Ifenprodil hemitartrate

Name: Ifenprodil hemitartrate
Brand: Tocris Bioscience
SKU: 0545

Tocris Bioscience a Bio-Techne Brand

Catalog # 0545

Citations (32)

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Key Product Details

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)
Molecular Weight:	400.49

View Full Technical Details for Ifenprodil hemitartrate

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 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	2.50 mL	12.48 mL	24.97 mL
5 mM	0.50 mL	2.50 mL	4.99 mL
10 mM	0.25 mL	1.25 mL	2.50 mL
50 mM	0.05 mL	0.25 mL	0.50 mL

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References for Ifenprodil hemitartrate

References are publications that support the biological activity of the product.

Shalaby Neuroprotective effects of the N-MthD.-aspartate receptor antagonists ifenprodil and SL-82,0715 on hippocampal cells in culture. J.Pharmacol.Exp.Ther. 1992 PMID: 1346650
Schoemaker Polyamine-sensitive binding of [³H]ifenprodil, a novel NMDA antagonist to the rat cerebral cortex. Eur.J.Pharmacol. 1990 PMID: 2178949
Reynolds and Miller Ifenprodil is a novel type of N-MthD.-aspartate receptor antagonist: interaction with polyamines. Mol.Pharmacol. 1989 PMID: 2555674
Gotti Ifenprodil and SL-82,0715 as cerebral anti-ischemic agents. 1. Evidence for efficacy in models of focal cerebral ischemia. J.Pharmacol.Exp.Ther. 1988 PMID: 2849668

Citations for Ifenprodil hemitartrate (32)

Showing 1 - 10 of 32 citations Showing All

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Citations are publications that use Bio-Techne 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
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
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(33):8865
PMID: 28760987
Grochowska et al. (2017) Posttranslational modification impact on the mechanism by which amyloid-β induces synaptic dysfunction. EMBO Rep. 18:962
PMID: 28420656
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
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
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
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
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
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
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
Gaamouch et al. (2012) Interaction between αCaMKII and GluN2B controls ERK-dependent plasticity. J Neurosci. 32:10767
PMID: 22855824
Gourley et al. (2012) Arg kinase regulates prefrontal dendritic spine refinement and cocaine-induced plasticity. J Neurosci. 32:2314
PMID: 22396406
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
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
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
Higley and Sabatini (2010) Competitive regulation of synaptic Ca²⁺ influx by D2 DA and A2A adenosine receptors. Nat Neurosci. 13:958
PMID: 20601948
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
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
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
Nateri et al. (2007) ERK activation causes epilepsy by stimulating NMDA receptor activity. EMBO J. 26:4891
PMID: 17972914
Ge et al. (2007) A critical period for enhanced synaptic plasticity in newly generated neurons of the adult brain. Neuron. 54:559
PMID: 17521569
Logan et al. (2007) Long-lasting NMDA receptor-mediated EPSCs in mouse striatal medium spiny neurons. J Neurophysiol. 98:2693
PMID: 17804581
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
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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