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
• Article Data: 8

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

General Description

17b-Methyl-5a-androstane-3a,17b-diol, also known as Methyl-1-AD, is an androgen and anabolic steroid which has been used as a performance-enhancing supplement. It is a synthetic derivative of testosterone that is not approved for medical use. 17b-Methyl-5a-androstane-3a,17b-diol is classified as a controlled substance in many countries due to its potential for abuse and the risks associated with its use, including liver toxicity and negative effects on cardiovascular health. Methyl-1-AD is typically used by bodybuilders and athletes looking to increase muscle mass and strength, but 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

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

Downstream Products

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

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-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.