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

• ChemBase ID: 136687
• Molecular Formular: C16H15NO
• Molecular Mass: 237.2964
• Monoisotopic Mass: 237.11536411
• SMILES: c1ccc2c(c1)CCc1ccccc1C2C(=O)N
• Canonical SMILES: NC(=O)C1c2ccccc2CCc2c1cccc2
• InChI: InChI=1S/C16H15NO/c17-16(18)15-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)15/h1-8,15H,9-10H2,(H2,17,18)
• InChIKey: APBVLLORZMAWKI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tricyclo[9.4.0.0^3,^8]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide; tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide
• IUPAC Traditional name: cyheptamide; tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene-2-carboxamide
• Synonyms: 10,11-Dihydro-5H-dibenzo(a,d)cycloheptene-5-carboxamide; Cyheptamide; 10,11-Dihydro-5H-dibenzo[a,d]cycloheptene-5-carboxamide; AY 8682; BS 7029; Carbamazepam; ICI 51426; Cyheptamide; 10,11-二氢-5H-二苯并(a,d)环庚烯-5-羧酰胺; 环庚米特

Database IDs

• CAS Number: 7199-29-3
• EC Number: 230-570-8
• MDL Number: MFCD00467136
• PubChem SID: 24892575; 162230957
• PubChem CID: 23603

CALCULATED PROPERTIES

• Acid pKa: 16.317795
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.0439587
• LogD (pH = 7.4): 3.0439587
• Log P: 3.0439587
• Molar Refractivity: 72.1375 cm^3
• Polarizability: 27.627062 Å^3
• Polar Surface Area: 43.09 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 189-191°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: HO7878000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Empirical Formula (Hill Notation): C16H15NO

DETAILS

Sigma Aldrich - C4080

Packaging
5 mg in glass bottle
Application
Used to study pharmacological activity involved in identification of compounds with central nervous system activity1

Toronto Research Chemicals - C989040

An analogue of Carbamazepine (C175840). The toxicity of Cyheptamide in mice and rats is very low, and anticonvulsant activity is marked. Carbamazepine and Cyheptamide have certain stereochemical features in common with Phenytoin.

REFERENCES

• Platt, D.S., et al.: Biochem. Pharmacol., 18, 429 (1969)
• Kraml, M., et al.: Biochem. Pharmacology, 20, 2327 (1969)