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

• ChemBase ID: 153856
• Molecular Formular: C23H24Cl2N4O2
• Molecular Mass: 459.36826
• Monoisotopic Mass: 458.12763139
• SMILES: Cc1c(n(nc1C(=O)NN1CCCCC1)c1ccc(cc1Cl)Cl)c1ccc(cc1)OC
• Canonical SMILES: COc1ccc(cc1)c1c(C)c(nn1c1ccc(cc1Cl)Cl)C(=O)NN1CCCCC1
• InChI: InChI=1S/C23H24Cl2N4O2/c1-15-21(23(30)27-28-12-4-3-5-13-28)26-29(20-11-8-17(24)14-19(20)25)22(15)16-6-9-18(31-2)10-7-16/h6-11,14H,3-5,12-13H2,1-2H3,(H,27,30)
• InChIKey: KWDBQJRWPWTGPF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide
• IUPAC Traditional name: 1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(piperidin-1-yl)pyrazole-3-carboxamide
• Synonyms: 1-(2,4-Dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide; NIDA-41020

Database IDs

• CAS Number: 502486-89-7
• MDL Number: MFCD08277026
• PubChem SID: 162247995
• PubChem CID: 11037861

CALCULATED PROPERTIES

• Acid pKa: 12.426502
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.1462154
• LogD (pH = 7.4): 5.146277
• Log P: 5.1462817
• Molar Refractivity: 124.4892 cm^3
• Polarizability: 49.106674 Å^3
• Polar Surface Area: 59.39 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ~16 mg/mL; H2O: insoluble
• Apperance: off-white solid

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H315-H319-H335
• GHS Precautionary statements: P261-P264-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C23H24Cl2N4O2

DETAILS

Sigma Aldrich - N8162

Biochem/physiol Actions
NIDA-41020 is a CB1 cannabinoid receptor antagonist. NIDA-41020 is structurally similar to Rimonabant, which is currently in clinical development. NIDA-41020 is less lipophilic; developed at NIDA as a potential radioligand for CB1 receptors, Ki = 4.1 nM [in comparison AM 251, AM 281, SR 141716 (Rimonabant) have Ki of 0.6, 4.5 and 1.8 nM respectively].