2-[(3-chlorophenyl)amino]-N-(pyridin-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide hydrochloride

• ChemBase ID: 154852
• Molecular Formular: C18H14Cl2F3N5O
• Molecular Mass: 444.2378696
• Monoisotopic Mass: 443.05275011
• SMILES: c1cc(cc(c1)Cl)Nc1ncc(c(n1)C(F)(F)F)C(=O)NCc1ccncc1.Cl
• Canonical SMILES: Clc1cccc(c1)Nc1ncc(c(n1)C(F)(F)F)C(=O)NCc1ccncc1.Cl
• InChI: InChI=1S/C18H13ClF3N5O.ClH/c19-12-2-1-3-13(8-12)26-17-25-10-14(15(27-17)18(20,21)22)16(28)24-9-11-4-6-23-7-5-11;/h1-8,10H,9H2,(H,24,28)(H,25,26,27);1H
• InChIKey: UBHSVFAUAKIVKL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3-chlorophenyl)amino]-N-(pyridin-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide hydrochloride
• IUPAC Traditional name: 2-[(3-chlorophenyl)amino]-N-(pyridin-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide hydrochloride
• Synonyms: 2-[(3-chlorophenyl)amino]-N-(4-pyridinylmethyl)-4-(trifluoromethyl)-5-Pyrimidinecarboxamide hydrochloride; GW833972A

Database IDs

• CAS Number: 1092502-33-4
• MDL Number: MFCD18452844
• PubChem SID: 162248990
• PubChem CID: 71312007

CALCULATED PROPERTIES

• Acid pKa: 12.019576
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.5076222
• LogD (pH = 7.4): 3.6156769
• Log P: 3.617308
• Molar Refractivity: 97.9918 cm^3
• Polarizability: 35.723846 Å^3
• Polar Surface Area: 79.8 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: off-white to light brown powder

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: H301-H315-H319-H335-H413
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H13ClF3N5O · HCl

DETAILS

Sigma Aldrich - G8173

Biochem/physiol Actions
GW833972A is a CB2 cannabinoid receptor agonist with 1000-fold selectivity relative to CB1. It is, however, 15-fold less potent than HU210 for CB2 (Ki 7.8 vs. 0.52 nM). The antitumor compound oxaliplatin induces marked hypersensitivity to cold, heat, and chemical pain stimuli (to the point where oxaliplatin therapy has to be discontinued). The hyperalgesia effect is almost completely blocked by pretreatment with GW833972A.1
GW833972A is a CB2 receptor agonist with 1000-fold selectivity relative to CB1. GW833972A is 15 fold less potent than HU210 for CB2 (Ki 7.8 vs. 0.52 nM). The compound was used to determine the role of CB2 in airway sensory nerve function.