4-[3-(4-cyclopropanecarbonylphenoxy)propyl]-1H-imidazole hydrochloride

• ChemBase ID: 153961
• Molecular Formular: C16H19ClN2O2
• Molecular Mass: 306.78726
• Monoisotopic Mass: 306.11350554
• SMILES: c1cc(ccc1C(=O)C1CC1)OCCCc1c[nH]cn1.Cl
• Canonical SMILES: O=C(c1ccc(cc1)OCCCc1nc[nH]c1)C1CC1.Cl
• InChI: InChI=1S/C16H18N2O2.ClH/c19-16(12-3-4-12)13-5-7-15(8-6-13)20-9-1-2-14-10-17-11-18-14;/h5-8,10-12H,1-4,9H2,(H,17,18);1H
• InChIKey: PWAPSKMHZQQTRJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[3-(4-cyclopropanecarbonylphenoxy)propyl]-1H-imidazole hydrochloride
• IUPAC Traditional name: 4-[3-(4-cyclopropanecarbonylphenoxy)propyl]-1H-imidazole hydrochloride
• Synonyms: Cyclopropyl[4-[3-(1H-imidazol-4-yl)propoxyl]phenyl]-methanone hydrochloride; Ciproxifan hydrochloride

Database IDs

• CAS Number: 1049741-81-2
• MDL Number: MFCD08705321
• PubChem SID: 24724449; 162248100
• PubChem CID: 16078963

CALCULATED PROPERTIES

• Acid pKa: 14.585167
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.5044147
• LogD (pH = 7.4): 2.2884722
• Log P: 2.3661673
• Molar Refractivity: 76.8228 cm^3
• Polarizability: 29.548162 Å^3
• Polar Surface Area: 54.98 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble30 mg/mL; water, high purity: soluble30 mg/mL
• Apperance: off-white solid

Safety Information

• Storage Condition: desiccated; under inert gas
• 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): C16H18N2O2 · HCl

DETAILS

Sigma Aldrich - C6492

Biochem/physiol Actions
Ciproxifan belongs to a novel chemical series of histamine H3-receptor antagonists. In vitro, it behaved as a competitive antagonist at the H3 autoreceptor controlling 3H histamine release from synaptosomes and displayed similar Ki values (0.5-1.9 nM) at the H3 receptor controlling the electrically-induced contraction of guinea pig ileum or at the brain H3 receptor labeled with 125I-iodoproxyfan. Ciproxifan appears to be an orally bioavailable, extremely potent and selective H3-receptor antagonist whose vigilance- and attention-promoting effects are promising for therapeutic applications in aging disorders.