyl group on C-3 to both possible alcohols in the 5α-series and only to one alcohol (3α) in the 5β-series.In the transformation of 1- and 6-dehydro derivatives of testosterone and androstenedione, reduction in ring A was completely inhibited.The carbonyl or hydroxy groups at C-17 in both series of substrates underwent interconversion.