521-11-9

Basic information

• Product Name: Mestanolone
• Synonyms: METHYLDIHYDROTESTOSTERONE;MESTALINE;MESTANOLONE;METHYLANDROSTANOLONE;3-KETO-17B-HYDROXY-17A-METHYL-5A-ANDROSTANE;5ALPHA-ANDROSTANE-17ALPHA-METHYL-17BETA-OL-3-ONE;5-ALPHA-ANDROSTAN-17-ALPHA-METHYL-17-BETA-OL-3-ONE;17ALPHA-METHYLDIHYDROTESTOSTERONE
• CAS NO: 521-11-9
• Molecular Formula: C₂₀H₃₂O₂
• Molecular Weight: 304.47
• EINECS: 208-302-6
• Product Categories: Steroids;Biochemistry;Hydroxyketosteroids;Intermediates & Fine Chemicals;Pharmaceuticals;Steroid and Hormone;API;pharmaceutical intermediate and medicine grade
• Mol File: 521-11-9.mol

Chemical Properties

• Melting Point: 191 °C
• Boiling Point: 385.28°C (rough estimate)
• Flash Point: 177.6 °C
• Appearance: White Solid
• Density: 1.0279 (rough estimate)
• Vapor Pressure: 1.16E-08mmHg at 25°C
• Refractive Index: 1.4824 (estimate)
• Storage Temp.: Controlled Substance, -20?C Freezer
• PKA: 15.15±0.60(Predicted)
• Merck: 5915
• CAS DataBase Reference: Mestanolone(CAS DataBase Reference)
• NIST Chemistry Reference: Mestanolone(521-11-9)
• EPA Substance Registry System: Mestanolone(521-11-9)

Safety Data

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36
• WGK Germany: 3
• RTECS: BV8064500
• Hazardous Substances Data: 521-11-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Mestanolone is used as a pharmaceutical agent for the treatment of male hypogonadism and decreased sperm infertility. Its anabolic and androgenic properties make it effective in addressing these conditions.
Used in Sports and Bodybuilding:
Mestanolone is used as a performance-enhancing drug in sports and bodybuilding. It is favored for its ability to increase strength, lean muscle mass, and improve focus and drive, which can contribute to improved athletic performance and physique development.
Used in Research and Development:
Mestanolone is also used in research and development for studying the effects of anabolic-androgenic steroids on the human body, as well as for developing new treatments for various medical conditions related to androgen deficiency or muscle wasting.

Purification Methods

Dissolve mestanolone in Et2O, wash it with N NaOH, H2O, dry it (Na2SO4), evaporate and recrystallise it from EtOAc. The semicarbazone has m 235-236o (from EtOH). [Ruzicka et al. Helv Chim Acta 18 1487 1935.]

References

https://en.wikipedia.org/wiki/Mestanolone https://en.wikipedia.org/wiki/Dihydrotestosterone#Medical_use http://www.biopharmchem.com/raw-hormone-ermalone-oral-steroid-mestanolone-p01138p1.html

InChI:InChI=1/C20H32O2/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/h13,15-17,22H,4-12H2,1-3H3/t13-,15?,16?,17-,18?,19?,20+/m0/s1

Upstream product

• 641-82-7 17-methyl-5α-androstane-3α,17β-diol 
• 641-82-7 ZIN⁽²²³⁾C₀₅₄₅₁ 
• 58-18-4 17-methyltestosterone 
• 64-19-7 acetic acid 
• 481-29-8 Epiandrosterone 
• 3275-64-7 17β-hydroxy-17α-methyl-5α-androst-2-ene 
• 63-05-8 Androstenedione 
• 972-46-3 3-ethoxyandrosta-3,5-dien-17-one 
• 75245-99-7 5α-androst-17α-methyl-17β-hydroxy-3-ethylene ketal 
• 74-87-3 methylene chloride 
• 74-83-9 methyl bromide 
• 74-88-4 methyl iodide 

Downstream Products

• 53-39-4 oxandrolone 
• 88843-11-2 (5S,8R,9S,10S,13S,14S,17S)-17-Hydroxy-10,13,17-trimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthrene-2-carboxylic acid 
• 641-82-7 17-methyl-5α-androstane-3α,17β-diol 
• 641-82-7 ZIN⁽²²³⁾C₀₅₄₅₁ 
• 18167-94-7 5α-17β-hydroxy-17α-methyl-Δ¹-androsten-3-one 
• 53-39-4 oxandrolone 
• 5781-69-1 17β-Hydroxy-17α-methyl-androstano<2,3-c>furazan-N-oxyd 
• 1239-29-8 Frazalon 
• 3662-93-9 17α-methyl-17β-(3-phenyl-propionyloxy)-(5α)-androstano[2,3-c][1,2,5]oxadiazole 

