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Home> Encyclopedia > Hot Product Listed 1   > 17-Methyltestosterone
58-18-4 structure

17-Methyltestosterone

Iupac Name:(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
CAS No.:58-18-4
EINECS(EC#): 200-366-3
Molecular Weight:302.45
Molecular Formula:C20H30O2 (isomer)
Names and Identifiers
Synonyms

(17-beta)-17-Hydroxy-17-methylandrost-4-en-3-one (17beta)-17-hydroxy-17-methylandrost-4-en-3-one (1S,2R,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0(2),.0(1)(1),(1)]heptadec-6-en-5-one (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,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 (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 17 beta-Hydroxy-17-methyl-4-androsten-3-one 17 beta-Methyltestosterone 17(alpha)-methyl-Delta(4)-androsten-17(beta)-ol-3-one 17(alpha)-Methyl-delta4-androsten-17(beta)-ol-3-one 17.alpha.-methyl-.DELTA.4-androsten-17.beta.-ol-3-one 17.alpha.-Methyl-3-oxo-4-androsten-17.beta.-ol 17.alpha.-Methyltestosterone 17.beta.-Hydroxy-17.alpha.-methylandrost-4-en-3-one 17-.beta.-Hydroxy-17-methylandrost-4-en-3-one 17|A-Methyltestosterone 17alpha-Methyl-3-oxo-4-androsten-17beta-ol 17ALPHA-METHYL-4-ANDROSTEN-17BETA-OL-3-ONE 17alpha-methyl-Delta(4)-androsten-17beta-ol-3-one 17alpha-methyl-Delta4-androsten-17beta-ol-3-one 17alpha-Methyl-delta-androsten-17beta-ol-3-one 17-alpha-Methyltestosterone 17ALPHA-METHYLTESTOSTERONE 17-alpha-Methyltestosterone 100 microg/mL in Acetonitrile 17alpha-Methyltestosterone solution, 1.0 mg/mL in 1,2-dimethoxyethane, ampule of 1 mL, certified reference material 17alpha-Methyltestosterone, >=97.0% (HPLC) 17alpha-Methyltestosterone, solid (photosensitive) 17alpha-Methyltestosterone, VETRANAL(TM), analytical standard 17BETA-HYDROXY-17ALPHA-METHYL-4-ANDROSTEN-3-ONE 17beta-Hydroxy-17-methyl-4-androsten-3-one 17-beta-Hydroxy-17-methylandrost-4-en-3-one 17beta-Hydroxy-17-methylandrost-4-en-3-one 17beta-Methyltestosterone 17-Epimethyltestosterone 17-Hydroxy-17-methyl-3-keto-androstene-4 17-Hydroxy-17-methylandrost-4-en-3-one # 17-Methyltestoster 17-Methyltestosteron 17-MT 262423-02-9 4-08-00-01010 (Beilstein Handbook Reference) 4-ANDROSTEN-17ALPHA-METHYL-17BETA-OL-3-ONE 4-Androstene-17.alpha.-methyl-17.beta.-ol-3-one 4-Androstene-17-alpha-methyl-17-beta-ol-3-one 4-Androstene-17alpha-methyl-17beta-ol-3-one 58-18-4 AB00443683-06 AB00443683-09 AC1L1LLR ACN-031982 AKOS015917317 AN-41744 Android Android (TN) Android 10 Android 25 Android 5 Android-10 Android-25 Android-5 Andrometh Androsan Androsan (tablets) Androsan (VAN) Androsan, tablets Androst-4-en-3-on-17.beta.-ol, 17.alpha.-methyl Androst-4-en-3-one, 17.beta.-hydroxy-17-methyl- Androst-4-en-3-one, 17-beta-hydroxy-17-methyl- Androst-4-en-3-one, 17beta-hydroxy-17-methyl- Androst-4-en-3-one, 17-hydroxy-17-methyl-, (17b)- Androst-4-en-3-one, 17-hydroxy-17-methyl-, (17beta)- Androst-4-ene-17.alpha.-methyl-17.beta.-ol-3-one Androsten Anertan Anertan (tablets) Anertan (VAN) Anertan, tablets API0003346 BDBM50410531 BRN 2057425 C07198 CAS-58-18-4 CCG-100871 CCRIS 3723 CDB 110 CHEBI:27436 CHEMBL1395 CJ-10774 component of Estan component of Gynetone component of Gynetone (Salt/Mix) component of Tylosterone Conjugated estrogens / methyltestosterone Conjugated estrogens mixture with methyltestosterone CS-5099 D00408 DB06710 DSSTox_CID_13664 DSSTox_GSID_33664 DSSTox_RID_79089 DTXSID1033664 Dumogran EINECS 200-366-3 Estan (Salt/Mix) Estratest Estratest (Salt/Mix) Estratest H.S. Estratest HS Estratest-HS GCKMFJBGXUYNAG-HLXURNFRSA-N Glosso sterandryl Glosso-sterandryl GS-6594 GTPL6945 HMS2051A14 HMS2272A06 Homandren Homandren (VAN) Homandren, tablets Hormale HSDB 3365 HY-A0121 I14-9703 L 589.372 LMST02020029 LS-19506 M.T.Mucorettes M0435 Malestrone Malogen Masenone Mastestona MCULE-5274452426 Mesteron MESTERONE METANDREN Metestone Methitest METHYL TESTOSTERONE METHYLTESTOSTERONE Methyltestosterone (17alpha-Methyltestosterone) Methyltestosterone (17alpha-Methyltestosterone) 1.0 mg/ml in Acetonitrile Methyltestosterone (JP17/USP/INN) Methyltestosterone [USAN:INN:BAN:JAN] Methyltestosterone [USP:INN:BAN:JAN] Methyltestosterone for system suitability, European Pharmacopoeia (EP) Reference Standard Methyltestosterone mixture with conjugated estrogens Methyltestosterone, European Pharmacopoeia (EP) Reference Standard Methyltestosterone, United States Pharmacopeia (USP) Reference Standard Methyltestosteronum Methyltestosteronum [INN-Latin] Metiltestosterona Metiltestosterona [INN-Spanish] Metiltestosterone Metiltestosterone [DCIT] Metrone MLS000759474 MLS001424040 MLS002174282 Nabolin NC00121 NCGC00091009-01 NCGC00091009-03 NCGC00091009-04 NCGC00091009-05 NCGC00091009-06 NCGC00091009-07 Neo-Hombreol [M] Neo-Hombreol-M Neo-Homobreol (M) Neo-Homobreol [M] NSC 139965 NSC139965 NSC-139965 NSC9701 NSC-9701 Nu-man Oraviron Orchisterone-M Oreton M Oreton Methyl Oreton-M Oretron Premarin with methyltestosterone Premarin with Methyltestosterone (Salt/Mix) RU 24400 SC-16208 SCHEMBL18657 SMR000058528 SMR001261452 Steronyl Synandrets Synandrotabs Syndren Testhormone Testora Testosterone, 17-methyl- Testoviron (tablet) Testoviron (VAN) Testovis (tablet) Testovis Depot Testred Testred (TN) TL8003728 Tox21_113161 Tox21_113162 Tox21_113162_1 Tox21_400058 U 2842 UNII-V9EFU16ZIF V9EFU16ZIF Virilon WLN: L E5 B666 OV MUTJ A E FQ F -B&AEF ZINC3814422

