Metenolone

Originator

Primobolan ,Schering ,W. Germany,1961

The Uses of Metenolone

Methenolone is an anabolic steroid. This is a controlled substance.

Definition

ChEBI: Methenolone is a 3-hydroxy steroid. It has a role as an androgen.

Manufacturing Process

8.42 ml of methyl iodide are slowly added dropwise at room temperature with stirring in a nitrogen atmosphere to 3.067 g of magnesium turnings and 107 ml of absolute ether. After about 30 minutes, 185 ml of absolute tetrahydrofuran are slowly introduced and then liquid is distilled off until a boiling point of 62°C is reached. After cooling to room temperature, 613 mg of cuprous chloride are added and then 10 g of ?1,4,6-androstatrien-17β-ol-3- one-17-acetate in 110 ml of tetrahydrofuran slowly introduced. After 30 minutes reaction time, the whole is cooled to 0C, the excess of Grignard reagent decomposed with saturated ammonium chloride solution, the product diluted with ether and the aqueous phase separated. The ethereal phase is washed consecutively with aqueous sodium thiosulfate solution, saturated ammonium chloride solution and water. It is dried over sodium sulfate and evaporated to dryness under vacuum. The residue is dissolved in 40 ml of pyridine and 20 ml of acetic anhydride and the solution kept for 16 hours at room temperature. It is then stirred into ice water and the precipitate filtered with suction, dried and recrystallized from isopropyl ether. 1α-Methyl-?4,6- androstadien-17β-ol-3-one-17-acetate is obtained. MP 156°C to 157°C; [α]D25 = -33.8° (in CHCl3; c = 0.9). Yield 65-70% of the theoretical.
4.67 g of 1α-methyl-?4,6-androstadien-17β-ol-3-one-17-acetate are dissolved in 273 ml of methanol and, after the addition of 350 mg of 10% palladium on calcium carbonate catalyst, hydrogenated until 1 mol equivalent of hydrogen has been taken up. After filtering off the catalyst, the solution is treated with 150 ml of 2N-hydrochloric acid and evaporated under vacuum to about 1/3 of the volume. The whole is then diluted with water and extracted with ether. The ethereal solution is washed with water until neutral, dried over sodium sulfate and evaporated. The crude product is heated on a steam bath for 90 minutes in 10 ml of pyridine and 10 ml of acetic anhydride. Extraction with ether is then carried out and the ethereal phase washed until neutral with water. The crude crystalline 1α-methyl-?4-androsten-17β-ol-3-one-17- acetateobtained after drying and evaporation of the solution, melts at 122°C to 129°C. Yield 98% of the theoretical.
1α-Methyl-?4-androsten-17β-ol-3-one-17-acetate when purified by recrystallization from isopropyl ether melts at 138°C to 139°C.

Therapeutic Function

17β-Hydroxy-1β-methyl-5α-androst-l-ene-3-one acetate