bis(oxalic acid); {2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethyl}(methyl)amine

• ChemBase ID: 154024
• Molecular Formular: C25H29N3O8
• Molecular Mass: 499.51306
• Monoisotopic Mass: 499.1954649
• SMILES: CNCCc1c[nH]c(n1)CCC(c1ccccc1)c1ccccc1.C(=O)(C(=O)O)O.C(=O)(C(=O)O)O
• Canonical SMILES: OC(=O)C(=O)O.OC(=O)C(=O)O.CNCCc1nc([nH]c1)CCC(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C21H25N3.2C2H2O4/c1-22-15-14-19-16-23-21(24-19)13-12-20(17-8-4-2-5-9-17)18-10-6-3-7-11-18;2*3-1(4)2(5)6/h2-11,16,20,22H,12-15H2,1H3,(H,23,24);2*(H,3,4)(H,5,6)
• InChIKey: ZKOVWJDRJCVMKH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(oxalic acid); {2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethyl}(methyl)amine
• IUPAC Traditional name: bis(oxalic acid); {2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethyl}(methyl)amine
• Synonyms: N-Methyl-2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]-ethanamine dioxalate salt; N-Methylhistaprodifen dioxalate salt; N-Methyl-2-[2-(3,3-diphenylpropyl)-1H-imidazol -4-yl]-ethanamine 二草酸盐; N-methylhistaprodifen 二草酸盐

Database IDs

• CAS Number: 270079-48-6
• MDL Number: MFCD09752603
• PubChem SID: 162248163
• PubChem CID: 51371166

CALCULATED PROPERTIES

• Acid pKa: 14.8162565
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.17609036
• LogD (pH = 7.4): 1.5358824
• Log P: 3.998974
• Molar Refractivity: 99.4462 cm^3
• Polarizability: 38.74068 Å^3
• Polar Surface Area: 40.71 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL; H2O: insoluble <2 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H25N3 · 2 C2H2O4

DETAILS

Sigma Aldrich - M7320

Biochem/physiol Actions
N-Methylhistaprodifen is more potent than histamine by a factor of 3.5 on guinea pig ileum; more potent than histamine by a factor of 4.3 on guinea pig arterial H1-receptor-mediated vasoconstriction; most potent H1-receptor agonist on the guinea pig ileum out of 17 agonists tested. pEC50 = 7.24 in contraction of guinea pig ileal whole segments; pEC50 = 6.31 in contraction of guinea pig aortic segments. N-methylhistaprodifen does not stimulate H2 and H3 histamine receptors; potential use in the study of H1-receptor-mediated physiological and pathophysiological functions.