58-18-4

Methyltestosterone, also known as 17α-methyltestosterone or as 17α-methylandrost-4-en-17β-ol-3-one, a synthetic derivative of testosterone, is an androgen and anabolic steroid (AAS) medication. It is mainly used in the treatment of low testosterone levels in men, delayed puberty in boys, at low doses as a component of menopausal hormone therapy for menopausal symptoms like hot flashes, osteoporosis, and low sexual desire in women, and to treat breast cancer in women (1-3). 17α-methyltestosterone (MT) is an exogenous anabolic steroid hormone used widely in aquafarming. It has been used in the treatment of various symptoms such as hypogonadism, cryptorchidism, delayed puberty, and erectile dysfunction in males, and in low doses to treat menopausal symptoms (specifically for osteoporosis, hot flashes, and to increase libido and energy), postpartum breast pain and engorgement. In US, 17-Methyltestosterone is an anabolic steroid hormone that majorly used to treat men with a testosterone deficiency, hypogonadism and delayed puberty. For the treatment of women breast cancer, the dosage of 17-Methyltestosterone in females is from 50-200 mg daily.

Warning and precaution

People of the following cases should not use it: allergy; prostate cancer; male breast cancer, pregnant. People with liver or kidney disease, an enlarged prostate, heart disease, congestive heart failure should use with caution.

Definition

ChEBI: A 17beta-hydroxy steroid that is testosterone bearing a methyl group at the 17alpha position.

Brand name

Android (Valeant);Metandren (Novartis); Oreton (Schering); Testred (Valeant); Virilon (Star).

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. Human teratogenic effects by ingestion: developmental abnormalities of the urogenital system. Experimental teratogenic and reproductive effects. Human systemic effects: cholestatic jaundce, weight loss or decreased weight gain. Questionable human carcinogen producing liver tumors. A synthetic androgenic steroid. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

Methyltestosterone, 17β-hydroxy-17α-methylandrost-4-en-3-one (29.1.7), is also synthesized from androstenolone by reacting it with methylmagnesiumiodide, forming the corresponding tertiary alcohol (29.1.6), and subsequent oxidation of the hydroxyl group at C3 to a ketone using chromium (VI) oxide. Simultaneous isomerization of the double bond takes place under the reaction conditions, giving the desired methyltestosterone (29.1.7).

InChI:InChI=1/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1