14531-84-1

Usage

Uses

Used in Medical Applications:
6-Dehydronandrolone is used as a therapeutic agent for the treatment of muscle-wasting diseases, where it aids in the growth and development of muscles and bones. Its anabolic effects are beneficial for patients suffering from conditions that result in muscle atrophy and reduced bone density.
Used in Sports Performance Enhancement:
Although its use is controversial and often prohibited, 6-Dehydronandrolone is sometimes used as a performance-enhancing drug in sports. Athletes may misuse this AAS to increase muscle mass, strength, and endurance, which can provide a competitive advantage. However, this use is associated with significant health risks and is subject to strict regulations and bans in professional sports.
Used in Research and Development:
6-Dehydronandrolone is utilized in scientific research to study the effects of anabolic-androgenic steroids on the human body. Researchers investigate its potential applications in various medical fields, as well as its mechanisms of action and side effects, to develop safer and more effective treatments for conditions that could benefit from its anabolic properties.

InChI:InChI=1/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2,4,10,13-17,20H,3,5-9H2,1H3/t13?,14?,15?,16?,17?,18-/m0/s1

Upstream product

• 434-22-0 19-nortestosterone 
• 118-75-2 chloranil 
• 70286-48-5 3-acetoxy-19-nor-androsta-3,5-dien-17-one 
• 734-32-7 estra-4-ene-3,17-dione 
• 6925-84-4 3-Ethoxy-17β-acetoxy-19-nor-androsta-3,5-dien 
• 2590-41-2 6-dehydro-19-nortestosterone acetate 
• 1425-10-1 19-nortestosterone acetate 

Downstream Products

• 13209-45-5 estra-4,6-diene-3,17-dione 
• 2590-41-2 6-dehydro-19-nortestosterone acetate 

Relevant academic research and scientific papers

Preparation method of 6-dehydronandrolone acetate

The invention belongs to the technical field of steroid drug intermediates, and provides a preparation method of 6-dehydronandrolone acetate. The preparation method comprises the following steps: carrying out a catalytic reaction on estra-4-ene-3,17-dione, acetic anhydride and p-toluenesulfonic acid to obtain a compound 1; carrying out a reduction reaction on the compound 1, hydroboron and aluminum trichloride to obtain a compound 2; subjecting the compound 2 and N-bromosuccinimide to reacting with DMF to obtain a solution of a compound 3; carrying out an addition reaction on the solution of the compound 3 and alkali to obtain a compound 4; and subjecting the compound 4, acetic anhydride, triethylamine and dichloromethane to a catalytic reaction to obtain 6-dehydronandrolone acetate. By adding borohydride and the aluminum trichloride in a reasonable ratio, hydrolysis of a 3-site ester group is effectively avoided, and side reactions are few; and meanwhile, the yield and the purity of a target product are remarkably improved by reasonably setting a synthesis route and controlling a reaction temperature.

Microbial hydroxylation of steroids. 9. Epoxidation of Δ6-3-ketosteroids by Rhizopus arrhizus ATCC 11145, and the mechanism of the 6β hydroxylase enzyme

A series of Δ6-3-ketosteroids has been incubated with the C-6β hydroxylating fungus Rhizopus arrhizus ATCC 11145.Ring A aromatic steroids are not metabolized by this fungus, nor are 3-chloro- and 3-(N-pyrrolideno)-androsta-3,5-dienes. Δ4,6-3-Ketosteroids are epoxidized at the 6,7 position by R. arrhizus with β stereochemistry; in contrast, both 5α- and 5β-Δ6-3-ketosteroids are epoxidized with α stereochemistry by fungal and peracid reagents.The results of this and previous studies now make it possible to define the nature of the hydroxylating/epoxidizing species of the 6β hydroxylase enzyme of R. arrhizus.Evidence is presented for a stepwise reaction mechanism in both cases.Improved methods of synthesis are described for 6-methylene-testosterone and estra-4,6-dien-17β-ol-3-one.

Conversion of Enones into Dienones via Allylpalladium Complexes

A series of reagents for the conversion of enones into dienones via allylpalladium compounds has been studied and mild conditions for dienone preparation are recommended.

3-Keto-7 α,β-loweralkyl-Δ 5-steroids

7(α,β)-Loweralkyl-3-keto-Δ 5 -androstanes and 7(α,β)-loweralkyl-3-keto-Δ 5 -pregnanes having anabolic, androgenic, claudogenic, progestational and anti-progestational properties are prepared by reacting 3-keto-4,6-dienic androstanes and pregnanes with organocopper reagents such as dialkyllithium cuprate. The isomerization of these compounds to yield 7(α,β)-loweralkyl-3-keto-Δ 4 -steroids is also described.