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Record Information
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:51 UTC
Update Date2020-05-04 15:40:48 UTC
Secondary Accession Numbers
  • HMDB02393
Metabolite Identification
Common NameN-Methyl-D-aspartic acid
DescriptionN-Methyl-D-aspartic acid is an amino acid derivative acting as a specific agonist at the NMDA receptor, and therefore mimics the action of the neurotransmitter glutamate on that receptor. In contrast to glutamate, NMDA binds to and regulates the above receptor only, but not other glutamate receptors. NMDA is a water-soluble endogenous metabolite that plays an important role in the neuroendocrine system of species across Animalia (PMID: 18096065 ). It was first synthesized in the 1960s (PMID: 14056452 ). NMDA is an excitotoxin; this trait has applications in behavioural neuroscience research. The body of work utilizing this technique falls under the term "lesion studies." Researchers apply NMDA to specific regions of an (animal) subject's brain or spinal cord and subsequently test for the behaviour of interest, such as operant behaviour. If the behaviour is compromised, it suggests that the destroyed tissue was part of a brain region that made an important contribution to the normal expression of that behaviour. Examples of antagonists of the NMDA receptor are ketamine, amantadine, dextromethorphan (DXM), riluzole, and memantine. They are commonly referred to as NMDA receptor antagonists (PMID: 28877137 ).
(R)-2-Methylamino-succinic acidChEBI
2-Methylamino-succinic acidChEBI
Methyl aspartic acidChEBI
N-Methyl aspartic acidChEBI
Methyl aspartateGenerator
N-Methyl aspartateGenerator
N-Methylaspartic acidGenerator
N-Methyl D-aspartateHMDB
N-Methyl D-aspartic acidHMDB
N Methyl D aspartateHMDB
N Methyl D aspartic acidHMDB
Acid, N-methyl-D-asparticHMDB
N MethylaspartateHMDB
Chemical FormulaC5H9NO4
Average Molecular Weight147.1293
Monoisotopic Molecular Weight147.053157781
IUPAC Name(2R)-2-(methylamino)butanedioic acid
Traditional NameN methyl D aspartate
CAS Registry Number6384-92-5
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAspartic acid and derivatives
Alternative Parents
  • Aspartic acid or derivatives
  • Alpha-amino acid
  • D-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Secondary amine
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

Biological location:

