1424-00-6

Basic information

• Product Name: Mesterolone
• Synonyms: Acetonitrile (test Mesterolone, 1.0 mg/mL);Mesterolone (CIII);(1α,5α,17β)-17-hydroxy-1-Methylandrostan-3-one;1α-Methyl-17β-hydroxy-5α-androstan-3-one;1α-Methyl-5α-dihydrotestosterone;NSC 75054;Mesterolone(Proviron);(1S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-1,10,13-triMethyltetradecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
• CAS NO: 1424-00-6
• Molecular Formula: C₂₀H₃₂O₂
• Molecular Weight: 304.47
• EINECS: 215-836-3
• Product Categories: Steroid and Hormone;API;Biochemistry;Hydroxyketosteroids;Steroids
• Mol File: 1424-00-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 208 °C
• Boiling Point: 420.3 °C at 760 mmHg
• Flash Point: 179.4 °C
• Appearance: /
• Density: 1.058 g/cm³
• Vapor Pressure: 7.98E-09mmHg at 25°C
• Refractive Index: 17.6 ° (C=0.9, CHCl3)
• Storage Temp.: 2-8°C
• Solubility: Practically insoluble in water, sparingly soluble in acetone, in ethyl acetate and in methanol
• PKA: 15.09±0.70(Predicted)
• Water Solubility: 3mg/L at 20℃
• Merck: 5916
• CAS DataBase Reference: Mesterolone(CAS DataBase Reference)
• NIST Chemistry Reference: Mesterolone(1424-00-6)
• EPA Substance Registry System: Mesterolone(1424-00-6)

Safety Data

• Hazard Codes: Xn,T,F
• Statements: 20/21/22-38-19-11-61-60
• Safety Statements: 22-24/25-36/37/39-45-53
• WGK Germany: 3
• RTECS: BV8063400
• Hazardous Substances Data: 1424-00-6(Hazardous Substances Data)

Usage

Description

Mesterolone, also known as a synthetic anabolic-androgenic steroid (AAS) and a derivative of dihydrotestosterone (DHT), is a 3-oxo-5alpha-steroid. It is characterized by the addition of a methyl group at the carbon one position, which allows it to survive oral ingestion by protecting it from hepatic breakdown. Mesterolone is considered a weak androgen due to its inactivation by 3α-hydroxysteroid dehydrogenase in skeletal muscles and is not a substrate for aromatase, meaning it is not converted into estrogen. It is available as an analytical reference standard and is regulated as a Schedule III drug in the United States.

Uses

Used in Medical Applications:
Mesterolone is used as a replacement therapy for patients with low testosterone or symptoms of aging male syndrome. Its weak androgenic activity and inability to be aromatized to estrogens make it a suitable choice for such treatments.
Used in Sports Performance Enhancement:
Mesterolone is used as a performance-enhancing drug in sports, aiming to improve athlete performance. Its anabolic and androgenic properties contribute to increased muscle mass and strength, making it a popular choice among athletes.
Used in Research and Forensic Applications:
Mesterolone is used as an active ingredient in various pharmaceutical preparations for research purposes. Its structural properties and effects on the body make it a valuable compound for studying the mechanisms of anabolic and androgenic steroids.
Used in Treatment of Depression:
Experiments are still ongoing to explore the potential use of Mesterolone as a treatment for depression. Its effects on mood and mental health are being investigated, and it may offer a new avenue for therapeutic intervention in the future.
Chemical Properties:
Mesterolone is a white or yellowish crystalline powder, which is an important characteristic for its identification and application in various fields.

Originator

Proviron,Schering,W. Germany,1967

Manufacturing Process

500 mg of 1α-methyl-androstan-17β-ol-3-one-17-acetate are heated under reflux for 90 minutes in a nitrogen atmosphere in 5 ml of 4% methanolic sodium hydroxide solution. The reaction mixture is then stirred into ice water,the precipitated product filtered with suction and recrystallized from isopropyl ether. 1α-Methyl-androstan-17β-ol-3-one melts at 203.5° to 205°C.

Therapeutic Function

Androgen

InChI:InChI=1/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1

Upstream product

• 153-00-4 17β-hydroxy-1-methyl-5α-androst-1-en-3-one 
• 604-26-2 17β-hydroxy-1α-methyl-androst-4-en-3-one 
• 1971-67-1 5α-androst-1-en-3-one-17β-yl benzoate 
• 75-16-1 methylmagnesium bromide 
• 1423-99-0 1α-methyl-5α-androstane-3,17-dione 
• 1057-07-4 stanolone benzoate 

Downstream Products

• 4349-94-4 1α-Methyl-5α-androstan-3α,17β-diol 
• 604-26-2 17β-hydroxy-1α-methyl-androst-4-en-3-one 
• 2881-21-2 1α,17α-Dimethyl-17β-hydroxy-5α-androstan-3-on 

Related news

Clinical and clinical research articleThe effect of Mesterolone (cas 1424-00-6) on sperm count, on serum follicle stimulating hormone, luteinizing hormone, plasma testosterone and outcome in idiopathic oligospermic men09/28/2019

Two hundred fifty subfertile men with idiopathic oligospermia (count less than 20 million/ml) were treated with mesterolone (100–150 mg/day) for 12 months. Seminal analysis were assayed 3 times and serum follicle stimulating hormone (FSH) luteinizing hormone (LH) and plasma testosterone were as...detailed

Biotransformation of androgenic steroid Mesterolone (cas 1424-00-6) with Cunninghamella blakesleeana and Macrophomina phaseolina09/27/2019

Fermentation of mesterolone (1) with Cunninghamella blakesleeana yielded four new metabolites, 1α-methyl-1β,11β,17β-trihydroxy-5α-androstan-3-one (2), 1α-methyl-7α,11β,17β-trihydroxy-5α-androstan-3-one (3), 1α-methyl-1β,6α,17β-trihydroxy-5α-androstan-3-one (4) and 1α-methyl-1β,1...detailed

Metabolic studies of Mesterolone (cas 1424-00-6) in horses09/26/2019

Mesterolone (1α-methyl-5α-androstan-17β-ol-3-one) is a synthetic anabolic androgenic steroid (AAS) with reported abuses in human sports. As for other AAS, mesterolone is also a potential doping agent in equine sports. Metabolic studies on mesterolone have been reported for humans, whereas lit...detailed

Three new analogues of androgenic drug Mesterolone (cas 1424-00-6) through biotransformation with Cunninghamella blakseleeana09/25/2019

Three new metabolites were obtained on incubation of androgenic steroid mesterolone (1) with Cunninghamella blakesleeana. These metabolites were identified as 1α-methyl-11β,14α,17β-trihydroxy-5α-androstan-3-one (2), 1α-methyl-7β,17β-dihydroxy-5α-androstan-3-one (3), and 1α-methyl,17β-...detailed

Relevant articles and documents

USE OF alpha,beta -UNSATURATED CARBONYL COMPOUNDS AS QUENCH REAGENTS FOR THE BIRCH REDUCTION

Use of α,β-unsaturated carbonyl compounds as quench reagents for the Birch reduction.

Process for the preparation of androstane-3,17-dione derivatives

A process for the preparation of androstane-3,17-dione compounds of the formula STR1 wherein X is 1,2-methylene or 1- or 2-methyl, comprises fermenting a sterol of the formula STR2 wherein X is as above and R1 is the hydrocarbon residue of 8-10 carbon atoms, of a sterol, with a microorganism culture capable of effecting the side chain degradation of sterols.