Nandrolone

Chemical Properties

Crystalline Solid

Originator

Durabolin,Organon,US,1959

Uses

An anabolic steroid. Controlled substance (anabolic steroid)

Definition

ChEBI: A 3-oxo Delta4-steroid that is estr-4-en-3-one substituted by a beta-hydroxy group at position 17.

Manufacturing Process

An ice-cold solution of 1.5 grams of 19-nortestosterone and 1.5 ml of dry pyridine in 10 ml of dry benzene is prepared and a solution of 1.5 ml of β- phenylpropionyl chloride in 5 ml of dry benzene is added dropwise over a period of about 2 minutes with stirring. The resulting mixture is allowed to stand overnight under an atmosphere of nitrogen and then washed successively with cold 5% aqueous hydrochloric acid solution, cold 2.5% aqueous sodium hydroxide solution, and water. After drying over anhydrous sodium sulfate, the solvent is evaporated to give an almost colorless oil. Recrystallization from methanol gives white crystals of 19-nortestosterone 17- β-phenylpropionate, MP 91° to 92.5°C.

Therapeutic Function

Anabolic

Mechanism of action

Nandrolone facilitates formation of body muscle mass and strengthens the process of osseous tissue development. The main indications for using nandrolone, as well as other anabolic steroids, are abnormal protein anabolism, asthenia, diseases accompanied by protein loss, adrenal insufficiency, steroid diabetes, and prolonged condition of sluggishness.

Safety Profile

Experimental reproductiveeffects. When heated to decomposition it emits acridsmoke and irritating fumes.

Synthesis

Nandrolone, 17|-hydroxyester-4-en-3-one (29.1.7), is made from estradiol (28.1.17). The phenol hydroxyl group undergoes methylation by dimethylsulfate in the presence of sodium hydroxide, forming the corresponding methyl ether (29.3.1), and then the aromatic ring is reduced by lithium in liquid ammonia, which forms an enol ether (29.3.2). Hydrolyzing this compound with a mixture of hydrochloric and acetic acids leads to the formation of a keto group, and simultaneous isomerization of the double bond from C5¨CC10 to position C4¨CC5 gives the desired nandrolone (29.3.3) [16¨C19]. Upon necessity of using it in the form of acid esters, the product is acylated by corresponding acid derivatives.