(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

• ChemBase ID: 72779
• Molecular Formular: C20H30O2
• Molecular Mass: 302.451
• Monoisotopic Mass: 302.2245802
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)C)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(C)O)C)C
• 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
• InChIKey: GCKMFJBGXUYNAG-HLXURNFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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; (1S,2R,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: dianabol; methyltestosterone
• Synonyms: 17α-Methyl-4-androsten-17β-ol-3-one; 17β-Hydroxy-17α-methyl-4-androsten-3-one; Mesterone; Methyltestosterone; 4-Androsten-17α-methyl-17β-ol-3-one; 17-Hydroxy-17-methyl-3-keto-androstene-4; 17-Methyltestosteron; Androsten; Dumogran; Metrone; NSC 139965; Testora; Testoviron; U 2842; 17α-Methyl Testosterone; Android; Testred; Virilon; 17-Methyltestoster; Methyltestosterone; 17α-Methyltestosterone; (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; Methyl testosteronum; (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; 17α-甲基-4-雄甾烯-17β-醇-3-酮; 17β-羟基-17α-甲基-4-雄甾烯-3-酮; 甲基睾甾酮; 甲睾酮; 17α-甲基睾甾酮

Database IDs

• CAS Number: 58-18-4
• EC Number: 200-366-3
• MDL Number: MFCD00003655
• Beilstein Number: 2057425
• PubChem SID: 24885900; 162037700; 24885901; 24897147; 24870181
• PubChem CID: 6010

CALCULATED PROPERTIES

• Acid pKa: 19.086739
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.6459997
• LogD (pH = 7.4): 3.646
• Log P: 3.646
• Molar Refractivity: 89.068 cm^3
• Polarizability: 35.103523 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble4.8 mg/mL; Dioxane; ethanol: soluble22 mg/mL; H2O: ≤0.5 mg/mL; Methanol
• Apperance: White Solid; white solid (photosensitive)
• Melting Point: 162-168 °C(lit.); 165-168°C
• Optical Rotation: [α]20/D +82±3°, c = 1% in ethanol
• Hydrophobicity(logP): 3.928

Safety Information

• Storage Condition: -20°C; Controlled Substance, -20°C Freezer
• RTECS: BV8400000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-63
• Safety Statements: 53-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H350-H361
• GHS Precautionary statements: P201-P281-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Gloves, type P2 (EN 143) respirator cartridges
• Drug Control: USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule IIIN; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Gene Information: rat ... Ar(24208)

Product Information

• Purity: ≥97.0% (HPLC); 95%
• Grade: USP; VETRANAL™, analytical standard
• Salt Data: Free Base
• Loss on Drying: ≤2% loss on drying
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Empirical Formula (Hill Notation): C20H30O2
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Selleck Chemicals - S1678

Related research area: Endocrinology

Sigma Aldrich - M7252

Biochem/physiol Actions
Methyltestosterone (Mesterone) is an androgen and anabolic steroid.

Sigma Aldrich - 69241

Other Notes
Sales restrictions may apply

Sigma Aldrich - 69240

Other Notes
Sales restrictions may apply

Sigma Aldrich - 46444

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M326400

Androgen. It has been used as an androgenic agent. Controlled substance (anabolic steroid).

REFERENCES

• http://en.wikipedia.org/wiki/Methyltestosterone
• Bichet, N., et al.: Toxicol. Appl. Pharmacol., 106, 509 (1990)
• Gustafson, D., et al.: Toxicol. Sci., 53, 245 (1990)
• Copple, B., et al.: Toxicol. Sci., 77, 172 (1990)
• Takashima, K., et al.: Life Sci., 78, 2787 (1990)