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E2031

Sigma-Aldrich

Eliprodil

≥98% (HPLC), powder

Synonym(s):

α-(4-Chlorophenyl)-4-[(4-fluorophenyl)methyl]-1-piperidineethanol, SL 820715

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About This Item

Empirical Formula (Hill Notation):
C20H23ClFNO
CAS Number:
119431-25-3
Molecular Weight:
347.85
MDL number:
MFCD00866651
UNSPSC Code:
12352200
PubChem Substance ID:
24277709
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear
H2O: insoluble

originator

Sanofi Aventis

storage temp.

2-8°C

SMILES string

OC(CN1CCC(CC1)Cc2ccc(F)cc2)c3ccc(Cl)cc3

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

InChI key

GGUSQTSTQSHJAH-UHFFFAOYSA-N

Gene Information

human ... GRIN2B(2904)
rat ... Adra1a(29412)

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.

Features and Benefits

This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Csaba Lengyel et al.
British journal of pharmacology, 143(1), 152-158 (2004-08-11)
1. The aim of this study was to analyse the effects of eliprodil, a noncardiac drug with neuroprotective properties, on the cardiac repolarisation under in vitro circumstances, under normal conditions and after the attenuation of the 'repolarisation reserve' by blocking
J Pabel et al.
Bioorganic & medicinal chemistry letters, 10(12), 1377-1380 (2000-07-13)
A short synthesis of the NMDA receptor antagonist (rac)-Eliprodil (9) and its resolution into the enantiomers by chiral HPLC is described. The enantiomers (R)-9 and (S)-9 were found to exhibit markedly different affinities for NR2B subunit containing NMDA receptors.
S Hogg et al.
Journal of neurotrauma, 15(7), 545-553 (1998-07-23)
We have previously demonstrated that a lateral fluid percussion-induced traumatic lesion of the right parietal cortex can lead to a deficit in a conditioned freezing response and that this deficit can be attenuated by both pre- and postlesion administration of
C Demerens et al.
Neurology, 52(2), 346-350 (1999-02-05)
To examine the potential of eliprodil-a neuroprotective agent with a high affinity for sigma-receptors-to promote myelination in neuron-oligodendrocytes cocultures. Remyelination is one of the major therapeutic issues in MS. Because neuronal integrity is required for CNS myelination, the authors postulated
I H Pang et al.
Investigative ophthalmology & visual science, 40(6), 1170-1176 (1999-05-11)
To test whether eliprodil (SL 82.0715), a unique antagonist for the N-methyl-D-aspartate (NMDA) receptor, is protective in the glutamate-induced cytotoxicity model in cultured rat retinal ganglion cells (RGCs). Two to four days after a fluorescent dye, Di-I, was injected near
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