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
| Molecular Formula | C5H9NO4 |
| Molecular Weight | 147.1293 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| 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 |
|
| Consolidation of transient ionotropic glutamate signals through nuclear transcription factors in the brain. | 2001 Apr |
|
| Atypical neural messengers. | 2001 Feb |
|
| Glutamate receptor dysregulation in the hippocampus of transgenic mice carrying mutated human amyloid precursor protein. | 2001 Feb |
|
| Selective blockade of the mGluR1 receptor reduces traumatic neuronal injury in vitro and improvesoOutcome after brain trauma. | 2001 Feb |
|
| Changes in agonist concentration dependence that are a function of duration of exposure suggest N-methyl-D-aspartate receptor nonsaturation during synaptic stimulation. | 2001 Feb |
|
| Glutamate 2000: old dog, new tricks. | 2001 Feb |
|
| Pharmacological properties of the potent epileptogenic amino acid dysiherbaine, a novel glutamate receptor agonist isolated from the marine sponge Dysidea herbacea. | 2001 Feb |
|
| Effect of adrenalectomy on membrane properties and synaptic potentials in rat dentate granule cells. | 2001 Feb |
|
| Mu opiates inhibit long-term potentiation induction in the spinal cord slice. | 2001 Feb |
|
| Orphenadrine prevents 3-nitropropionic acid-induced neurotoxicity in vitro and in vivo. | 2001 Feb |
|
| Large-dose oral dextromethorphan as an adjunct to patient-controlled analgesia with morphine after knee surgery. | 2001 Feb |
|
| Xenon inhibits but N(2)O enhances ketamine-induced c-Fos expression in the rat posterior cingulate and retrosplenial cortices. | 2001 Feb |
|
| 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 Feb 15 |
|
| Use-dependent effects of amyloidogenic fragments of (beta)-amyloid precursor protein on synaptic plasticity in rat hippocampus in vivo. | 2001 Feb 15 |
|
| Assembly with the NR1 subunit is required for surface expression of NR3A-containing NMDA receptors. | 2001 Feb 15 |
|
| Laminar organization of the NMDA receptor complex within the postsynaptic density. | 2001 Feb 15 |
|
| N-methyl-D-aspartate receptor antagonist reduces nitrotyrosine formation in caudate-putamen in rat focal cerebral ischemia-reperfusion. | 2001 Feb 16 |
|
| Oxytocin enhances presynaptic and postsynaptic glutamatergic transmission between rat olfactory bulb neurones in culture. | 2001 Feb 16 |
|
| Endogenous indoles as novel polyamine site ligands at the N-methyl-D-aspartate receptor complex. | 2001 Feb 2 |
|
| Potassium chloride depolarization mediates CREB phosphorylation in striatal neurons in an NMDA receptor-dependent manner. | 2001 Feb 2 |
|
| Differential gene expression profiling in human brain tumors. | 2001 Feb 7 |
|
| 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 Feb 9 |
|
| Effect of graded hypoxia on the high-affinity CPP binding site of the NMDA receptor in the cerebral cortex of newborn piglets. | 2001 Feb 9 |
|
| 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 Jan |
|
| Old spines can't dance. | 2001 Jan |
|
| The role of group I and group II metabotropic glutamate receptors in modulation of striatal NMDA and quinolinic acid toxicity. | 2001 Jan |
|
| Reduced perisomatic inhibition, increased excitatory transmission, and impaired long-term potentiation in mice deficient for the extracellular matrix glycoprotein tenascin-R. | 2001 Jan |
|
| Mutant huntingtin enhances excitotoxic cell death. | 2001 Jan |
|
| Modeling of evoked field potentials in hippocampal CA1 area describes their dependence on NMDA and GABA receptors. | 2001 Jan 15 |
|
| Mitogen-activated protein kinase/extracellular signal-regulated kinase activation in somatodendritic compartments: roles of action potentials, frequency, and mode of calcium entry. | 2001 Jan 15 |
|
| Hyperfunction of dopaminergic and serotonergic neuronal systems in mice lacking the NMDA receptor epsilon1 subunit. | 2001 Jan 15 |
|
| Cytosolic calcium oscillations in astrocytes may regulate exocytotic release of glutamate. | 2001 Jan 15 |
|
| Quantitative relationship between transmitter release and calcium current at the calyx of held synapse. | 2001 Jan 15 |
|
| Three pairs of cysteine residues mediate both redox and zn2+ modulation of the nmda receptor. | 2001 Jan 15 |
|
| NMDA receptor antagonist AP5 and nitric oxide synthase inhibitor 7-NI affect different phases of learning and memory in goldfish. | 2001 Jan 19 |
|
| Magnesium deprivation decreases cellular reduced glutathione and causes oxidative neuronal death in murine cortical cultures. | 2001 Jan 26 |
|
| A murine model of opioid-induced hyperalgesia. | 2001 Jan 31 |
|
| Intraischemic but not postischemic hypothermia prevents non-selective hippocampal downregulation of AMPA and NMDA receptor gene expression after global ischemia. | 2001 Jan 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 Jan 31 |
|
| Deficits in the expression of the NR2B subunit in the hippocampus of aged Fisher 344 rats. | 2001 Jan-Feb |
|
| Effects of pharmacologically induced changes in NMDA-receptor activity on long-term memory in humans. | 2001 Jan-Feb |
|
| Glycine reduces novelty- and methamphetamine-induced locomotor activity in neonatal ventral hippocampal damaged rats. | 2001 Mar |
|
| Differential and region-specific activation of mitogen-activated protein kinases following chronic administration of phencyclidine in rat brain. | 2001 Mar |
|
| Metabotropic and NMDA glutamate receptors participate in the cannabinoid-induced antinociception. | 2001 Mar |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:01:39 UTC 2023
by
admin
on
Sat Dec 16 10:01:39 UTC 2023
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| Record UNII |
1903B9Q6PI
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| Record Status |
Validated (UNII)
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| Record Version |
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1787 (Number of products:10)
Created by
admin on Sat Dec 16 10:01:39 UTC 2023 , Edited by admin on Sat Dec 16 10:01:39 UTC 2023
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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N-Methyl-D-aspartic acid
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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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admin on Sat Dec 16 10:01:39 UTC 2023 , Edited by admin on Sat Dec 16 10:01:39 UTC 2023
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