Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C5H9NO4 |
| Molecular Weight | 147.1293 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN[C@H](CC(O)=O)C(O)=O
InChI
InChIKey=HOKKHZGPKSLGJE-GSVOUGTGSA-N
InChI=1S/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)/t3-/m1/s1
N-Methyl-D-aspartic acid is an amino acid derivative acting as a specific agonist at the NMDA receptor, and therefore mimics the action of the neurotransmitter glutamate on that receptor. Unlike glutamate, NMDA only binds to and regulates the NMDA receptor and has no effect on other glutamate receptors (such as those for AMPA and kainate). NMDA receptors are particularly important when they become overactive during withdrawal from alcohol as this causes symptoms such as agitation and, sometimes, epileptiform seizures. NMDA is a water-soluble synthetic substance that is not normally found in biological tissue.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Consolidation of transient ionotropic glutamate signals through nuclear transcription factors in the brain. | 2001-04 |
|
| Glycine reduces novelty- and methamphetamine-induced locomotor activity in neonatal ventral hippocampal damaged rats. | 2001-03 |
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| Differential and region-specific activation of mitogen-activated protein kinases following chronic administration of phencyclidine in rat brain. | 2001-03 |
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| Metabotropic and NMDA glutamate receptors participate in the cannabinoid-induced antinociception. | 2001-03 |
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| N-methyl-D-aspartate receptor antagonist reduces nitrotyrosine formation in caudate-putamen in rat focal cerebral ischemia-reperfusion. | 2001-02-16 |
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| Oxytocin enhances presynaptic and postsynaptic glutamatergic transmission between rat olfactory bulb neurones in culture. | 2001-02-16 |
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| Phencyclidine-induced discriminative stimulus is mediated via phencyclidine binding sites on the N-methyl-D-aspartate receptor-ion channel complex, not via sigma(1) receptors. | 2001-02-15 |
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| Use-dependent effects of amyloidogenic fragments of (beta)-amyloid precursor protein on synaptic plasticity in rat hippocampus in vivo. | 2001-02-15 |
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| Assembly with the NR1 subunit is required for surface expression of NR3A-containing NMDA receptors. | 2001-02-15 |
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| Laminar organization of the NMDA receptor complex within the postsynaptic density. | 2001-02-15 |
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| Deficits in the expression of the NR2B subunit in the hippocampus of aged Fisher 344 rats. | 2001-02-13 |
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| Effects of pharmacologically induced changes in NMDA-receptor activity on long-term memory in humans. | 2001-02-13 |
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| Application of N-methyl-D-aspartate induces long-term potentiation in the medial perforant path and long-term depression in the lateral perforant path of the rat dentate gyrus in vitro. | 2001-02-09 |
|
| Effect of graded hypoxia on the high-affinity CPP binding site of the NMDA receptor in the cerebral cortex of newborn piglets. | 2001-02-09 |
|
| Differential gene expression profiling in human brain tumors. | 2001-02-07 |
|
| Endogenous indoles as novel polyamine site ligands at the N-methyl-D-aspartate receptor complex. | 2001-02-02 |
|
| Potassium chloride depolarization mediates CREB phosphorylation in striatal neurons in an NMDA receptor-dependent manner. | 2001-02-02 |
|
| Atypical neural messengers. | 2001-02 |
|
| Glutamate receptor dysregulation in the hippocampus of transgenic mice carrying mutated human amyloid precursor protein. | 2001-02 |
|
| Selective blockade of the mGluR1 receptor reduces traumatic neuronal injury in vitro and improvesoOutcome after brain trauma. | 2001-02 |
|
| Changes in agonist concentration dependence that are a function of duration of exposure suggest N-methyl-D-aspartate receptor nonsaturation during synaptic stimulation. | 2001-02 |
|
| Glutamate 2000: old dog, new tricks. | 2001-02 |
|
| Pharmacological properties of the potent epileptogenic amino acid dysiherbaine, a novel glutamate receptor agonist isolated from the marine sponge Dysidea herbacea. | 2001-02 |
|
| Effect of adrenalectomy on membrane properties and synaptic potentials in rat dentate granule cells. | 2001-02 |
