Compound: methyltestosterone
SMILES: O=C1C=C2[C@]([C@@H]3[C@H]([C@H]4[C@]([C@](O)(C)CC4)(C)CC3)CC2)(C)CC1
InChIKey: GCKMFJBGXUYNAG-HLXURNFRSA-N
Synonyms: methyltestosterone, 17-Methyltestosterone, 58-18-4, Metandren, Testred, Android, 17alpha-Methyltestosterone, Androsten, Dumogran, Malestrone, Masenone, Mastestona, Steronyl, Synandrets, Synandrotabs, Hormale, Malogen, Metrone, Testora, Oreton Methyl, Glosso-sterandryl, Neo-Hombreol-M, Oreton-M, Android 5, Methitest, Android 10, Android 25, Orchisterone-M, Metiltestosterona, NSC-9701, Estratest, 17beta-Hydroxy-17-methylandrost-4-en-3-one, Methyltestosteronum, Anertan (tablets), Androsan (tablets), Metiltestosterone, RU 24400, Methyltestosterone ciii, 17alpha-Methyl-3-oxo-4-androsten-17beta-ol, 4-Androstene-17alpha-methyl-17beta-ol-3-one, 17-beta-Hydroxy-17-methylandrost-4-en-3-one, DTXSID1033664, V9EFU16ZIF, L 589.372, NSC-139965, 17alpha-Methyl-delta-androsten-17beta-ol-3-one, CDB-110, Androst-4-en-3-one, 17-hydroxy-17-methyl-, (17beta)-, Androst-4-en-3-one, 17beta-hydroxy-17-methyl-, RU-24400, (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one, DTXCID9013664, CHEBI:27436, NSC9701, U-2842, 17beta-Hydroxy-17alpha-methylandrost-4-en-3-one, L-589372, L-589.372, 17 alpha Methyltestosterone, 17alpha-methyl-Delta4-androsten-17beta-ol-3-one, (17beta)-17-hydroxy-17-methylandrost-4-en-3-one, 17alpha-methyl-Delta(4)-androsten-17beta-ol-3-one, 17(alpha)-methyl-Delta(4)-androsten-17(beta)-ol-3-one, 17beta-Methyltestosterone, 17 beta-Methyltestosterone, 17 Epimethyltestosterone, 17beta Methyltestosterone, 17alpha Methyltestosterone, 17 beta Methyltestosterone, 17alpha Methyl Testosterone, 17alpha-Methyl-Testosterone, Testomet, Testovis, Eldec, Plex hormone, Potensan fte, Neohombreol M, Testotonic B, 17beta-Hydroxy-17-methyl-4-androsten-3-one, Ero Test, 17 beta-Hydroxy-17-methyl-4-androsten-3-one, (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta(a)phenanthren-3-one, RefChem:55623, 17beta Hydroxy 17 methyl 4 androsten 3 one, 17 beta Hydroxy 17 methyl 4 androsten 3 one, G03BA02, G03EK01, 17 Alpha-methyl-delta4-androsten-17beta-ol-4-one, (1S,2R,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyltetracyclo(8.7.0.02,7.011,15)heptadec-6-en-5-one, 200-366-3, Androsan, Mesterone, Virilon, Andrometh, Homandren, Metestone, Nabolin, Oraviron, Syndren, M.T.Mucorettes, Nu-man, Testovis Depot, Homandren, tablets, 17-Methyltestosteron, CDB 110, Anertan, tablets, 17-Hydroxy-17-methyl-3-keto-androstene-4, 17-alpha-Methyltestosterone, 17.alpha.-Methyltestosterone, 17|A-Methyltestosterone, U 2842, Oreton M, Androsan, tablets, component of Estan, Neo-Hombreol [M], Neo-Homobreol (M), Neo-Homobreol [M], component of Gynetone, NCGC00091009-03, Androst-4-en-3-one, 17-hydroxy-17-methyl-, (17.beta.)-, component of Tylosterone, 17a-methyl testosterone, Glosso sterandryl, Testosterone, 17-methyl-, Homandren (VAN), Testovis (tablet), 17.alpha.-Methyl-3-oxo-4-androsten-17.beta.-ol, Androsan (VAN), Testoviron (VAN), Anertan (VAN), 4-Androstene-17.alpha.-methyl-17.beta.-ol-3-one, Androst-4-en-3-one, 17.beta.-hydroxy-17-methyl-, Testoviron (tablet), Oretron, Estan (Salt/Mix), Metiltestosterone [DCIT], CAS-58-18-4, Estratest (Salt/Mix), SMR000058528, Android (TN), CCRIS 3723, Methyltestosteronum [INN-Latin], Metiltestosterona [INN-Spanish], HSDB 3365, 17?-Methyl Testosterone (1.0 mg/mL in Methanol), WLN: L E5 B666 OV MUTJ A E FQ F -B&AEF, EINECS 200-366-3, UNII-V9EFU16ZIF, NSC 139965, BRN 2057425, component of Gynetone (Salt/Mix), Premarin with methyltestosterone, 4-Androstene-17-alpha-methyl-17-beta-ol-3-one, NCGC00091009-04, NCGC00091009-05, (1S,3aS,3bR,9aR,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one, Testred (TN), (17-beta)-17-Hydroxy-17-methylandrost-4-en-3-one, Premarin with Methyltestosterone (Salt/Mix), 17(alpha)-Methyl-delta4-androsten-17(beta)-ol-3-one, 17-Hydroxy-17-methylandrost-4-en-3-one #, Androst-4-en-3-one, 17-hydroxy-17-methyl-, (17b)-, Methyltestosterone CRS, 17a-methyltestosterone, Methyltestosterone [USP:INN:BAN:JAN], 17-.beta.