Compound: mestanolone
SMILES: O=C1C[C@H]2[C@]([C@@H]3[C@H]([C@H]4[C@]([C@](O)(C)CC4)(C)CC3)CC2)(C)CC1
InChIKey: WYZDXEKUWRCKOB-YDSAWKJFSA-N
Synonyms: mestanolone, 521-11-9, Assimil, Methybol, Tantarone, Mesanolon, Mestanolona, Mestanolonum, DTXSID0048973, NSC-18219, 17alpha-methylandrostan-3-on-17beta-ol, S712YZ168E, 17beta-Hydroxy-17alpha-methyl-3-androstanone, 17beta-Hydroxy-17-methyl-androstan-3-one, DTXCID3028899, 17alpha-Methylandrostan-17beta-ol-3-one, RefChem:811179, 208-302-6, Methylantalon, Andoron, Ermalone, Preroide, Mestalone, Methyldihydrotestosterone, 17beta-Hydroxy-17alpha-methyl-5alpha-androstan-3-one, NSC 18219, RU 143, (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one, 17.alpha.-Methyldihydrotestosterone, 17.alpha.-Methyl-5.alpha.-dihydrotestosterone, 17.beta.-Hydroxy-17-methyl-5.alpha.-androstan-3-one, 5.alpha.-Androstan-3-one, 17.beta.-hydroxy-17-methyl-, 5.alpha.-Androstane-17.alpha.-methyl-17.beta.-ol-3-one, 17.alpha.-Methyl-17.beta.-hydroxy-5.alpha.-androstan-3-one, 17alpha-Methyldihydrotestosterone, Mestanolonum [INN-Latin], Mestanolona [INN-Spanish], 17alpha-Methylandrostanolone, Mestanolone (1.0mg/ml in Acetonitrile), SMR000238198, Mestanolone [INN:BAN:JAN], 17-alpha-Methyldihydrotestosterone, EINECS 208-302-6, Stanozolol EP Impurity A, 17-Methyldihydrotestosterone, BRN 3207223, 17.beta.-Hydroxy-17.alpha.-methyl-5.alpha.-androstan-3-one, 17alpha-Methyl-5alpha-dihydrotestosterone, UNII-S712YZ168E, Mesanolon (TN), NCGC00183127-01, 17alpha-methyl-5alpha-androstan-17beta-ol-3-one, 17beta-Hydroxy-17-methyl-5alpha-androstan-3-one, 5alpha-Androstane-17alpha-methyl-17beta-ol-3-one, 17-beta-Hydroxy-17-methyl-5-alpha-androstan-3-one, 17alpha-Methyl-17beta-hydroxy-5alpha-androstan-3-one, 5-alpha-Androstane-17-alpha-methyl-17-beta-ol-3-one, Androstan-3-one, 17-hydroxy-17-methyl-, (5a,17b)-, 17-.alpha.-Methylandrostan-17-.beta.-ol-3-one, Mestanolone (JAN/INN), MESTANOLONE [MI], MESTANOLONE [INN], MESTANOLONE [JAN], Stanozolol impurity A CRS, 17.beta.-Hydroxy-17-methyl-5.alpha.-androstan-3-one #, 5.alpha.-Androstan-3-on-17.beta.-ol, 17.alpha.-methyl, MESTANOLONE [MART.], MESTANOLONE [WHO-DD], 4-08-00-00656 (Beilstein Handbook Reference), MLS000759515, MLS001424090, SCHEMBL146678, 5alpha-Androstan-3-one, 17beta-hydroxy-17-methyl-, Androstan-3-one, 17-hydroxy-17-methyl-, (5.alpha.,17.beta.)-, CHEMBL261514, CHEBI:31825, 5-alpha-ANDROSTAN-3-ONE, 17-beta-HYDROXY-17-METHYL-, Androstan-3-one, 17-hydroxy-17-methyl-, (5alpha,17beta)-, HMS2051M18, Androstan-3-one, 17-hydroxy-17-methyl-, (5-alpha,17-beta)-, HY-B1903, NSC18219, Tox21_113424, BDBM50423547, LMST02020027, MSK8504-100A, AKOS015895448, MSK8504-1000A, CCG-100893, CS-5233, Mestanolone (1 mg/ml in Acetonitrile), Mestanolone 100 microg/mL in Methanol, NC00143, (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13,17-trimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one, AC-16142, CAS-521-11-9, CPD000238198, FM156785, STANOZOLOL IMPURITY A [EP IMPURITY], NS00032423, 17B-hydroxy-17A-methyl-5A-androstan-3-one, D01533, Mestanolone Solution in Acetonitrile, 100ug/mL, Mestanolone Solution in Acetonitrile, 1000ug/mL, Q1924446, (5alpha,17beta)-17-hydroxy-17-methylandrostan-3-one, 17.ALPHA.-METHYLANDROSTAN-17.BETA.-OL-3-ONE, 17.ALPHA.-METHYLANDROSTAN-3-ON-17.BETA.-OL, 17.BETA.-HYDROXY-17.ALPHA.-METHYL-3-ANDROSTANONE, 17alpha-Methylandrostan-17beta-ol-3-one, analytical standard, (5.ALPHA.,17.BETA.)-17-HYDROXY-17-METHYLANDROSTAN-3-ONE, Stanozolol impurity A, European Pharmacopoeia (EP) Reference Standard, (5S,8R,10S,13S,17S)-17-Hydroxy-10,13,17-trimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one, (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13,17-trimethyltetradecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
Theoretical properties:
molecular_formula: C20H32O2
molecular_weight: 304.5 g/mol
exact_mass: 304.240230259 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 22
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Mestanolone is a 3-oxo-5alpha-steroid.
chembl: MESTANOLONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Mestanolone, also known as methylandrostanolone and sold under the brand names Androstalone and Ermalone among others, is an androgen and anabolic steroid (AAS) 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 (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). 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.