641-84-9

Basic information

• Product Name: 17α-Methyl-5β-androstane-3α,17β-diol
• Synonyms: (3R,5R,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: 641-84-9
• Molecular Formula: C₂₀H₃₄O₂
• Molecular Weight: 306.48276
• Mol File: 641-84-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 418.1°Cat760mmHg
• Flash Point: 184.5°C
• Appearance: /
• Density: 1.069g/cm³
• Vapor Pressure: 9.7E-09mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: 17α-Methyl-5β-androstane-3α,17β-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 17α-Methyl-5β-androstane-3α,17β-diol(641-84-9)
• EPA Substance Registry System: 17α-Methyl-5β-androstane-3α,17β-diol(641-84-9)

Safety Data

• Hazardous Substances Data: 641-84-9(Hazardous Substances Data)

Usage

Type

Synthetic androgen and anabolic steroid

Derivative of

Testosterone

Modification

Methyl group added to the 17α position

Potency

More potent than testosterone

Resistance

Resistant to breakdown by the liver

Use

Often used in bodybuilding and athletics to increase muscle mass and strength

Approval

Not approved for medical use in the United States

Availability

Sometimes sold as a dietary supplement

Prohibition

Banned by many sports organizations and classified as a prohibited substance

Long-term effects

Can have harmful effects on the liver and cardiovascular system, and can lead to hormonal imbalances and other negative health consequences.

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+/m1/s1

Upstream product

• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 481-29-8 Epiandrosterone 
• 58-18-4 17-methyltestosterone 
• 521-10-8 methylandrostenediol 
• 71-43-2 benzene 
• 521-11-9 mestanolone 
• 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 
• 75-16-1 methylmagnesium bromide 
• 3275-58-9 17β-hydroxy-17α-methyl-5β-androstan-3-one 

Downstream Products

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

Relevant articles and documents

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.

Metabolism of 17α-methyl-5β-dihydrotestosterone in the rabbit

17α-Methyl-5β-androstane-3α,17β-diol together with the hydroxylated metabolites 17α-methyl-5β-androstane-1β,3α,17β-triol, 17α-methyl-5β-androstane-3α,12β,17β-triol, 17α-methyl-5β-androstane-3α,16α,17β-triol and 17α-methyl-5β-androstane-3α,16β,17β-triol were isolated and identified in the urine of rabbits orally dosed with 17α-methyl-5β-dihydrotestosterone. Biotransformations differ from the 5α-series where hydroxylation occurred at C-6 and C-15. In both series, the C-3 equatorial epimer was the major urinary excretion product among the non-hydroxylated metabolites. The 5β-compound was more resistant to metabolic hydroxylation than the 5α-compound. No evidence for epimerization at the C-17 position was observed.