Durabolin,Organon,US,1959
An anabolic steroid.
Controlled substance (anabolic steroid)
ChEBI: A 3-oxo Delta4-steroid that is estr-4-en-3-one substituted by a beta-hydroxy group at position 17.
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.
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.
Experimental reproductiveeffects. When heated to decomposition it emits acridsmoke and irritating fumes.
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.
