1-(4-chlorophenyl)-2-{4-[(4-fluorophenyl)methyl]piperidin-1-yl}ethan-1-ol

• ChemBase ID: 153814
• Molecular Formular: C20H23ClFNO
• Molecular Mass: 347.8541232
• Monoisotopic Mass: 347.14522026
• SMILES: c1cc(ccc1CC1CCN(CC1)CC(c1ccc(cc1)Cl)O)F
• Canonical SMILES: Fc1ccc(cc1)CC1CCN(CC1)CC(c1ccc(cc1)Cl)O
• InChI: InChI=1S/C20H23ClFNO/c21-18-5-3-17(4-6-18)20(24)14-23-11-9-16(10-12-23)13-15-1-7-19(22)8-2-15/h1-8,16,20,24H,9-14H2
• InChIKey: GGUSQTSTQSHJAH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-chlorophenyl)-2-{4-[(4-fluorophenyl)methyl]piperidin-1-yl}ethan-1-ol
• IUPAC Traditional name: eliprodil
• Synonyms: α-(4-Chlorophenyl)-4-[(4-fluorophenyl)methyl]-1-piperidineethanol; SL 820715; Eliprodil

Database IDs

• CAS Number: 119431-25-3
• MDL Number: MFCD00866651
• PubChem SID: 24277709; 162247953
• PubChem CID: 60703

CALCULATED PROPERTIES

• Acid pKa: 14.069307
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.6087654
• LogD (pH = 7.4): 3.2526796
• Log P: 4.7468123
• Molar Refractivity: 96.971 cm^3
• Polarizability: 37.50059 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ~17 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H319-H410
• GHS Precautionary statements: P273-P305 + P351 + P338-P501
• Personal Protective Equipment: Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... GRIN2B(2904)rat ... Adra1a(29412)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H23ClFNO

DETAILS

Sigma Aldrich - E2031

Biochem/physiol Actions
NR2B selective NMDA glutamate receptor antagonist which appears to target the "polyamine site" on the NMDA receptor, setting it apart from other NR2B receptor antagonists. Possesses neuroprotective effects in models of ischemia, but prolongs the QT interval in patients; currently under investigation for acute and chronic pain.