2-[6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylacetamide

• ChemBase ID: 154963
• Molecular Formular: C21H23Cl2N3O
• Molecular Mass: 404.33282
• Monoisotopic Mass: 403.12181773
• SMILES: CCCN(CCC)C(=O)Cc1c(nc2n1cc(cc2)Cl)c1ccc(cc1)Cl
• Canonical SMILES: CCCN(C(=O)Cc1c(nc2n1cc(Cl)cc2)c1ccc(cc1)Cl)CCC
• InChI: InChI=1S/C21H23Cl2N3O/c1-3-11-25(12-4-2)20(27)13-18-21(15-5-7-16(22)8-6-15)24-19-10-9-17(23)14-26(18)19/h5-10,14H,3-4,11-13H2,1-2H3
• InChIKey: JRTIDHTUMYMPRU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylacetamide
• IUPAC Traditional name: alpidem
• Synonyms: 6-Chloro-2-(4-chlorophenyl)-N,N-dipropyl-imidazo[1,2-a]pyridine-3-acetamide; 6-Chloro-2-(p-chlorophenyl)-N,N-dipropylimidazo(1,2-a)pyridine-3-acetamide; Ananxyl; SL 80.0342-00; Alpidem; Alpidem

Database IDs

• CAS Number: 82626-01-5
• MDL Number: MFCD00866978
• PubChem SID: 162249101
• PubChem CID: 54897

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.7436113
• LogD (pH = 7.4): 4.954002
• Log P: 4.9575343
• Molar Refractivity: 111.6561 cm^3
• Polarizability: 43.907253 Å^3
• Polar Surface Area: 37.61 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO: ≥10 mg/mL; Methanol
• Apperance: White to Off-White Solid; white to tan powder
• Melting Point: 136-138°C

Safety Information

• Storage Condition: Refrigerator
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H23Cl2N3O

DETAILS

Sigma Aldrich - A1862

Biochem/physiol Actions
Alpidem is a potent antagonist of peripheral benzodiazepine receptor (PBR) that is located on the outer mitochondrial membrane and interacts with the mitochondrial permeability transition (MPT) pore. Alpidem is an anxiolytic drug from the imidazopyridine family. Alpidem acts selectively on the α3 receptor subtype and to a lesser extent at the α1 subtype (Kd of 0.33nM and 1.67nM respectively), of the benzodiazepine receptor.

Toronto Research Chemicals - A575560

A peripheral benzodiazepine GABAA receptor ligand, a new anxiolytic.

REFERENCES

• Rietjens, I., et al.: C
• Min, D., et al.: Pharmacotherapy, 12, 68 (1992)
• Rothwell, C., et al.: J. Toxicol. Sci., 27, 35 (1992)
• Gonzalez-Diaz, H., et al.: Bioorg. Med. Chem. Lett., 15, 1651 (1992)
• Boelsterli, U., et al.: Curr. Drug Metab., 7, 715 (1992)