N-Methyl-D-aspartic acid

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N-Methyl-D-aspartic acid

Names
IUPAC name N-Methyl-D-aspartic acid
Systematic IUPAC name (2R)-2-(Methylamino)butanedioic acid[1]
Other names N-Methylaspartate; N-Methyl-D-aspartate; NMDA
Identifiers
CAS Number	6384-92-5 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1724431
ChEBI	CHEBI:31882 Y
ChEMBL	ChEMBL291278 Y
ChemSpider	21436 Y
IUPHAR/BPS	4268
KEGG	C12269 Y
MeSH	N-Methylaspartate
PubChem CID	22880
RTECS number	CI9457000
UNII	1903B9Q6PI Y
CompTox Dashboard (EPA)	DTXSID8041082
InChI InChI=1 S/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)/t3-/m1/s1 Key: HOKKHZGPKSLGJE-GSVOUGTGSA-N
SMILES CN[C@H](CC(=O)O)C(=O)O
Properties
Chemical formula	C5H9NO4
Molar mass	147.130 g·mol−1
Appearance	White, opaque crystals
Odor	Odorless
Melting point	189 to 190 °C (372 to 374 °F; 462 to 463 K)
log P	1.39
Acidity (pKa)	2.206
Basicity (pKb)	11.791
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	137 mg kg−1 (intraperitoneal, mouse)
Related compounds
Related amino acid derivatives	Sarcosine Dimethylglycine beta-Methylamine-L-alanine
Related compounds	Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

N-methyl-D-aspartic acid or N-methyl-D-aspartate (NMDA) is an amino acid derivative that acts as a specific agonist at the NMDA receptor mimicking the action of glutamate, the neurotransmitter which normally acts at 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, for example, withdrawal from alcohol as this causes symptoms such as agitation and, sometimes, epileptiform seizures.^{[citation needed]}