N-METHYL-L-ASPARTIC ACID

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

Structure Search

SMILES

CN[C@@H](CC(O)=O)C(O)=O

InChI

InChIKey=HOKKHZGPKSLGJE-VKHMYHEASA-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-/m0/s1

HIDE SMILES / InChI

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

Approval Year

PubMed

Title	Date	PubMed
In vitro tolerance to inhibition by ethanol of N-methyl-D-aspartate-induced depolarization in locus coeruleus neurons of behaviorally ethanol-tolerant rats.	2001-07	11311449
Beta -amyloid-(1-42) impairs activity-dependent cAMP-response element-binding protein signaling in neurons at concentrations in which cell survival Is not compromised.	2001-05-18	11278679
Interleukin-10 prevents glutamate-mediated cerebellar granule cell death by blocking caspase-3-like activity.	2001-05-01	11312295
Neuroprotection mediated by glial cell line-derived neurotrophic factor: involvement of a reduction of NMDA-induced calcium influx by the mitogen-activated protein kinase pathway.	2001-05-01	11312287
Inverse agonist action of Leu-enkephalin at delta(2)-opioid receptors mediates spinal antianalgesia.	2001-05	11303046
Long-term memory formation in the chick requires mobilization of ryanodine-sensitive intracellular calcium stores.	2001-05	11300735
Glutamate release via NO production evoked by NMDA in the NTS enhances hypotension and bradycardia in vivo.	2001-05	11294745
Blockade of AMPA/kainate receptors can either decrease or increase the survival of cultured neocortical cells depending on the stage of maturation.	2001-05	11248399
Phosphorylation of protein phosphatase inhibitor-1 by Cdk5.	2001-04-27	11278334
Regulation of sensorimotor gating in rats by hippocampal NMDA: anatomical localization.	2001-04-20	11306005
Activation of p44/p42 MAP kinase in striatal neurons via kainate receptors and PI3 kinase.	2001-04-18	11311983
Presynaptic N-methyl-D-aspartate receptor activation inhibits neurotransmitter release through nitric oxide formation in rat hippocampal nerve terminals.	2001-04-18	11311981
BDNF mediates the neuroprotective effect of PACAP-38 on rat cortical neurons.	2001-04-17	11303760
Cell death in the superficial dorsal horn in a model of neuropathic pain.	2001-04-15	11288144
The metabotropic glutamate receptor agonist 1S,3R-ACPD stimulates and modulates NMDA receptor mediated excitotoxicity in organotypic hippocampal slice cultures.	2001-04-13	11292452
Enhanced NMDA receptor activity in retinal inputs to the rat suprachiasmatic nucleus during the subjective night.	2001-04-01	11283234
Protein-coenzyme interactions in adenosylcobalamin-dependent glutamate mutase.	2001-04-01	11256957
Increases in cortical glutamate concentrations in transgenic amyotrophic lateral sclerosis mice are attenuated by creatine supplementation.	2001-04	11299300
NMDA-evoked calcium transients and currents in the suprachiasmatic nucleus: gating by the circadian system.	2001-04	11298803
NMDA-induced phosphorylation of the microtubule-associated protein MAP-2 is mediated by activation of nitric oxide synthase and MAP kinase.	2001-04	11298788
Amphiphilic, tri-block copolymers provide potent membrane-targeted neuroprotection.	2001-04	11292683
Tyrosine phosphorylation of insulin receptor substrate-1 (IRS-1) by oxidant stress in cerebellar granule neurons: modulation by N-methyl-D-aspartate through calcineurin activity.	2001-04	11279262
Thalamocortical NMDA conductances and intracortical inhibition can explain cortical temporal tuning.	2001-04	11276234
Protein kinase C modulates NMDA receptor trafficking and gating.	2001-04	11276228
Voltage-dependent calcium channels in the rat retina: involvement in NMDA-stimulated influx of calcium.	2001-04	11273667
NMDA receptor activation enhances diazepam binding inhibitor and its mRNA expressions in mouse cerebral cortical neurons.	2001-03-31	11295242
