All Photos(4)

M3262

Sigma-Aldrich

N-Methyl-D-aspartic acid

≥98% (TLC), solid

Synonym(s):
NMDA, (R)-2-(Methylamino)succinic acid
Empirical Formula (Hill Notation):
C5H9NO4
CAS Number:
Molecular Weight:
147.13
Beilstein:
1724431
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥98% (TLC)

form

solid

application(s)

cell analysis: suitable
cell culture | mammalian: suitable

color

white

mp

189-190 °C

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

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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.

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.

Packaging

1, 5 g in poly bottle
25, 100, 250 mg in poly bottle

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. It acts as a specific agonist for NMDA type glutamate receptors.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
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)
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...
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...

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