Inchi
InChI=1S/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
InChkey
GCKMFJBGXUYNAG-HLXURNFRSA-N
Canonical Smiles
CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4(C)O)C
Isomers Smiles
C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C)O)C
Properties
Appearance
White to Off-White Crystalline Powder
Density
1.0434 (rough estimate)
Melting Point
162-168 °C(lit.)
Boiling Point
383.47°C (rough estimate)
Vapour
1.8X10-8 mm Hg at 25 deg C (est)
Refractive Index
1.4800 (estimate)
Flash Point
5 °C
Alpha
79 ° (C=1, ALCOHOL)
Solubility
Practically Insoluble
Color/Form
white
Other physical and chemical properties
Solid
Stability
Stable under normal temperatures and pressures.
Storage temp
2-8°C
Spectral properties
Specific optical rotation: +69 to +75 deg at 25 deg C/D (dioxane)
MAX ABSORPTION (97% SULFUR): 298 NM (LOG E= 4.26); 497 NM (LOG E= 2.86)
IR: 5051 (Coblentz Society Spectral Collection)
UV: 4-837 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
MASS: 64978 (NIST/EPA/MSDC Mass Spectral Data Base, 1990 Version)
Safety and Handling
Hazard Codes
T,Xn,F,Xi
Risk Statements
45-63-22-20-19-11-61-60-36/37/38-38-10
Safety Statements
53-36/37-45-24/25-22
HazardClass
6.1(b)
Safety
Hazard Codes:T,Xn,Xi ,F
Risk Statements: 45-63-22-20-19-11-61-60-36/37/38
R45:May cause cancer.
R63:Possible risk of harm to the unborn child.
R22:Harmful if swallowed.
R20:Harmful by inhalation.
R19:May form explosive peroxides.
R11:Highly flammable.
R60:May impair fertility.
R61:May cause harm to the unborn child.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 53-36/37-45-24/25-22
S53:Avoid exposure - obtain special instructions before use.
S36/37:Wear suitable protective clothing and gloves.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S24/25:Avoid contact with skin and eyes.
S22:Do not breathe dust.
RIDADR: 3249
WGK Germany: 3
RTECS: BV8400000
HazardClass: 6.1(b)
PackingGroup: III
Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 39mg/kg/33W-I (39mg/kg) LIVER: "JAUNDICE, CHOLESTATIC" American Journal of Gastroenterology. Vol. 82, Pg. 461, 1987.
mouse LD50 intraperitoneal 400mg/kg (400mg/kg) Drugs in Japan Vol. 6, Pg. 830, 1982.
mouse LD50 oral 1860mg/kg (1860mg/kg) Drugs in Japan Vol. 6, Pg. 830, 1982.
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg) Drugs in Japan Vol. 6, Pg. 830, 1982.
rat LD50 intraperitoneal 1050mg/kg (1050mg/kg) Drugs in Japan Vol. 6, Pg. 830, 1982.
rat LD50 oral 2500mg/kg (2500mg/kg) Drugs in Japan Vol. 6, Pg. 830, 1982.
rat LD50 subcutaneous 5gm/kg (5000mg/kg) Drugs in Japan Vol. 6, Pg. 830, 1982.

