Mestanolone
Mestanolone, also known as methylandrostanolone and sold under the brand names Androstalone and Ermalone among others, is an androgen and anabolic steroid medication which is mostly no longer used. It is still available for use in Japan however. It is taken by mouth.
Side effects of mestanolone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause liver damage. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor, the biological target of androgens like testosterone and dihydrotestosterone. It has strong androgenic effects and weak anabolic effects, which make it useful for producing masculine psychological and behavioral effects. The drug has no estrogenic effects.
Mestanolone was discovered in 1935 and was introduced for medical use in the 1950s. In addition to its medical use, mestanolone has been used to improve physique and performance. It was used in East Germany in Olympic athletes as part of a state-sponsored doping program in the 1970s and 1980s. The drug is a controlled substance in many countries and so non-medical use is generally illicit.
Medical uses
Available forms
Mestanolone was available in the form of 25 mg sublingual tablets.Side effects
s of mestanolone include virilization and hepatotoxicity among others.Pharmacology
Pharmacodynamics
Mestanolone is an AAS, with both androgenic and anabolic effects. It is very similar in its effects to androstanolone, and can be thought of as an orally active version of this AAS. Due to inactivation by 3α-hydroxysteroid dehydrogenase in skeletal muscle, mestanolone is described as a very poor anabolic agent, similarly to androstanolone and mesterolone. As mestanolone is 5α-reduced, it cannot be aromatized and hence has no propensity for estrogenic side effects such as gynecomastia. The drug also has no progestogenic activity. Like other 17α-alkylated AAS, mestanolone is hepatotoxic.Pharmacokinetics
Due to its C17α methyl group, unlike androstanolone, mestanolone is orally active.Chemistry
Mestanolone, also known as 17α-methyl-4,5α-dihydrotestosterone or as 17α-methyl-5α-androstan-17β-ol-3-one, is a synthetic androstane steroid and a 17α-alkylated derivative of dihydrotestosterone. It differs from DHT only by the presence of the methyl group at the C17α position. Close synthetic relatives of mestanolone include oxandrolone, oxymetholone, and stanozolol.Synthesis
The chemical synthesis of mestanolone was reported: Although the Lednicer book method uses DHEA as the starting material, androstenedione is cheaper and more readily available.The reaction of Androstenedione with triethyl orthoformate convers the enone into the corresponding enol ether, 3-Ethoxyandrosta-3,5-dien-17-one . Grignard addition of methyl magnesium halide gives. Catalytic hydrogenation reduces the C5=C6 olefin giving. Hydrolysis of the product in aqueous acid completed the synthesis of mestanolone.