3-{[bis(2H3)methylcarbamoyl]methyl}-2-(4-methylphenyl)imidazo[1,2-a]pyridine-6-carboxylic acid

• ChemBase ID: 179663
• Molecular Formular: C19H19N3O3
• Molecular Mass: 337.37246
• Monoisotopic Mass: 337.14264148
• SMILES: c1cc(cn2c1nc(c2CC(=O)N(C)C)c1ccc(cc1)C)C(=O)O
• Canonical SMILES: Cc1ccc(cc1)c1nc2n(c1CC(=O)N(C)C)cc(cc2)C(=O)O
• InChI: InChI=1S/C19H19N3O3/c1-12-4-6-13(7-5-12)18-15(10-17(23)21(2)3)22-11-14(19(24)25)8-9-16(22)20-18/h4-9,11H,10H2,1-3H3,(H,24,25)
• InChIKey: RFUGIBAONXDHRM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[bis(^2H₃)methylcarbamoyl]methyl}-2-(4-methylphenyl)imidazo[1,2-a]pyridine-6-carboxylic acid
• IUPAC Traditional name: 3-{[bis(^2H₃)methylcarbamoyl]methyl}-2-(4-methylphenyl)imidazo[1,2-a]pyridine-6-carboxylic acid
• Synonyms: 3-[2-(Dimethylamino-d6)-2-oxoethyl]-2-(4-methylphenyl)imidazo[1,2-a]pyridine-6-carboxylic Acid; SL 84.0853-d6; Zolpidem-d6 6-Carboxylic Acid

Database IDs

• CAS Number: 1190014-62-0
• PubChem SID: 164235573
• PubChem CID: 46783280

CALCULATED PROPERTIES

• Acid pKa: 3.4541235
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.27555797
• LogD (pH = 7.4): -1.1447269
• Log P: 0.8726886
• Molar Refractivity: 95.7987 cm^3
• Polarizability: 36.895504 Å^3
• Polar Surface Area: 74.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 158-161°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - Z650012

A major labelled metabolite of Zolpidem.

REFERENCES

• Crestani, F., et al.: Br. J. Pharmacol., 131, 1251 (2000)
• Li, Q., et al.: Bioorg. Med. Chem. Lett., 12, 465 (2000)
• Goulle, J., et al.: Ther. Drug Monit., 26, 206 (2000)
• Ohkanda, J., et al.: J. Med. Chem., 47, 432 (2000)
• Blackaby, W., et al.: Bioorg. M