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M3262

Sigma-Aldrich

N-Methyl-D-aspartic acid

≥98% (TLC), suitable for cell culture

Synonym(s):

(R)-2-(Methylamino)succinic acid, NMDA

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25 MG
$68.10
100 MG
$151.36
250 MG
$308.00
1 G
$941.60

About This Item

Empirical Formula (Hill Notation):
C5H9NO4
CAS Number:
6384-92-5
Molecular Weight:
147.13
Beilstein/REAXYS Number:
1724431
MDL number:
MFCD00004226
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24277987
NACRES:
NA.32

$68.10

In StockDetails

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Product Name

N-Methyl-D-aspartic acid, ≥98% (TLC), solid

Quality Level

200

assay

≥98% (TLC)

form

solid

technique(s)

cell culture | mammalian: suitable

color

white

mp

189-190 °C

application(s)

cell analysis

SMILES string

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

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

InChI key

HOKKHZGPKSLGJE-GSVOUGTGSA-N

Gene Information

human ... GRIN1(2902) , GRIN2A(2903) , GRIN2B(2904) , GRIN2C(2905) , GRIN2D(2906) , GRINA(2907)
rat ... Gria1(50592) , Grik1(29559) , Grin2a(24409)

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General description

N-Methyl-D-aspartic acid (NMDA) is an endogenously generated molecule in rat nervous system and endocrine glands. NMDA is present at low level (nmol/g) in the adenohypophysis, hypothalamus, brain, and testis. NMDA is derived from D-Asp by an S-adenosylmethionine-dependent enzyme also referred to as NMDA synthase.[1]

Application

N-Methyl-D-aspartic acid has been used to induce N-methyl-d-aspartic acid (NMDA) toxicity, cultures of retinal cells were supplemented with NMDA.[2][3]

Biochem/physiol Actions

Excitotoxic amino acid. Prototypic agonist at the NMDA-type glutamate receptor that regulates ion channels; important in long-term potentiation, ischemia, and epilepsy.
N-Methyl-D-aspartic acid (NMDA) plays a crucial role in release of luteinizing hormone and PRL (prolactin) in the pituitary gland and GnRH (gonadotropin releasing hormone) in the hypothalamus.[1][4] It acts as a specific agonist for NMDA type glutamate receptors.[4]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000417805
0000417805
0000399948
0000395917
0000368193

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Calpain- and caspase-mediated aII-spectrin
and tau proteolysis in rat cerebrocortical
neuronal cultures after ecstasy or
methamphetamine exposure.
Warren MW
The International Journal of Neuropsychopharmacology, 9, 1-11 (2006)
Guendalina Olivero et al.
Molecular neurobiology, 56(9), 6142-6155 (2019-02-09)
Mouse hippocampal glutamatergic nerve endings express presynaptic release-regulating NMDA autoreceptors (NMDARs). The presence of GluN1, GluN2A, GluN2B, and GluN3A subunits in hippocampal vesicular glutamate transporter type 1-positive synaptosomes was confirmed with confocal microscopy. GluN2C, GluN2D, and GluN3B immunopositivity was scarcely
Juan Ding et al.
Neural regeneration research, 14(12), 2112-2117 (2019-08-10)
N-methyl-D-aspartate receptor hypofunction is the basis of pathophysiology in schizophrenia. Blocking the N-methyl-D-aspartate receptor impairs learning and memory abilities and induces pathological changes in the brain. Previous studies have paid little attention to the role of the N-methyl-D-aspartate receptor subunit
Occurrence of D-aspartic acid and N-methyl-D-aspartic acid in rat neuroendocrine tissues and their role in the modulation of luteinizing hormone and growth hormone release.
D'Aniello A
Faseb Journal, 14(5), 699-714 (2000)
N-methyl-D-aspartic acid (NMDA) in the nervous system of the amphioxus Branchiostoma lanceolatum.
D'Aniello S
BMC Neuroscience, 8:109 (2007)
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