Eliprodil

Base Information

• Chemical Name: Eliprodil
• CAS No.: 119431-25-3
• Molecular Formula: C₂₀H₂₃ClFNO
• Molecular Weight: 347.86
• Hs Code.: 2933399090
• European Community (EC) Number: 634-251-8
• UNII: YW62A6TW29
• DSSTox Substance ID: DTXSID1045744
• Wikipedia: Eliprodil
• Wikidata: Q5361298
• NCI Thesaurus Code: C80994
• Pharos Ligand ID: SW5FHKRZ53BC
• Metabolomics Workbench ID: 153770
• ChEMBL ID: CHEMBL28564
• Mol file: 119431-25-3.mol

Synonyms:(4-chlorophenyl)-4-((4-fluorophenyl)methyl)-1-piperidineethanol;eliprodil;SL 82-0715;SL 82.0715;SL-820715

Chemical Property of Eliprodil

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 8.57E-10mmHg at 25°C
• Boiling Point: 474.1 °C at 760 mmHg
• PKA: 13.99±0.20(Predicted)
• Flash Point: 240.5 °C
• PSA: 23.47000
• Density: 1.205 g/cm³
• LogP: 4.40510
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ~17 mg/mL
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 347.1452202
• Heavy Atom Count: 24
• Complexity: 359

Purity/Quality:

97% ^*data from raw suppliers

Eliprodil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN(CCC1CC2=CC=C(C=C2)F)CC(C3=CC=C(C=C3)Cl)O
• Recent ClinicalTrials: Treatment of Parkinson's Disease With Eliprodil
• Description: N-Methyl-D-aspartate (NMDA) receptors are calcium permeable ligand-gated channels of the central nervous system that are activated after binding of the co-agonists glutamate and glycine. Eliprodil is a non-competitive NMDA receptor antagonist that inhibits neuronal calcium channel currents. It is selective for NR2B subunit-containing receptors (IC50 = 1 μM), displaying greater than 100-fold selectivity for NR2B over NR2A and NR2C subunits. Eliprodil also avidly binds σ1 and σ2 sites (Kis = 0.013 and 0.63 μM, respectively). It is effective in vivo, blocking ischemia-induced neurodegeneration in the CA1 region of the hippocampus of gerbils subjected to bilateral carotid artery occlusion. Eliprodil can also have proarrhythmic actions in hearts under normal conditions.
• Uses: Eliprodil is a noncardiac drug with neuroprotective properties. It is also a N-Methyl-D-aspartate receptor (NMDAR) antagonist.

Technology Process of Eliprodil

There total 10 articles about Eliprodil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

1-(4-chlorophenyl)-2-[4-(4-fluorobenzyl)-piperidin-1-yl]ethanon (291773-74-5) → (+)-Eliprodil (119431-25-3) + R-(-)-α-(4-chlorophenyl)-4-[(4-fluorophenyl)methyl]piperidine-1-ethanol (119431-25-3)

Guidance literature:

1-(4-chlorophenyl)-2-[4-(4-fluorobenzyl)-piperidin-1-yl]ethanon; With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 3h;

Chiralpak AD HPLC column;

DOI:10.1016/S0960-894X(00)00246-8

Reference yield: 76.0%

1-(4-chlorophenyl)-2-[4-(4-fluorobenzyl)-piperidin-1-yl]ethanon (291773-74-5) → (+)-Eliprodil (119431-25-3) + R-(-)-α-(4-chlorophenyl)-4-[(4-fluorophenyl)methyl]piperidine-1-ethanol (119431-25-3)

Guidance literature:

1-(4-chlorophenyl)-2-[4-(4-fluorobenzyl)-piperidin-1-yl]ethanon; With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 3h;

Chiralpak AD HPLC column;

DOI:10.1016/S0960-894X(00)00246-8

Reference yield: 76.0%

1-(4-chlorophenyl)-2-[4-(4-fluorobenzyl)-piperidin-1-yl]ethanon (291773-74-5) → eliprodil (119431-25-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 3h;

DOI:10.1016/S0960-894X(00)00246-8

upstream raw materials:

1-(4-chlorophenyl)-2-[4-(4-fluorobenzyl)-piperidin-1-yl]ethanon

4-(4-fluorobenzyl)piperidine hydrochloride

4-chlorobenzoylmethyl bromide