(+)-MK 801 maleate

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Cat.No. 0924 - (+)-MK 801 maleate | C16H15N.C4H4O4 | CAS No. 77086-22-7
Description: Non-competitive NMDA antagonist; acts at ion channel site
Alternative Names: Dizocilpine
Chemical Name: (5S,10R)-(+)-5-Methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine maleate
Purity: ≥99% (HPLC)
Datasheet
Citations (89)
Reviews
Literature

Biological Activity

A potent, selective and non-competitive NMDA receptor antagonist. Acts by binding to a site located within the NMDA associated ion channel and thus prevents Ca2+ flux. An effective anti-ischemic agent in several animal models.

Available as part of the Mixed NMDA Receptor Tocriset™. (-)-enantiomer also available.

Compound Libraries

(+)-MK 801 maleate is also offered as part of the Tocriscreen Plus. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 337.37
Formula C16H15N.C4H4O4
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 77086-22-7
PubChem ID 6420042
InChI Key QLTXKCWMEZIHBJ-PJGJYSAQSA-N
Smiles O=C(O)/C=C\C(O)=O.C[C@]1(N4)C3=C(C=CC=C3)C[C@@H]4C2=C1C=CC=C2

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 8.43 25
DMSO 33.74 100

Preparing Stock Solutions

The following data is based on the product molecular weight 337.37. 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 2.96 mL 14.82 mL 29.64 mL
5 mM 0.59 mL 2.96 mL 5.93 mL
10 mM 0.3 mL 1.48 mL 2.96 mL
50 mM 0.06 mL 0.3 mL 0.59 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.

Gill et al (1991) The neuroprotective action of dizocilpine (MK-801) in the rat middle cerebral artery occlusion model of focal ischaemia. Br.J.Pharmacol. 103 2030 PMID: 1912992

Hatfield et al (1992) The dose-response relationship and therapeutic window for dizocilpine (MK-801) in a rat focal ischaemia model. Eur.J.Pharmacol. 216 1 PMID: 1526248

Wong et al (1986) The anticonvulsant MK 801 is a potent N-MthD.-aspartate antagonist. Proc.Natl.Acad.Sci.U.S.A. 83 7104 PMID: 3529096

Zajaczkowski et al (1997) Uncompetitive NMDA receptor antagonists attenuate NMDA-induced impairment of passive avoidance learning and LTP. Neuropharmacology 36 961 PMID: 9257940


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89 Citations for (+)-MK 801 maleate

Citations are publications that use Tocris products. Selected citations for (+)-MK 801 maleate include:

Zou et al (2015) Oligodendrocytes Are Targets of HIV-1 Tat: NMDA and AMPA Receptor-Mediated Effects on Survival and Development. J Neurosci 35 11384 PMID: 26269645

Parnaudeau et al (2014) Glucocorticoid receptor gene inactivation in DA-innervated areas selectively decreases behavioral responses to amphetamine. Front Behav Neurosci 8 35 PMID: 24574986

Deléglise et al (2014) β-amyloid induces a dying-back process and remote trans-synaptic alterations in a microfluidic-based reconstructed neuronal network. Acta Neuropathol Commun 2 145 PMID: 25253021

Tamburri et al (2013) NMDA-receptor activation but not ion flux is required for amyloid-β induced synaptic depression. PLoS One 8 e65350 PMID: 23750255

Tsunekawa et al (2013) Enhanced expression of WD repeat-containing protein 35 (WDR35) stimulated by domoic acid in rat hippocampus: involvement of reactive oxygen species generation and p38 mitogen-activated protein kinase activation. J Neuroinflammation 14 4 PMID: 23289926

Straub et al (2011) Distinct functions of kainate receptors in the brain are determined by the auxiliary subunit Neto1. Nat Neurosci 14 866 PMID: 21623363

Chen et al (2007) PREGS induces LTP in the hippocampal dentate gyrus of adult rats via the tyrosine phosphorylation of NR2B coupled to ERK/CREB [corrected] signaling. J Neurophysiol 98 1538 PMID: 17625058

Philippart et al (2016) Differential Somatic Ca2+ Channel Profile in Midbrain DArgic Neurons The Journal of Neuroscience 6 7234 PMID: 27383597

Freitas et al (2016) Glutathione-Induced Calcium Shifts in Chick Retinal Glial Cells. PLoS One 11 e0153677 PMID: 27078878

Kaufman et al (2012) Opposing roles of synaptic and extrasynaptic NMDA receptor signaling in cocultured striatal and cortical neurons. FASEB J 32 3992 PMID: 22442066

Brager and Johnston (2007) Plasticity of intrinsic excitability during long-term depression is mediated through mGluR-dependent changes in I(h) in hippocampal CA1 pyramidal neurons. J Neurosci 27 13926 PMID: 18094230

