N-Methyl-D-aspartic acid

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.

"NMDA" redirects here. For National Minimum Drinking Age, see National Minimum Drinking Age Act.
Not to be confused with MDMA or N-Nitrosodimethylamine.
N-Methyl-D-aspartic acid
Names
IUPAC name
N-Methyl-D-aspartic acid
Systematic IUPAC name
(2R)-2-(Methylamino)butanedioic acid
Other names
N-Methylaspartate; N-Methyl-D-aspartate; NMDA
Identifiers
3D model (JSmol)
1724431
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH N-Methylaspartate
RTECS number
  • CI9457000
UNII
  • 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
  • CN[C@H](CC(=O)O)C(=O)O
Properties
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):
137 mg kg−1 (intraperitoneal, mouse)
Related compounds
Related amino acid derivatives
Related compounds
 Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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