PackingGroup
III
Transport
3249
Formulations/Preparations
Oral: Capsules: 10 mg Android (C-III), (Valeant); Testred (C-III), (Valeant); Virilon (C-III), (Star). Oral: Tablets: 10 mg Methitest, (Global), 25 mg Methitest, (Global).
Grade: NF
USP, BP, micronized grades
Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl methyltestosterone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule III shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation containing any quantity of the following substances, including its salts, isomers, and salts of isomers whenever the existence of such salts of isomers is possible within the specific chemical designation. DEA Code #: 4000; Drug class: anabolic steroids.
Specification
Methyltestosterone (CAS NO. 58-18-4), its Synonyms are (17-beta)-17-Hydroxy-17-methylandrost-4-en-3-one ; 17(alpha)-Methyl-delta4-androsten-17(beta)-ol-3-one ; 17-Hydroxy-17-methyl-3-keto-androstene-4 ; 17-beta-Hydroxy-17-methylandrost-4-en-3-one ; 17alpha-Methyl-3-oxo-4-androsten-17beta-ol ; 17alpha-Methyl-delta-androsten-17beta-ol-3-one ; M.T.Mucorettes ; Malestrone ; Androst-4-en-3-one, 17-beta-hydroxy-17-methyl- ; Androst-4-en-3-one, 17-hydroxy-17-methyl-, (17beta)- ; Androst-4-en-3-one, 17beta-hydroxy-17-methyl- .
Octanol/Water Partition Coefficient
log Kow = 3.36
Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Carcinogenicity, Category 1B

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H350 May cause cancer

H361 Suspected of damaging fertility or the unborn child

Precautionary statement(s)
Prevention

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

Precursor and Product
Computational chemical data
  • Molecular Weight:302.45g/mol
  • Molecular Formula:C20H30O2
  • Compound Is Canonicalized:True
  • XLogP3-AA:3.4
  • Exact Mass:302.225
  • Monoisotopic Mass:302.225
  • Complexity:550
  • Rotatable Bond Count:0
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:2
  • Topological Polar Surface Area:37.3A^2
  • Heavy Atom Count:22
  • Defined Atom Stereocenter Count:6
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
  • CACTVS Substructure Key Fingerprint: AAADceB4MAAAAAAAAAAAAAAAAAAAAYAAAAAwYIAAAAAAAGDAAAAAGgAACAAAD0SAgAACAAAAAgCI AqBSAAAAAAAgAAAACAEAAEgAABIAAQAAQAAEgAAIAQOIyPCPgAAAAAAAAACAAAQAACAAAYAADAAA AA==
 
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