Joo et al (2007) Activation of NMDA receptors increases proliferation and differentiation of hippocampal neural progenitor cells. J Cell Sci 120 1358 PMID: 17389682

Steward et al (2007) A form of perforant path LTP can occur without ERK1/2 phosphorylation or immediate early gene induction. Learn Mem 14 433 PMID: 17562895

Albright et al (2007) Increased thalamocortical synaptic response and decreased layer IV innervation in GAP-43 knockout mice. J Neurophysiol 98 1610 PMID: 17581849

O'Donnell et al (2016) Transient Oxygen/Glucose Deprivation Causes a Delayed Loss of Mitochondria and Increases Spontaneous Calcium Signaling in Astrocytic Processes. J Neurosci 36 7109 PMID: 27383588

Gaamouch et al (2012) Interaction between αCaMKII and GluN2B controls ERK-dependent plasticity. J Neurosci 32 10767 PMID: 22855824

Kocsis (2012) State-dependent increase of cortical gamma activity during REM sleep after selective blockade of NR2B subunit containing NMDA receptors. Sleep 35 1011 PMID: 22754048

Pedrazzi et al (2012) Potentiation of NMDA receptor-dependent cell responses by extracellular high mobility group box 1 protein. PLoS One 7 e44518 PMID: 22952988

Lee and Sherman (2012) Intrinsic modulators of auditory thalamocortical transmission. Hear Res 287 43 PMID: 22726616

Cassé et al (2012) Glutamate controls tPA recycling by astrocytes, which in turn influences glutamatergic signals. J Neurosci 32 5186 PMID: 22496564

Rodríguez-Muñoz et al (2012) The mu-opioid receptor and the NMDA receptor associate in PAG neurons: implications in pain control. Neuropsychopharmacology 37 338 PMID: 21814188

Léveillé et al (2010) Suppression of the intrinsic apoptosis pathway by synaptic activity. J Neurosci 30 2623 PMID: 20164347

Shin et al (2006) Vasoconstrictive neurovascular coupling during focal ischemic depolarizations. J Cereb Blood Flow Metab 26 1018 PMID: 16340958

González-Rueda et al (2018) Activity-Dependent Downscaling of Subthreshold Synaptic Inputs during Slow-Wave-Sleep-like Activity In Vivo. Neuron 97 1244 PMID: 29503184

Sánchez-Blázquez et al (2018) Sigma 1 Receptor Antagonists Inhibit Manic-Like Behaviors in Two Congenital Strains of Mice. Int J Neuropsychopharmacol 21 938 PMID: 29860313

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

Lim et al (2018) Neuronal Activity-Dependent Activation of Astroglial Calcineurin in Mouse Primary Hippocampal Cultures. Int J Mol Sci 19 PMID: 30274399

Marinangeli et al (2018) AMP-Activated Protein Kinase Is Essential for the Maintenance of Energy Levels during Synaptic Activation. iScience 9 1 PMID: 30368077

Kamiya et al (2018) Electrophysiological measurement of ion channels on plasma/organelle membranes using an on-chip lipid bilayer system. Sci Rep 8 17498 PMID: 30504856

Rojas et al (2013) Activation of group I metabotropic glutamate receptors potentiates heteromeric kainate receptors. Mol Pharmacol 83 106 PMID: 23066089

Koeglsperger et al (2013) Impaired glutamate recycling and GluN2B-mediated neuronal calcium overload in mice lacking TGF-β1 in the CNS. Glia 61 985 PMID: 23536313

Bengtson et al (2013) Calcium responses to synaptically activated bursts of action potentials and their synapse-independent replay in cultured networks of hippocampal neurons. Biochim Biophys Acta 1833 1672 PMID: 23360982

Gerstner et al (2005) Glutaric acid and its metabolites cause apoptosis in immature oligodendrocytes: a novel mechanism of white matter degeneration in glutaryl-CoA dehydrogenase deficiency. Pediatr Res 57 771 PMID: 15774829

Dubovyk et al (2018) Time-dependent alterations in the expression of NMDA receptor subunits along the dorsoventral hippocampal axis in an animal model of nascent psychosis. ACS.Chem.Neurosci. 9 2241 PMID: 29634239

Schitine et al (2015) Functional plasticity of GAT-3 in avian Müller cells is regulated by neurons via a glutamatergic input. PLoS One 82 42 PMID: 25700791

Rodríguez-Muñoz et al (2015) The ON:OFF switch, σ1R-HINT1 protein, controls GPCR-NMDA receptor cross-regulation: implications in neurological disorders. Int J Neuropsychopharmacol 6 35458 PMID: 26461475

Chintala et al (2015) Decreased Expression of DREAM Promotes the Degeneration of Retinal Neurons. Front Aging Neurosci 10 e0127776 PMID: 26020793

