Ifenprodil hemitartrate

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Cat.No. 0545 - Ifenprodil hemitartrate | C21H27NO2.½C4H6O6 | CAS No. 23210-58-4
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)
Datasheet
Citations (31)
Reviews
Literature (11)

Biological Activity

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

M. Wt 400.49
Formula C21H27NO2.½C4H6O6
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 23210-58-4
PubChem ID 3689
InChI Key UYNVMODNBIQBMV-UHFFFAOYSA-N
Smiles OC(C=C3)=CC=C3[C@@H](O)[C@H](C)N2CCC(CC2)CC1=CC=CC=C1.OC(C=C6)=CC=C6[C@@H](O)[C@H](C)N5CCC(CC5)CC4=CC=CC=C4.O=C(O)C(O)C(O)C(O)=O.OC(C=C9)=CC=C9[C@H](O)[C@@H](C)N8CCC(CC8)CC7=CC=CC=C7.OC(C=C%12)=CC=C%12[C@H](O)[C@@H](C)N%11CCC(CC%11)CC%10=CC=CC=C%10.O=C(O)C(O)C(O)C(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

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
water 6.01 15 with gentle warming

Preparing Stock Solutions

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
0.15 mM 16.65 mL 83.23 mL 166.46 mL
0.75 mM 3.33 mL 16.65 mL 33.29 mL
1.5 mM 1.66 mL 8.32 mL 16.65 mL
7.5 mM 0.33 mL 1.66 mL 3.33 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

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


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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

31 Citations for Ifenprodil hemitartrate

Citations are publications that use Tocris products. Selected citations for Ifenprodil hemitartrate include:

Regan et al (2019) Structural elements of a pH-sensitive inhibitor binding site in NMDA receptors. Nat Commun 10 321 PMID: 30659174

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

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

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

Grochowska et al (2017) Posttranslational modification impact on the mechanism by which amyloid-β induces synaptic dysfunction. EMBO Rep 18 962 PMID: 28420656

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

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

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

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

Logan et al (2007) Long-lasting NMDA receptor-mediated EPSCs in mouse striatal medium spiny neurons. J Neurophysiol 98 2693 PMID: 17804581

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

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

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

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

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

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


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