3704-09-4

Basic information

• Product Name: Mibolerone
• Synonyms: 17-HYDROXY-7,17-DIMETHYL-ESTR-4-EN-3-ONE;17BETA-HYDROXY-7ALPHA,17-DIMETHYLESTR-4-EN-3-ONE;4-ESTREN-7-ALPHA, 17-ALPHA-DIMETHYL-17-BETA-OL-3-ONE;7a,17a-dimethyl-19-nortestosterone;MIBOLERONE;U-10997;17-beta-hydroxy-7-alpha,17-dimethyl-estr-4-en-3-on;17-hydroxy-7,17-dimethyl-,(7-alpha,17-beta)-estr-4-en-3-on
• CAS NO: 3704-09-4
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.45
• EINECS: 223-046-5
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Steroid and Hormone
• Mol File: 3704-09-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 168-171°C
• Boiling Point: 383.47°C (rough estimate)
• Flash Point: 187.787 °C
• Appearance: white crystalline solid
• Density: 1.0434 (rough estimate)
• Vapor Pressure: 1.31E-09mmHg at 25°C
• Refractive Index: 1.4980 (estimate)
• Storage Temp.: Controlled Substance, -20?C Freezer
• PKA: 15.13±0.60(Predicted)
• CAS DataBase Reference: Mibolerone(CAS DataBase Reference)
• NIST Chemistry Reference: Mibolerone(3704-09-4)
• EPA Substance Registry System: Mibolerone(3704-09-4)

Safety Data

• Hazard Codes: T
• Statements: 60-63
• Safety Statements: 36-45
• Hazardous Substances Data: 3704-09-4(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

Synthetic anabolic steroid related to testosterone. Controlled substance (anabolic steroid)

Definition

ChEBI: An androgen that is nalandrone carrying two methyl substituents at positions 7alpha and 17.

Safety Profile

Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.

Veterinary Drugs and Treatments

Cheque? Drops was labeled as indicated “for estrous (heat) prevention in adult female dogs not intended primarily for breeding purposes.” In clinical trials it was 90% effective in suppressing estrus. Although not approved, mibolerone at dosages of 50 micrograms per day will prevent estrus in the cat, but its use is generally not recommended because of the very narrow therapeutic index of the drug in this species (see the Adverse Effects and Overdosage sections for more information).

InChI:InChI=1/C20H30O2/c1-12-10-13-11-14(21)4-5-15(13)16-6-8-19(2)17(18(12)16)7-9-20(19,3)22/h11-12,15-18,22H,4-10H2,1-3H3/t12-,15+,16-,17+,18-,19+,20+/m1/s1

Synthetic route

mibolerone (3704-09-4) → (7R,8R,9R,10R)-7,17,17-Trimethyl-1,2,6,7,8,9,10,11,12,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one

Conditions	Yield
With hydrogenchloride

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide (24589-78-4) + mibolerone (3704-09-4) → C26H46O2Si2 (1202644-40-3)

Conditions	Yield
With ammonium iodide; 2-hydroxyethanethiol at 60℃; for 0.333333h;
With ammonium iodide; ethanethiol In acetonitrile at 80℃; for 0.5h;

Relevant articles and documents

ANDROGEN AS A MALE CONTRACEPTIVE AND NON-CONTRACEPTIVE ANDROGEN REPLACEMENT

The present invention relates to methods of providing male contraception using a specified androgen without the need of a separate sterilizing agent. The invention also describes methods for non-contraceptive androgen replacement and devices useful for carrying out both processes.

Method for androgen supplementation

A particular group of androgens is not metabolized to their 5α-reduced form in the prostate and other tissues. Thus, administration of these compounds--testosterone derivatives with a non-hydrogen substituent in the 6α or 7α position--allows one to provide androgen supplementation therapy without stimulating abnormal prostate growth. A preferred compound for use in the invention is 7α-methyl-19-nortestosterone.