Physical Properties
Experimental Properties
Melting Point187 - 192 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility40.6 g/LALOGPS
pKa (Strongest Acidic)1.46ChemAxon
pKa (Strongest Basic)10.34ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.31 m³·mol⁻¹ChemAxon
Polarizability13.18 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k96-9300000000-416b6ee56e62fb8e5961Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9410000000-4a49e66d4a20edeb3235Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9600000000-7a4c870f26f91384c5d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000f-9000000000-5a5c118fa9bc800c8c72Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b494ed61acdeddeb3be4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-eeb3a907ee733c1543e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f80-9600000000-1c3def640e73db97c7e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-9f7de36da4128db64ccbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0900000000-6c4446f90caead6f5b51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufs-3900000000-44106308c45837087fe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ac3-9100000000-fe891bbc2ab7063b8bacSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Brain
  • Fibroblasts
  • Kidney
  • Neuron
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022992
KNApSAcK IDNot Available
Chemspider ID21436
KEGG Compound IDC12269
BioCyc IDCPD-10705
BiGG IDNot Available
Wikipedia LinkN-Methyl-D-aspartic_acid
PubChem Compound22880
PDB IDNot Available
ChEBI ID31882
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hitchcock IS, Skerry TM, Howard MR, Genever PG: NMDA receptor-mediated regulation of human megakaryocytopoiesis. Blood. 2003 Aug 15;102(4):1254-9. Epub 2003 Mar 20. [PubMed:12649130 ]
  2. Miller RF: D-Serine as a glial modulator of nerve cells. Glia. 2004 Aug 15;47(3):275-83. [PubMed:15252817 ]
  3. Sanelli TR, Sopper MM, Strong MJ: Sequestration of nNOS in neurofilamentous aggregate bearing neurons in vitro leads to enhanced NMDA-mediated calcium influx. Brain Res. 2004 Apr 9;1004(1-2):8-17. [PubMed:15033415 ]
  4. Weyermann J, Lochmann D, Georgens C, Zimmer A: Albumin-protamine-oligonucleotide-nanoparticles as a new antisense delivery system. Part 2: cellular uptake and effect. Eur J Pharm Biopharm. 2005 Apr;59(3):431-8. [PubMed:15760723 ]
  5. Baskys A, Blaabjerg M: Understanding regulation of nerve cell death by mGluRs as a method for development of successful neuroprotective strategies. J Neurol Sci. 2005 Mar 15;229-230:201-9. Epub 2004 Dec 15. [PubMed:15760640 ]
  6. Hardingham GE, Bading H: The Yin and Yang of NMDA receptor signalling. Trends Neurosci. 2003 Feb;26(2):81-9. [PubMed:12536131 ]
  7. Lareo LR, Corredor C: Ionotropic glutamate receptor activated by N-methyl-D-aspartate: a key molecule of conscious life. Med Hypotheses. 2004;63(2):245-9. [PubMed:15236783 ]
  8. Fonnum F, Lock EA: The contributions of excitotoxicity, glutathione depletion and DNA repair in chemically induced injury to neurones: exemplified with toxic effects on cerebellar granule cells. J Neurochem. 2004 Feb;88(3):513-31. [PubMed:14720201 ]
  9. Wang GS, Hong CJ, Yen TY, Huang HY, Ou Y, Huang TN, Jung WG, Kuo TY, Sheng M, Wang TF, Hsueh YP: Transcriptional modification by a CASK-interacting nucleosome assembly protein. Neuron. 2004 Apr 8;42(1):113-28. [PubMed:15066269 ]
  10. Liu D, Cheng T, Guo H, Fernandez JA, Griffin JH, Song X, Zlokovic BV: Tissue plasminogen activator neurovascular toxicity is controlled by activated protein C. Nat Med. 2004 Dec;10(12):1379-83. Epub 2004 Oct 31. [PubMed:15516929 ]
  11. Eugenin EA, D'Aversa TG, Lopez L, Calderon TM, Berman JW: MCP-1 (CCL2) protects human neurons and astrocytes from NMDA or HIV-tat-induced apoptosis. J Neurochem. 2003 Jun;85(5):1299-311. [PubMed:12753088 ]
  12. Baskys A, Fang L, Bayazitov I: Activation of neuroprotective pathways by metabotropic group I glutamate receptors: a potential target for drug discovery? Ann N Y Acad Sci. 2005 Aug;1053:55-73. [PubMed:16179509 ]
  13. Okuda H, Ogita K: [Protective effects of N-methyl-D-aspartate against neuronal damages]. Nihon Shinkei Seishin Yakurigaku Zasshi. 2002 Oct;22(5):153-8. [PubMed:12451685 ]
  14. Andre VM, Flores-Hernandez J, Cepeda C, Starling AJ, Nguyen S, Lobo MK, Vinters HV, Levine MS, Mathern GW: NMDA receptor alterations in neurons from pediatric cortical dysplasia tissue. Cereb Cortex. 2004 Jun;14(6):634-46. Epub 2004 Mar 28. [PubMed:15054078 ]
  15. Reyes O, Sosa I, Kuffler DP: Neuroprotection of adult human neurons against ischemia by hypothermia and alkalinization. P R Health Sci J. 2006 Mar;25(1):43-50. [PubMed:16883678 ]
  16. Boehning D, Snyder SH: Novel neural modulators. Annu Rev Neurosci. 2003;26:105-31. [PubMed:14527267 ]
  17. Tuneva EO, Bychkova ON, Boldyrev AA: Effect of NMDA on production of reactive oxygen species by human lymphocytes. Bull Exp Biol Med. 2003 Aug;136(2):159-61. [PubMed:14631498 ]
  18. D'Aniello S, Fisher GH, Topo E, Ferrandino G, Garcia-Fernandez J, D'Aniello A: N-methyl-D-aspartic acid (NMDA) in the nervous system of the amphioxus Branchiostoma lanceolatum. BMC Neurosci. 2007 Dec 20;8:109. doi: 10.1186/1471-2202-8-109. [PubMed:18096065 ]
  19. WATKINS JC: THE SYNTHESIS OF SOME ACIDIC AMINO ACIDS POSSESSING NEUROPHARMACOLOGICAL ACTIVITY. J Med Pharm Chem. 1962 Nov;91:1187-99. doi: 10.1021/jm01241a010. [PubMed:14056452 ]
  20. Aiyer R, Mehta N, Gungor S, Gulati A: A Systematic Review of NMDA Receptor Antagonists for Treatment of Neuropathic Pain in Clinical Practice. Clin J Pain. 2018 May;34(5):450-467. doi: 10.1097/AJP.0000000000000547. [PubMed:28877137 ]


General function:
Cell cycle control, cell division, chromosome partitioning
Specific function:
Binds to type II regulatory subunits of protein kinase A. Scaffolding protein that assembles several protein kinases and phosphatases on the centrosome and Golgi apparatus. May be required to maintain the integrity of the Golgi apparatus. Isoform 4 is associated with the N-methyl-D-aspartate receptor and is specifically found in the neuromuscular junction (NMJ) as well as in neuronal synapses, suggesting a role in the organization of postsynaptic specializations
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in protein binding
Specific function:
GTPase-activating protein (GAP) promoting GTP hydrolysis on RHOA, CDC42 and RAC1 small GTPases. May be involved in the differentiation of neuronal cells during the formation of neurite extensions. Involved in NMDA receptor activity-dependent actin reorganization in dendritic spines. May mediate cross-talks between Ras- and Rho-regulated signaling pathways in cell growth regulation. Isoform 2 has higher GAP activity
Gene Name:
Uniprot ID:
Molecular weight: