2-azatricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide

• ChemBase ID: 148042
• Molecular Formular: C15H14N2O
• Molecular Mass: 238.28446
• Monoisotopic Mass: 238.11061308
• SMILES: c1ccc2c(c1)CCc1ccccc1N2C(=O)N
• Canonical SMILES: NC(=O)N1c2ccccc2CCc2c1cccc2
• InChI: InChI=1S/C15H14N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-8H,9-10H2,(H2,16,18)
• InChIKey: PHNLCHMJDSSPDQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide; 2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide
• IUPAC Traditional name: 10,11-dihydrocarbamazepine; 2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide
• Synonyms: 10,11-Dihydro-5H-dibenz[b,f]azepine-5-carboxamide; 10,11-Dihydrocarbamazepine; 10,11-Dihydro Carbamazepine; GP 26-301; Dihydrocarbamazepine; 10,11-二氢-5H-二苯并[b,f]氮杂卓-5-甲酰胺; 10,11-二氢酰胺咪嗪

Database IDs

• CAS Number: 3564-73-6
• EC Number: 222-649-0
• MDL Number: MFCD00005072
• Beilstein Number: 196969
• PubChem SID: 24851693; 162242221
• PubChem CID: 19099

CALCULATED PROPERTIES

• Acid pKa: 15.960306
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.962552
• LogD (pH = 7.4): 2.962552
• Log P: 2.962552
• Molar Refractivity: 70.7714 cm^3
• Polarizability: 26.880587 Å^3
• Polar Surface Area: 46.33 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol
• Apperance: White Solid
• Melting Point: 195-200°C; 204-206°C; 205-210 °C(lit.)

Safety Information

• Storage Condition: Refrigerator
• RTECS: HN8300000
• German water hazard class: 3
• TSCA Listed: 否

Pharmacology Properties

• Mechanism of Action: Adenosine-Agonist-A1; Gabaminergic-A; Sodium channel inhibitor; Sympathomimetic-Alpha-2

Product Information

• Purity: 99%
• Application(s): Anticonvulsant
• Empirical Formula (Hill Notation): C15H14N2O

DETAILS

Sigma Aldrich - 195421

Packaging
100 mg in glass bottle

Toronto Research Chemicals - D448765

A dihydro impurity of Carbamazepine (C175840) from bulk drug.

REFERENCES

• Bhoir, I., et al.: Indian Drugs, 36, 231 (1999)