Zhang et al (2015) Miro1 deficiency in amyotrophic lateral sclerosis. Cell Death Dis 7 100 PMID: 26074815

Bertrand et al (2015) Conformations of tissue plasminogen activator (tPA) orchestrate neuronal survival by a crosstalk between EGFR and NMDAR. Cell Death Dis 6 e1924 PMID: 26469972

Birnbaum et al (2015) Calcium flux-independent NMDA receptor activity is required for Aβ oligomer-induced synaptic loss. J Clin Invest 6 e1791 PMID: 26086964

Cipriani et al (2015) FTY720 attenuates excitotoxicity and neuroinflammation. Curr Mol Med 12 86 PMID: 25953296

Kato et al (2015) Neurobehavioral Differences Between Mice Receiving Distinct Neuregulin Variants as Neonates; Impact on Sensitivity to MK-801. Cell Death Dis 15 222 PMID: 25817857

Curcio et al (2015) Brain ischemia downregulates the neuroprotective GDNF-Ret signaling by a calpain-dependent mechanism in cultured hippocampal neurons. J Neurosci 6 e1645 PMID: 25675305

Stephen et al (2015) Miro1 Regulates Activity-Driven Positioning of Mitochondria within Astrocytic Processes Apposed to Synapses to Regulate Intracellular Calcium Signaling. Front Behav Neurosci 35 15996 PMID: 26631479

Grüter et al (2015) Altered neuronal excitability underlies impaired hippocampal function in an animal model of psychosis. J Biol Chem 9 117 PMID: 26042007

Wang et al (2015) MFN2 couples glutamate excitotoxicity and mitochondrial dysfunction in motor neurons. Nat Commun 290 168 PMID: 25416777

Baxter et al (2015) Synaptic NMDA receptor activity is coupled to the transcriptional control of the glutathione system. Neuroscience 6 6761 PMID: 25854456

Quillinan et al (2015) Region-specific role for GluN2B-containing NMDA receptors in injury to Purkinje cells and CA1 neurons following global cerebral ischemia. Neuropharmacology 284 555 PMID: 25450957

Velásquez-Martínez et al (2015) α-1 adrenoreceptors modulate GABA release onto ventral tegmental area DA neurons. BMC Neurosci 88 110 PMID: 25261018

Naka et al (2013) Non-Hebbian plasticity at C-fiber synapses in rat spinal cord lamina I neurons. Pain 154 1333 PMID: 23707311

Pasquale and Sherman (2013) A modulatory effect of the feedback from higher visual areas to V1 in the mouse. J Neurophysiol 109 2618 PMID: 23446698

Jarzylo and Man (2012) Parasynaptic NMDA receptor signaling couples neuronal glutamate transporter function to AMPA receptor synaptic distribution and stability. J Neurosci 32 2552 PMID: 22396428

Laricchiuta et al (2012) Differences in spontaneously avoiding or approaching mice reflect differences in CB1-mediated signaling of dorsal striatal transmission. PLoS One 7 e33260 PMID: 22413007

Rossi et al (2012) Interleukin-1β causes anxiety by interacting with the endocannabinoid system. J Neurosci 32 13896 PMID: 23035099

Blouet and Schwartz (2012) Duodenal lipid sensing activates vagal afferents to regulate non-shivering brown fat thermogenesis in rats. PLoS One 7 e51898 PMID: 23251649

Carlson et al (2012) Pharmacological evidence that D-aspartate activates a current distinct from ionotropic glutamate receptor currents in Aplysia californica. Brain Behav 2 391 PMID: 22950043

Peterfi et al (2012) Endocannabinoid-mediated long-term depression of afferent excitatory synapses in hippocampal pyramidal cells and GABAergic interneurons. J Neurosci 32 14448 PMID: 23055515

Kim et al (2012) Decreased afferent excitability contributes to synaptic depression during high-frequency stimulation in hippocampal area CA1. J Neurophysiol 108 1965 PMID: 22773781

Chang et al (2010) Rapid activation of dormant presynaptic terminals by phorbol esters. J Neurosci 30 10048 PMID: 20668189

Talpalar and Kiehn (2010) Glutamatergic mechanisms for speed control and network operation in the rodent locomotor CpG. Front Neural Circuits 4 PMID: 20844601

Calò et al (2005) Interactions between ephrin-B and metabotropic glutamate 1 receptors in brain tissue and cultured neurons. J Neurosci 25 2245 PMID: 15745950

Shleper et al (2005) D-serine is the dominant endogenous coagonist for NMDA receptor neurotoxicity in organotypic hippocampal slices. Nature 25 9413 PMID: 16221850

Liot et al (2004) 2,7-Bis-(4-amidinobenzylidene)-cycloheptan-1-one dihydrochloride, tPA stop, prevents tPA-enhanced excitotoxicity both in vitro and in vivo. Proc Natl Acad Sci U S A 24 1153 PMID: 15529015