-Hydroxy-17-methylandrost-4-en-3-one, Androst-4-en-3-on-17.beta.-ol, 17.alpha.-methyl, METHYL TESTOSTERONE, Methyltestosterone solution, Androst-4-ene-17.alpha.-methyl-17.beta.-ol-3-one, 17.beta.-Hydroxy-17.alpha.-methylandrost-4-en-3-one, 17.alpha.-methyl-.DELTA.4-androsten-17.beta.-ol-3-one, CHEMBL1395, SCHEMBL18657, 4-08-00-01010 (Beilstein Handbook Reference), Androst-4-en-3-one, 17-beta-hydroxy-17-methyl-, MLS000759474, MLS001424040, MLS002174282, GTPL6945, METHYLTESTOSTERONE [INN], METHYLTESTOSTERONE [JAN], METHYLTESTOSTERONE [HSDB], .ALPHA.-METHYLTESTOSTERONE, METHYLTESTOSTERONE [VANDF], 17-MT, HMS2051A14, HMS2272A06, METHYLTESTOSTERONE [MART.], METHYLTESTOSTERONE [USP-RS], METHYLTESTOSTERONE [WHO-DD], METHYLTESTOSTERONE [WHO-IP], (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one, 17-METHYLTESTOSTERONE [MI], HY-A0121, Tox21_113161, Tox21_113162, Tox21_400058, BDBM50410531, LMST02020029, Methyltestosterone (JP17/USP/INN), MSK2221-100A, NSC139965, AKOS015917317, MSK2221-1000A, Tox21_113162_1, CCG-100871, CS-5099, DB06710, GS-6594, NC00121, METHYLTESTOSTERONE [ORANGE BOOK], METHYLTESTOSTERONE [EP MONOGRAPH], NCGC00091009-01, NCGC00091009-06, NCGC00091009-07, Oxandrolone impurity, methyltestosterone-, (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, FM112033, METHYLTESTOSTERONE [USP MONOGRAPH], METHYLTESTOSTERONUM [WHO-IP LATIN], SMR001261452, M0435, Methyltestosterone for system suitability CRS, NS00010270, 17alpha-Methyltestosterone, >=97.0% (HPLC), 17Alpha-Methyltestosterone, 1mg/ml in Methanol, C07198, D00408, Methyltestosterone (17alpha-Methyltestosterone), AB00443683-06, AB00443683-09, 17alpha-Methyltestosterone, solid (photosensitive), Q421768, BRD-K84036904-001-08-8, Methyltestosterone Solution in Acetonitrile, 100ug/mL, Methyltestosterone Solution in Acetonitrile, 1000ug/mL, 17-alpha-Methyltestosterone 100 microg/mL in Acetonitrile, 17alpha-Methyltestosterone, VETRANAL(TM), analytical standard, OXANDROLONE IMPURITY, METHYLTESTOSTERONE- [USP IMPURITY], Methyltestosterone, European Pharmacopoeia (EP) Reference Standard, Methyltestosterone (17alpha-Methyltestosterone) 1.0 mg/ml in Acetonitrile, Methyltestosterone, United States Pharmacopeia (USP) Reference Standard, Methyltestosterone for system suitability, European Pharmacopoeia (EP) Reference Standard, (1S,2R,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one, (8R,10R,13S,17S)-17-Hydroxy-10,13,17-trimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
Theoretical properties:
molecular_formula: C20H30O2
molecular_weight: 302.5 g/mol
exact_mass: 302.224580195 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:
physical_state: Crystals from hexane
color: Crystals from hexane
odor: Odorless
flash_point: 41 °F
Descriptions:
pubchem: Methyltestosterone can cause developmental toxicity according to state or federal government labeling requirements.
chebi: A 17β-hydroxy steroid that is testosterone bearing a methyl group at the 17α position.
chembl: METHYLTESTOSTERONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is 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. It is taken by mouth or held in the cheek or under the tongue.
Side effects of methyltestosterone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause estrogenic effects like fluid retention, breast tenderness, and breast enlargement in men and 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 moderate androgenic effects and moderate anabolic effects, which make it useful for producing masculinization.
Methyltestosterone was discovered in 1935 and was introduced for medical use in 1936. It was made shortly after the discovery of testosterone and was one of the first synthetic AAS to be developed. In addition to its medical use, methyltestosterone is used to improve physique and performance, although it is not as commonly used as other AAS for such purposes due to its androgenic effects, estrogenic effects, and risk of liver damage. The drug is a controlled substance in many countries and so non-medical use is generally illicit.