ethyl N-(2-amino-4-{[(4-fluorophenyl)methyl]amino}phenyl)carbamate

• ChemBase ID: 177433
• Molecular Formular: C16H18FN3O2
• Molecular Mass: 303.3314232
• Monoisotopic Mass: 303.13830505
• SMILES: c1(ccc(cc1)CNc1ccc(c(c1)N)NC(=O)OCC)F
• Canonical SMILES: CCOC(=O)Nc1ccc(cc1N)NCc1ccc(cc1)F
• InChI: InChI=1S/C16H18FN3O2/c1-2-22-16(21)20-15-8-7-13(9-14(15)18)19-10-11-3-5-12(17)6-4-11/h3-9,19H,2,10,18H2,1H3,(H,20,21)
• InChIKey: PCOBBVZJEWWZFR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl N-(2-amino-4-{[(4-fluorophenyl)methyl]amino}phenyl)carbamate
• IUPAC Traditional name: retigabine
• Synonyms: N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamic Acid Ethyl Ester; Ethyl [2-amino-4-[[(4-fluorophenyl)methyl]amino]phenyl]carbamate; D23129; RetigabineSee also: R189051 (HCl salt)

Database IDs

• CAS Number: 150812-12-7
• PubChem SID: 164233343
• PubChem CID: 121892

CALCULATED PROPERTIES

• Acid pKa: 13.604796
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.6849136
• LogD (pH = 7.4): 2.6979141
• Log P: 2.6980824
• Molar Refractivity: 87.0164 cm^3
• Polarizability: 31.129387 Å^3
• Polar Surface Area: 76.38 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Purple Solid
• Melting Point: 138-140°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R189050

A new experimental anticonvulsant drug. Anxiolytic.

REFERENCES

• Dailey, J.W.; et al.: Neuroscience Lett., 195, 77 (1995)
• Korsgaard, M.P.G., et al.: J. Pharmacol. Exp. Ther., 314, 1, 282 (1995)