1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide

• ChemBase ID: 125776
• Molecular Formular: C22H21Cl2IN4O
• Molecular Mass: 555.23881
• Monoisotopic Mass: 554.01371467
• SMILES: O=C(NN1CCCCC1)c1nn(c2ccc(Cl)cc2Cl)c(c2ccc(I)cc2)c1C
• Canonical SMILES: Ic1ccc(cc1)c1c(C)c(nn1c1ccc(cc1Cl)Cl)C(=O)NN1CCCCC1
• InChI: InChI=1S/C22H21Cl2IN4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-7-16(23)13-18(19)24)21(14)15-5-8-17(25)9-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
• InChIKey: BUZAJRPLUGXRAB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide
• IUPAC Traditional name: 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(piperidin-1-yl)pyrazole-3-carboxamide
• Synonyms: AM 251; 1-(2,4-Dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide; AM251; AM251

Database IDs

• CAS Number: 183232-66-8
• MDL Number: MFCD01861181
• PubChem SID: 24891069; 162220123
• PubChem CID: 2125
• CHEMBL: 285932
• Chemspider ID: 2040
• IUPHAR ligand ID: 744
• Wikipedia Title: AM251

CALCULATED PROPERTIES

• Acid pKa: 12.421545
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 6.2328315
• LogD (pH = 7.4): 6.2328925
• Log P: 6.2328973
• Molar Refractivity: 131.3885 cm^3
• Polarizability: 51.616596 Å^3
• Polar Surface Area: 50.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• 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

Pharmacology Properties

• Target: Cannabinoid Receptor
• Gene Information: mouse ... Cnr1(12801), Cnr2(12802)rat ... Cnr1(25248)

Product Information

• Purity: >98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C22H21N4OCl2I

DETAILS

Sigma Aldrich - A6226

Biochem/physiol Actions
AM251 is a CB1 cannabinoid receptor antagonist.
Other Notes
Salt content may vary.
Application
AM251, a CB1 cannabinoid receptor antagonist, has been used in a study to determine its interaction with hippocampal neurons to enhance spatial memory in mice.

Toronto Research Chemicals - A575805

Inhibitor of CB1 receptors. AM 251is a biarylpyrazole compound which has been considered for many years as the prototypical cannabinoid (CB) receptor antagonist

REFERENCES

• Kesser, C., et al.: Mol. Cell. Endocrinol., 302, 108 (2009)
• Araujo, J., et al.: Pharmacol., 83, 170 (2009)
• Malysz, J., et al.: Eur. J. Pharmacol., 603, 12 (2009)