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Biological Data
| Biological description | Ifenprodil is a non-competitive, voltage-independent GluN2B subunit selective NMDA receptor allosteric inhibitor (IC50 = 0.15 μM).
It is selective over GluN2A (NR2A), GluN2C (NR2C) and GluN2D (NR2D) subunits (IC50 values are >30 μM).
Ifenprodil is thought to bind at the interface of the GluN1/2B NTD (ATD) (N-terminal domain).
Ifenprodil is commonly used to distinguish between GluN2B- and GluN2A- containing NMDARs in synaptic and extrasynaptic membranes.
Ifenprodil also shows use dependence in which binding of glutamate increases binding of ifenprodil and vice versa.
Shows neuroprotective effects and protects neurons against glutamate excitotoxicity in an activity-dependent manner.
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Solubility & Handling
| Storage instructions | Room temperature |
| Solubility overview | Soluble in water (15mM, gentle warming) |
| Important | This product is for RESEARCH USE ONLY and is not intended for therapeutic or diagnostic use. Not for human or veterinary use. |
Chemical Data
| Chemical name | (1R*,2S*)-erythro-2-(4-Benzylpiperidino)-1-(4-hydroxyphenyl)-1-propanol hemitartrate |
| Chemical structure | ![Ifenprodil [23210-58-4] Chemical Structure](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAQAAAC1HAwCAAAAC0lEQVR4nGP6zwAAAgcBApocMXEAAAAASUVORK5CYII= "Ifenprodil [23210-58-4]") |
| Molecular Formula | C21H27NO2.½C4H6O6 |
| PubChem identifier | 656586 |
| SMILES | CC(C(C1=CC=C(C=C1)O)O)N2CCC(CC2)CC3=CC=CC=C3.CC(C(C1=CC=C(C=C1)O)O)N2CCC(CC2)CC3=CC=CC=C3.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O |
| InChi | InChI=1S/2C21H27NO2.C4H6O6/c2*1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17;5-1(3(7)8)2(6)4(9)10/h2*2-10,16,18,21,23-24H,11-15H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t;;1-,2-/m..1/s1 |
| InChiKey | DMPRDSPPYMZQBT-CEAXSRTFSA-N |
References for Ifenprodil
References are publications that support the biological activity of the product
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Age and activation determines the anticonvulsant effect of ifenprodil in rats.
Mareš P (2014) Naunyn Schmiedebergs Arch Pharmacol 387(8) : 753-61. -
Ifenprodil effects on GluN2B-containing glutamate receptors.
Amico-Ruvio SA et al (2012) Mol Pharmacol 82(6) : 1074-81. -
Ifenprodil, a novel NMDA receptor antagonist: site and mechanism of action.
Williams K (2001) Curr Drug Targets 2(3) : 285-98. -
Ifenprodil is a novel type of NMDA receptor antagonist: interaction with polyamines.
Reynolds IJ et al (1989) Mol Pharmacol 36(5) : 758-65.
Publications
These publications cite the use of Ifenprodil purchased from Hello Bio:
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Mechanisms Underlying Long-Term Synaptic Zinc Plasticity at Mouse Dorsal Cochlear Nucleus Glutamatergic Synapses
Vogler NW et al (2020) J Neurosci 40(26) : 4981-4996 -
Functional and pharmacological properties of triheteromeric GluN1/2B/2D NMDA receptors
Yi F et al (2019) J Physiol 597(22) : 5495-5514 -
Ligand binding domain interface: A tipping point for pharmacological agents binding with GluN1/2A subunit containing NMDA receptors
Bledsoe D et al (2019) Eur J Pharmacol 844 : 216-224 -
Properties of triheteromeric NMDA receptors containing two distinct GluN1 isoforms.
Yi et al (2018) Mol Pharmacol pii: mol.117.111427 : /mol.117.111427. [Epub ahead of -
Positive Modulatory Interactions of NMDA Receptor GluN1/2B Ligand Binding Domains Attenuate Antagonists Activity.
Bledsoe et al (2017) Front Pharmacol 8:229 : doi: 10.3389/fphar.2017.00229
Non-competitive GluN2B subunit selective NMDAR allosteric inhibitor
![Ifenprodil [23210-58-4] Chemical Structure](https://hellobio.com/media/catalog/product//h/b/hb0339.png "Ifenprodil [23210-58-4]")
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