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Submit ReviewIfenprodil hemitartrate
Description: Non-competitive NMDA antagonist; also σ ligand
Chemical Name: (1R*,2S*)-erythro-2-(4-Benzylpiperidino)-1-(4-hydroxyphenyl)-1-propanol hemi-(DL)-tartrate
Purity: ≥99% (HPLC)
Biological Activity for Ifenprodil hemitartrate
Ifenprodil hemitartrate is a NMDA receptor antagonist, acting at the polyamine site. Also an α-adrenergic vasodilator. σ2 ligand displaying about 3-fold selectivity over σ1 sites.
Technical Data for Ifenprodil hemitartrate
| M. Wt | 400.49 |
| Formula | C21H27NO2.½C4H6O6 |
| Storage | Store at RT |
| Purity | ≥99% (HPLC) |
| PubChem ID | 3689 |
| InChI Key | UYNVMODNBIQBMV-UHFFFAOYSA-N |
| Smiles | OC1=CC=C([C@H]([C@@H](N2CCC(CC3=CC=CC=C3)CC2)C)O)C=C1.OC4=CC=C([C@H]([C@@H](N5CCC(CC6=CC=CC=C6)CC5)C)O)C=C4.O=C([C@H]([C@@H](C(O)=O)O)O)O.OC7=CC=C([C@@H]([C@H](N8CCC(CC9=CC=CC=C9)CC8)C)O)C=C7.OC%10=CC=C([C@@H]([C@H](N%11CCC(CC%12=CC=CC=C%12)CC%11)C)O)C=C%10.O=C([C@@H]([C@H](C(O)=O)O)O)O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Ifenprodil hemitartrate
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 4 | 10 | |
| DMSO | 40.05 | 100 |
Preparing Stock Solutions for Ifenprodil hemitartrate
The following data is based on the product molecular weight 400.49. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.5 mL | 12.48 mL | 24.97 mL |
| 5 mM | 0.5 mL | 2.5 mL | 4.99 mL |
| 10 mM | 0.25 mL | 1.25 mL | 2.5 mL |
| 50 mM | 0.05 mL | 0.25 mL | 0.5 mL |
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Product Datasheets for Ifenprodil hemitartrate
References for Ifenprodil hemitartrate
References are publications that support the biological activity of the product.
Gotti et al (1988) Ifenprodil and SL-82,0715 as cerebral anti-ischemic agents. 1. Evidence for efficacy in models of focal cerebral ischemia. J.Pharmacol.Exp.Ther. 247 1211 PMID: 2849668
Schoemaker et al (1990) Polyamine-sensitive binding of [3H]ifenprodil, a novel NMDA antagonist to the rat cerebral cortex. Eur.J.Pharmacol. 176 249 PMID: 2178949
Reynolds and Miller (1989) Ifenprodil is a novel type of N-MthD.-aspartate receptor antagonist: interaction with polyamines. Mol.Pharmacol. 36 758 PMID: 2555674
Shalaby et al (1992) Neuroprotective effects of the N-MthD.-aspartate receptor antagonists ifenprodil and SL-82,0715 on hippocampal cells in culture. J.Pharmacol.Exp.Ther. 260 925 PMID: 1346650
If you know of a relevant reference for Ifenprodil hemitartrate, please let us know.
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Keywords: Ifenprodil hemitartrate, Ifenprodil hemitartrate supplier, σ, sigma, ligand, σ2, sigma2, σ1, sigma1, α1-adrenoceptor, alpha1-adrenoceptor, a1-adrenoceptor, α1-adrenergic, alpha1-adrenergic, a1-adrenergic, antagonists, NMDA, polyamine, site, Receptors, Glutamate, N-Methyl-D-Aspartate, iGluR, Ionotropic, 23210-5, Adrenergic, Alpha-1, Sigma2, 0545, Tocris Bioscience
32 Citations for Ifenprodil hemitartrate
Citations are publications that use Tocris products. Selected citations for Ifenprodil hemitartrate include:
Galvez et al (2016) Activation of α7 nicotinic acetylcholine receptors protects potentiated synapses from depotentiation during theta pattern stimulation in the hippocampal CA1 region of rats. Neuropharmacology 105 378 PMID: 26867505
Dolma et al (2016) Inhibition of Dopamine Receptor D4 Impedes Autophagic Flux, Proliferation, and Survival of Glioblastoma Stem Cells. Cancer Cell 29 859 PMID: 27300435
Hedegaard et al (2012) Molecular pharmacology of human NMDA receptors. Neurochem Int 61 601 PMID: 22197913
Heinrich et al (2012) K+ depolarization evokes ATP, adenosine and glutamate release from glia in rat hippocampus: a microelectrode biosensor study. Br J Pharmacol 167 1003 PMID: 22394324
Gourley et al (2012) Arg kinase regulates prefrontal dendritic spine refinement and cocaine-induced plasticity. J Neurosci 32 2314 PMID: 22396406
Gaamouch et al (2012) Interaction between αCaMKII and GluN2B controls ERK-dependent plasticity. J Neurosci 32 10767 PMID: 22855824
Wills et al (2012) GluN2B subunit deletion reveals key role in acute and chronic ethanol sensitivity of glutamate synapses in bed nucleus of the stria terminalis. Proc Natl Acad Sci U S A 109 E278 PMID: 22219357