Effect of beta-estradiol on voltage-gated Ca(2+) channels in rat hippocampal neurons: a comparison with dehydroepiandrosterone.	2001-03-30	11290370
Biocompatibility of silicon-based arrays of electrodes coupled to organotypic hippocampal brain slice cultures.	2001-03-30	11277967
Expression and regulation of Na pump isoforms in cultured cerebellar granule cells.	2001-03-26	11277591
The effect of N-acetyl-L-aspartic acid dilithium salt on dopamine release and synthesis in the rat striatum in vivo.	2001-03-23	11282114
Characterization of the glutamatergic system for induction and maintenance of allodynia.	2001-03-23	11259776
Interleukin-2 modulates N-methyl-D-aspartate receptors of native mesolimbic neurons.	2001-03-16	11251197
NMDA and glycine regulate the affinity of the Mg2+-block site in NR1-1a/NR2A NMDA receptor channels expressed in Xenopus oocytes.	2001-03-09	11292060
Attenuation of hyperalgesia by LY235959, a competitive N-methyl-D-aspartate receptor antagonist.	2001-03-09	11245826
Balance between four types of synaptic input for the integrate-and-fire model.	2001-03-07	11237570
NMDA-responsible, APV-insensitive receptor in cultured human astrocytes.	2001-03-02	11270622
Regulatory role of nitric oxide over hippocampal 5-HT release in vivo.	2001-03	11284445
Pituitary hormone and insulin responses to infusion of amino acids and N-methyl-D,L-aspartate in horses.	2001-03	11263835
Effects of glutathione depletion by 2-cyclohexen-1-one on excitatory amino acids-induced enhancement of activator protein-1 DNA binding in murine hippocampus.	2001-03	11259509
Increased expression of NR2A subunit does not alter NMDA-evoked responses in cultured fetal trisomy 16 mouse hippocampal neurons.	2001-03	11259484
Dopaminergic substantia nigra neurons express functional nmda receptors in postnatal rats.	2001-03	11248004
Reduction of functional N-methyl-D-aspartate receptors in neurons by RNase P-mediated cleavage of the NR1 mRNA.	2001-03	11238723
Superoxide dismutase activity in organotypic midbrain-striatum co-cultures is associated with resistance of dopaminergic neurons to excitotoxicity.	2001-03	11238718
NMDA recepter-mediated neuroprotection by essential oils from the rhizomes of Acorus gramineus.	2001-02-16	11253173
Effects of iontophoretically applied substance P, calcitonin gene-related peptide on excitability of dorsal horn neurones in rats.	2001-02	11293504
Short-term adaptation in the peripheral auditory system is related to the AMPA receptor.	2001-01	11270489
Altered responsiveness to stress and NMDA following prenatal exposure to cocaine.	2001-01	11239996
Neuronal injury-induced expression and release of apolipoprotein E in mixed neuron/glia co-cultures: nuclear factor kappaB inhibitors reduce basal and lesion-induced secretion of apolipoprotein E.	2001	11311545
Effects of the calcium release inhibitor dantrolene and the Ca2+-ATPase inhibitor thapsigargin on spinal nociception in rats.	2001	11287815
Hyperactivity and disruption of prepulse inhibition induced by N-methyl-D-aspartate stimulation of the ventral hippocampus and the effects of pretreatment with haloperidol and clozapine.	2001	11246148

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:35:20 GMT 2025` Edited by `admin` on `Mon Mar 31 19:35:20 GMT 2025`
Record UNII	06M97TDT18
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-16206

Preferred Name

English

N-METHYL-L-ASPARTIC ACID

Systematic Name

English

L-ASPARTIC ACID, N-METHYL-

Common Name

English

N-METHYL-L-ASPARTATE

Systematic Name

English

ASPARTIC ACID, N-METHYL-, L-

Common Name

English

METHYL ASPARTIC ACID, L-

Systematic Name

English

N-METHYLASPARTIC ACID

Systematic Name

English

Code System Code Type Description

PUBCHEM

92982