Tongiorgi et al (2004) Brain-derived neurotrophic factor mRNA and protein are targeted to discrete dendritic laminas by events that trigger epileptogenesis. J Neurosci 24 6842 PMID: 15282290

Klug et al (2012) Genetic inhibition of CaMKII in dorsal striatal medium spiny neurons reduces functional excitatory synapses and enhances intrinsic excitability. PLoS One 7 e45323 PMID: 23028932

Fallarini et al (2009) Clovamide and rosmarinic acid induce neuroprotective effects in in vitro models of neuronal death. Br J Pharmacol 157 1072 PMID: 19466982

Gabriel et al (2003) Transforming growth factor alpha-induced expression of type 1 plasminogen activator inhibitor in astrocytes rescues neurons from excitotoxicity. FASEB J 17 277 PMID: 12490542

Valable et al (2003) Angiopoietin-1-induced PI3-kinase activation prevents neuronal apoptosis. Oncotarget 17 443 PMID: 12514118

Chen et al (2002) Development of a human neuronal cell model for human immunodeficiency virus (HIV)-infected macrophage-induced neurotoxicity: apoptosis induced by HIV type 1 primary isolates and evidence for involvement of the Bcl-2/Bcl-xL-sensitive intrinsic apoptosis pa J Virol 76 9407 PMID: 12186923

Rzeski et al (2001) Glutamate antagonists limit tumor growth. J Neurosci 98 6372 PMID: 11331750

Musella (2017) A novel crosstalk within the endocannabinoid system controls GABA transmission in the striatum. Sci Rep 7 7363 PMID: 28779174

Owen and Grover (2015) Activity-dependent differences in function between proximal and distal Schaffer collaterals. J Neurophysiol 113 3646 PMID: 25855695

Wang et al (2015) Rewarding Effects of Optical Stimulation of Ventral Tegmental Area Glutamatergic Neurons. J Neurosci 35 15948 PMID: 26631475

Pan et al (2014) Deranged NMDAergic cortico-subthalamic transmission underlies parkinsonian motor deficits. J Neuroinflammation 124 4629 PMID: 25202982

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. Neurochem Int 17 1943 PMID: 24485144

Mirante et al (2014) Distinct molecular components for thalamic- and cortical-dependent plasticity in the lateral amygdala. J Neurosci 7 62 PMID: 25071439

Vicente-Sánchez et al (2013) HINT1 protein cooperates with cannabinoid 1 receptor to negatively regulate glutamate NMDA receptor activity. Mol Brain 6 42 PMID: 24093505

Lundgaard et al (2013) Neuregulin and BDNF induce a switch to NMDA receptor-dependent myelination by oligodendrocytes. PLoS Biol 11 e1001743 PMID: 24391468

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

Lecrux et al (2011) Pyramidal neurons are "neurogenic hubs" in the neurovascular coupling response to whisker stimulation. J Neurosci 31 9836 PMID: 21734275

Chao et al (2009) Na+ mechanism of delta-opioid receptor induced protection from anoxic K+ leakage in the cortex. Cell Mol Life Sci 66 1105 PMID: 19189047

Roselli et al (2009) Disassembly of shank and homer synaptic clusters is driven by soluble beta-amyloid(1-40) through divergent NMDAR-dependent signalling pathways. PLoS One 4 e6011 PMID: 19547699

Gielen et al (2009) Mechanism of differential control of NMDA receptor activity by NR2 subunits. J Cereb Blood Flow Metab 459 703 PMID: 19404260

Matthies et al (2000) Enhancement of glutamate release by L-fucose changes effects of glutamate receptor antagonists on long-term potentiation in the rat hippocampus. Learn Mem 7 227 PMID: 10940323

Brancaccio et al (2017) Astrocytes Control Circadian Timekeeping in the Suprachiasmatic Nucleus via Glutamatergic Signaling. Neuron 93 1420 PMID: 28285822

Iwasato et al (2008) Cortical adenylyl cyclase 1 is required for thalamocortical synapse maturation and aspects of layer IV barrel development. J Neurosci 28 5931 PMID: 18524897

Pais et al (2008) Necrotic neurons enhance microglial neurotoxicity through induction of glutaminase by a MyD88-dependent pathway. J Neurosci 5 43 PMID: 18844999

Léveillé et al (2008) Neuronal viability is controlled by a functional relation between synaptic and extrasynaptic NMDA receptors. FASEB J 22 4258 PMID: 18711223

Furness et al (2008) A quantitative assessment of glutamate uptake into hippocampal synaptic terminals and astrocytes: new insights into a neuronal role for excitatory amino acid transporter 2 (EAAT2). Neuroscience 157 80 PMID: 18805467


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