(1S,2R,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 128545
• Molecular Formular: C18H26O2
• Molecular Mass: 274.39784
• Monoisotopic Mass: 274.19328007
• SMILES: O=C1C=C2[C@@H]([C@H]3CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]3CC2)C)CC1
• Canonical SMILES: O=C1CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
• InChI: InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1
• InChIKey: NPAGDVCDWIYMMC-IZPLOLCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: nandrolone
• Synonyms: 17β-Hydroxy-19-norandrost-4-en-3-one; 17β-Hydroxy-4-estren-3-one; 19-Norandrostenolone; 4-Estren-17β-ol-3-one; Nandrolone; 19-Nortestosterone; Nandrolone; (17β)-17-Hydroxyestr-4-en-3-one; (+)-19-Nortestosterone; 17β-Nandrolone; 17β-Nortestosterone; 17β-Hydroxy-19-nor-4-androsten-3-one; Norandrostenolon; Norandrostenolone; Menidrabol; NSC 3351; Nandrolon; Nortestonate; Oestrenolon; Nandrolone; Nadrolone; 19-Nortestosterone; 19-去甲睾酮; 诺龙; 17β-羟基-19-去甲雄甾-4-烯-3-酮; 17β-羟基-4-雌烯-3-酮; 19-去甲雄甾烯醇酮; 4-雌烯-17β-醇-3-酮; 诺龙; 19-去甲睾酮

Database IDs

• CAS Number: 434-22-0
• EC Number: 207-101-0
• MDL Number: MFCD00003664
• Beilstein Number: 2055849
• PubChem SID: 24886700; 162222852; 24897817; 24870216
• PubChem CID: 9904
• CHEBI ID: 7466
• ATC CODE: A14AB01
• CHEMBL: 757
• Chemspider ID: 9520
• DrugBank ID: DB00984
• Unique Ingredient Identifier: 6PG9VR430D
• Wikipedia Title: Nandrolone

CALCULATED PROPERTIES

• Acid pKa: 19.27889
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.065376
• LogD (pH = 7.4): 3.0653763
• Log P: 3.0653763
• Molar Refractivity: 79.9547 cm^3
• Polarizability: 31.416986 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 112-124°C
• Optical Rotation: [α]20/D +57±2°, c = 1% in chloroform

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• RTECS: KG7964000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 22-24/25-36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• 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

• Admin Routes: Intramuscular
• Bioavailability: 2.24% (Oral); 100% (Intramuscular)
• Excretion: approximate 21 days
• Half Life: 6 days
• Metabolism: Hepatic
• Legal Status: Schedule III (US) ; POM (UK)
• Pregnancy Category: X (US); X (AUS)
• Gene Information: human ... SERPINA6(866), SHBG(6462)rat ... Ar(24208), Nr3c2(25672), Pgr(25154)

Product Information

• Purity: ≥99.0% (HPLC); 97%
• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C18H26O2

DETAILS

Sigma Aldrich - 74640

Other Notes
Sales restrictions may apply

Sigma Aldrich - 46476

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

Toronto Research Chemicals - N315000

An anabolic steroid.Controlled substance (anabolic steroid).

REFERENCES

• Gradeen, C., et al.: J. Anal. Toxicol., 14, 120 (1990)
• Teale, P., et al.: Biol. Mass Spectrom., 20, 109 (1990)
• Yamada, M., et al.: J. Pharm. Biomed. Anal., 45, 125 (1990)
• Yamada, M., et al.: J. Anal. Toxicol., 32, 387 (1990)