Compound: Normethandrone
SMILES: O=C1C=C2[C@@H]([C@@H]3[C@H]([C@H]4[C@]([C@](O)(C)CC4)(C)CC3)CC2)CC1
InChIKey: ZXSWTMLNIIZPET-ZOFHRBRSSA-N
Synonyms: Normethandrone, Methylestrenolone, Matronal, Lutenin, 514-61-4, Normetandrone, Orgasteron, Methylnortestosterone, Methyloestrenolone, 17-Methyl-19-nortestosterone, 17alpha-Methyl-19-nortestosterone, NSC-10039, 743F1Z557A, 17-beta-Hydroxy-17-methylestr-4-en-3-one, DTXSID4023383, 17-alpha-Methyl-17-beta-hydroxy-4-estren-3-one, 17-alpha-methyl-19-nortestosterone, ESTR-4-EN-3-ONE, 17-beta-HYDROXY-17-alpha-METHYL-, NSC10039, RefChem:166651, DTXCID503383, (1S,2R,10R,11S,14S,15S)-14-hydroxy-14,15-dimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadec-6-en-5-one, 208-183-0, Normethandrolone, Metalutin, Methalutin, Normethisterone, NSC 10039, Normethanedrolone, 19-Nortestosterone, 17-methyl-, (8R,9S,10R,13S,14S,17S)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one, 17.alpha.-Methyl-19-nortestosterone, 17beta-hydroxy-17alpha-methylestr-4-en-3-one, 17.alpha.-Methyl-17.beta.-hydroxyestr-4-en-3-one, Orosteron, Orga-Steron, 19-Normethisterone, Normethandrone (1.0mg/ml in Acetonitrile), 17.alpha.-Methylestrenolone, 17alpha-Methylestrenolone, UNII-743F1Z557A, 17-beta-Hydroxy-17-alpha-methyloestr-4-en-3-one, 19-Nor-17-alpha-methyltestosterone, EINECS 208-183-0, BRN 2622263, 17beta-Hydroxy-17-methyl-4-estren-3-on, Estr-4-en-3-one, 17.beta.-hydroxy-17-methyl-, AI3-52808, NORMETHANDRONE [MI], 17.alpha.-Methyl-17.beta.-hydroxy-19-nor-4-androsten-3-one, SCHEMBL148631, NORMETHANDRONE [MART.], NORMETHANDRONE [WHO-DD], CHEMBL2106801, CHEBI:34896, 17alpha-Methyl-17beta-hydroxy-19-nor-4-androsten-3-one, 19-Nor-17-.alpha.-methyltestosterone, DB13533, FM66032, MSK011089-100A, Normethandrone (1 mg/ml in Acetonitrile), 4-Estren-17alpha-methyl-17beta-ol-3-one, NS00032283, (17b)-Hydroxy-17-a-methyloestr-4-en-3-one, 17-.beta.-Hydroxy-17-methylestr-4-en-3-one, 17alpha-Methyl-17beta-hydroxyestr-4-en-3-one, Estr-4-en-3-one, 17beta-hydroxy-17-methyl-, (17beta)-17-hydroxy-17-methylestr-4-en-3-one, Q6824007, 17-.alpha.-Methyl-17-.beta.-hydroxy-4-estren-3-one, 17.alpha.-Hydroxy-17.beta.-methylestr-4-en-3-one #, Estr-4-en-3-one, 17-hydroxy-17-methyl-, (17beta)-, Methylnortestosterone Solution in Acetonitrile, 100ug/mL, 17.alpha.-Methyl-19-norandrost-4-en-17.beta.-ol-3-one, Estr-4-en-3-one, 17-.beta.-hydroxy-17-.alpha.-methyl-, Estr-4-en-3-one, 17-hydroxy-17-methyl-, (17.beta.)-
Theoretical properties:
molecular_formula: C19H28O2
molecular_weight: 288.4 g/mol
exact_mass: 288.208930132 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 21
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Normethandrolone is a steroid. It has a role as an estrogen.
chembl: NORMETHANDRONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase -1.0.
wikipedia: Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. It is taken by mouth.
Side effects of normethandrone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause liver damage. Normethandrone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It is also a synthetic AAS and hence is an agonist of the androgen receptor, the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has some estrogenic activity as well and no other important hormonal activity.
Normethandrone was introduced for medical use by 1957. It is available only in a few countries, including Brazil, Indonesia, and Venezuela, and is available only in combination with methylestradiol or estradiol valerate.