Higley and Sabatini (2010) Competitive regulation of synaptic Ca2+ influx by D2 DA and A2A adenosine receptors. Nat Neurosci 13 958 PMID: 20601948
McKay et al (2018) The Developmental Shift of NMDA Receptor Composition Proceeds Independently of GluN2 Subunit-Specific GluN2 C-Terminal Sequences. Cell Rep 25 841 PMID: 30355491
Brady et al (2013) Moderate prenatal alcohol exposure reduces plasticity and alters NMDA receptor subunit composition in the dentate gyrus. Int J Neuropsychopharmacol 33 1062 PMID: 23325244
Grochowska et al (2017) Posttranslational modification impact on the mechanism by which amyloid-β induces synaptic dysfunction. EMBO Rep 18 962 PMID: 28420656
Simma et al (2014) NMDA-receptor antagonists block B-cell function but foster IL-10 production in BCR/CD40-activated B cells. Cell Commun Signal 12 75 PMID: 25477292
Thomazeau et al (2014) Prefrontal deficits in a murine model overexpressing the down syndrome candidate gene dyrk1a. J Neurosci 34 1138 PMID: 24453307
Fontaine et al (2008) Vulnerability of white matter towards antenatal hypoxia is linked to a species-dependent regulation of glutamate receptor subunits. Dev Neurobiol 105 16779 PMID: 18922769
Popp et al (2008) Cerebellar granule cells cultured from adolescent rats express functional NMDA receptors: an in vitro model for studying the developing cerebellum. J Neurochem 106 900 PMID: 18466339
Regan et al (2019) Structural elements of a pH-sensitive inhibitor binding site in NMDA receptors. Nat Commun 10 321 PMID: 30659174
Kashima and Grueter (2017) Toll-like receptor 4 deficiency alters nucleus accumbens synaptic physiology and drug reward behavior. Proc Natl Acad Sci U S A. 114 8865 PMID: 28760987
Mirante et al (2014) Distinct molecular components for thalamic- and cortical-dependent plasticity in the lateral amygdala. J Neurosci 7 62 PMID: 25071439
Sánchez-Blázquez et al (2014) The calcium-sensitive σ-1 receptor prevents cannabinoids from provoking glutamate NMDA receptor hypofunction: implications in antinociception and psychotic diseases. Front Cell Neurosci 17 1943 PMID: 24485144
Roselli et al (2011) CDK5 is essential for soluble amyloid β-induced degradation of GKAP and remodeling of the synaptic actin cytoskeleton. PLoS One 6 e23097 PMID: 21829588
Zhang and Sun (2011) Development of NMDA NR2 subunits and their roles in critical period maturation of neocortical GABAergic interneurons. J Neurosci 71 221 PMID: 20936660
Yuan et al (2009) The serine protease plasmin cleaves the amino-terminal domain of the NR2A subunit to relieve zinc inhibition of the N-MthD.-aspartate receptors. J Biol Chem 284 12862 PMID: 19240037
Engelhardt et al (2015) GluN2D-containing NMDA receptors-mediate synaptic currents in hippocampal interneurons and pyramidal cells in juvenile mice. Proc Natl Acad Sci U S A 9 95 PMID: 25859181
McKay et al (2012) Direct pharmacological monitoring of the developmental switch in NMDA receptor subunit composition using TCN 213, a GluN2A-selective, glycine-dependent antagonist. Br J Pharmacol 166 924 PMID: 22022974
Shin et al (2005) The dextromethorphan analog dimemorfan attenuates kainate-induced seizures via sigma1 receptor activation: comparison with the effects of dextromethorphan. Br J Pharmacol 144 908 PMID: 15723099
Yang et al (2005) Behavioral stress enhances hippocampal CA1 long-term depression through the blockade of the glutamate uptake. PLoS One 25 4288 PMID: 15858055
Ning et al (2004) Dual neuroprotective signaling mediated by downregulating two distinct phosphatase activities of PTEN. J Neurosci 24 4052 PMID: 15102920
Amadoro et al (2006) NMDA receptor mediates tau-induced neurotoxicity by calpain and ERK/MAPK activation. Proc Natl Acad Sci U S A 103 2892 PMID: 16477009
Kopp et al (2006) Insufficient sleep reversibly alters bidirectional synaptic plasticity and NMDA receptor function. J Neurosci 26 12456 PMID: 17135407
Ge et al (2007) A critical period for enhanced synaptic plasticity in newly generated neurons of the adult brain. Neuron 54 559 PMID: 17521569
Nateri et al (2007) ERK activation causes epilepsy by stimulating NMDA receptor activity. EMBO J 26 4891 PMID: 17972914
Logan et al (2007) Long-lasting NMDA receptor-mediated EPSCs in mouse striatal medium spiny neurons. J Neurophysiol 98 2693 PMID: 17804581
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