Relevant articles and documents

A [...] intermediate androst - 17 α - methyl - 17 β - hydroxy -3 - ketone (by machine translation)

The present invention provides a [...] intermediate androst - 17 α - methyl - 17 β - hydroxy - 3 - ketone synthesis method, the method is to 4 - androstenedione (abbreviated as 4 AD) as raw materials, through the 3 position alkone pyridynyl alkylene ether, 17 [...] addition; then in Grignard addition after acid hydrolysis is not carried out in advance 5 at the catalytic hydrogenation reaction of the olefinic bond, then do the 3 bit ether with the 17 bit dual-hydrolysis preparation to obtain compound androst - 17 α - methyl - 17 β - hydroxy - 3 - one, HPLC purity 99.0% or more. The method of the invention route is brief, the production process is easy to control, environmental friendly, low production cost, is suitable for industrial scale production. (by machine translation)

Preparation method of androstane-17alpha-methyl-17beta-hydroxy-3-ketone

The invention provides a preparation method of androstane-17alpha-methyl-17beta-hydroxy-3-ketone. According to the method, methyltestosterone as a raw material is subjected to ketalation, catalytic hydrogenation and a hydrolysis reaction to obtain the androstane-17alpha-methyl-17beta-hydroxy-3-ketone. The method has the advantages that the process is simple and clear, the production cost is low, the purity of the product is high, and the method is suitable for industrial production.

Preparation method of mestanolone

The invention relates to a preparation method of mestanolone. The preparation method comprises the following steps of adopting 4AD as a raw material, carrying out acid catalyzed reaction on the 4AD and triethyl orthoformate in an organic solvent such as lower alcohol to obtain etherate; carrying out grignard addition reaction on the etherate and a methyl-grignard-reagent in an organic solvent to obtain grignard which is 3-ethyoxyl-17a methyl-androstane-3,5-diene-17-alcohol; then catalyzing through palladium-charcoal, carrying out double-bond hydrogenation on a grignard 5 bit to obtain hydride which is 3-ethyoxyl-androstane-3 alkene-17-ketone, finally carrying out acid-catalyzed hydrolysis on the hydride in the organic solvent such as lower alcohol to obtain a mestanolone crude product, and then carrying out decoloration refining through ethyl alcohol and activated carbon to obtain the mestanolone. The HPLC content is 99.5 percent or more, the melting point is 192.5 to 194.0 DEG C, and the synthesis weight total yield is 76 to 83 percent. The preparation method provided by the invention is cheap and easily available in raw materials, simple and convenient in process operation, good in product purity, high in yield, high in solvent recovery rate, reduced in production cost by 25 to 30 percent, and favorable for industrial production.

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.

Efficient oxidizing methods for the synthesis of oxandrolone intermediates

Mild, efficient and eco-friendly oxidation of 17α-methylandrostan- 3β-17β-diol (1) has been studied with three different reagents viz. pentavalent iodine reagent 2-iodoxy benzoic acid (IBX) in DMSO at 65°C, sodium hypochlorite and H2O2/Na2WO4 under phase transfer conditions to give 17β-hydroxy-17α- methylandrostan-3-one (mestanolone 2), a drug intermediate as oxidized product. The H2O2/Na2WO4/PTC gave mestanolone in high yield and purity whereas sodium hypochlorite/PTC system yielded some chlorinated material along with the mestanolone. However, 1 with 2.5 equivalent of IBX gave 17β-hydroxy-17α-methyl- Δ1-androsten-3- one (3) under the similar reaction conditions in good yield and single step reaction.

IBX in an ionic liquid: Eco-friendly oxidation of 17α- methylandrostan-3β,17β-diol, an intermediate in the synthesis of anabolic oxandrolone

An easily available hypervalent iodine(V) reagent, 2-iodoxybenzoic acid (IBX) immobilized in the ionic liquid [bmim][Br] was found to be an efficient and eco-friendly protocol for the oxidation of 17α-methylandrostan- 3β,17β-diol (1). At ambient temperature oxidation of 1 with IBX gave mestanolone (2) in good yield and with an increased stoichiometric amount of IBX, oxidation adjacent to the carbonyl functionality (α,β- unsaturation) occurred to give dehydrogenated 17β-hydroxy-17α-methyl- Δ1-androsten-3-one (3) as the major product in a one-pot reaction. The product is easily obtained by extraction with diethyl ether and evaporation of the solvent.

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.