|
| Mu opiates inhibit long-term potentiation induction in the spinal cord slice. | 2001-02 |
|
| Orphenadrine prevents 3-nitropropionic acid-induced neurotoxicity in vitro and in vivo. | 2001-02 |
|
| Large-dose oral dextromethorphan as an adjunct to patient-controlled analgesia with morphine after knee surgery. | 2001-02 |
|
| Xenon inhibits but N(2)O enhances ketamine-induced c-Fos expression in the rat posterior cingulate and retrosplenial cortices. | 2001-02 |
|
| A murine model of opioid-induced hyperalgesia. | 2001-01-31 |
|
| Intraischemic but not postischemic hypothermia prevents non-selective hippocampal downregulation of AMPA and NMDA receptor gene expression after global ischemia. | 2001-01-31 |
|
| Antinociceptive effects after intrathecal administration of phosphodiester-, 2'-O-allyl-, and C-5-propyne-modified antisense oligodeoxynucleotides targeting the NMDAR1 subunit in mouse. | 2001-01-31 |
|
| Magnesium deprivation decreases cellular reduced glutathione and causes oxidative neuronal death in murine cortical cultures. | 2001-01-26 |
|
| NMDA receptor antagonist AP5 and nitric oxide synthase inhibitor 7-NI affect different phases of learning and memory in goldfish. | 2001-01-19 |
|
| Modeling of evoked field potentials in hippocampal CA1 area describes their dependence on NMDA and GABA receptors. | 2001-01-15 |
|
| Mitogen-activated protein kinase/extracellular signal-regulated kinase activation in somatodendritic compartments: roles of action potentials, frequency, and mode of calcium entry. | 2001-01-15 |
|
| Hyperfunction of dopaminergic and serotonergic neuronal systems in mice lacking the NMDA receptor epsilon1 subunit. | 2001-01-15 |
|
| Cytosolic calcium oscillations in astrocytes may regulate exocytotic release of glutamate. | 2001-01-15 |
|
| Quantitative relationship between transmitter release and calcium current at the calyx of held synapse. | 2001-01-15 |
|
| Three pairs of cysteine residues mediate both redox and zn2+ modulation of the nmda receptor. | 2001-01-15 |
|
| Cooperation of NMDA and tachykinin NK(1) and NK(2) receptors in the medullary transmission of vagal afferent input from the acid-threatened rat stomach. | 2001-01 |
|
| Old spines can't dance. | 2001-01 |
|
| The role of group I and group II metabotropic glutamate receptors in modulation of striatal NMDA and quinolinic acid toxicity. | 2001-01 |
|
| Reduced perisomatic inhibition, increased excitatory transmission, and impaired long-term potentiation in mice deficient for the extracellular matrix glycoprotein tenascin-R. | 2001-01 |
|
| Mutant huntingtin enhances excitotoxic cell death. | 2001-01 |
|
| Inhibition of spinal N-acetylated-alpha-linked acidic dipeptidase produces an antinociceptive effect in the rat formalin test. | 2001 |
|
| Glutamatergic regulation of haloperidol-induced c-fos expression in the rat striatum and nucleus accumbens. | 2001 |
|
| Muscarinic cholinergic and glutamatergic reciprocal regulation of expression of hippocampal cholinergic neurostimulating peptide precursor protein gene in rat hippocampus. | 2001 |
|
| Ca(2+) entry through L-type Ca(2+) channels helps terminate epileptiform activity by activation of a Ca(2+) dependent afterhyperpolarisation in hippocampal CA3. | 2001 |
|
| Temperature-dependent separation of a delayed-onset long-lasting enhancement mediated by coactivation of NMDA and metabotropic glutamate receptors following a transient exposure of extracellular high Ca(2+). | 2001 |
|
| Spreading depolarization waves triggered by vagal stimulation in the embryonic chick brain: optical evidence for intercellular communication in the developing central nervous system. | 2001 |
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DSLD |
1787 (Number of products:10)
Created by
admin on Mon Mar 31 22:58:43 GMT 2025 , Edited by admin on Mon Mar 31 22:58:43 GMT 2025
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| Code System | Code | Type | Description | ||
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N-Methyl-D-aspartic acid
Created by
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6384-92-5
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22880
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m8019
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PRIMARY | Merck Index | ||
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6121
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31882
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1903B9Q6PI
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DTXSID8041082
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ACTIVE MOIETY
