6384-92-5

Basic information

• Product Name: N-Methyl-D-aspartic acid
• Synonyms: n-methylaspartate;n-methyl-d-aspartate;n-methyl-d-asparticaci;H-D-MEASP-OH;H-D-MEASP-OH HCL;[R]-2-[METHYLAMINO]SUCCINIC ACID;N-ALPHA-METHYL-D-ASPARTIC ACID;N-ALPHA-METHYL-D-ASPARTIC ACID HYDROCHLORIDE
• CAS NO: 6384-92-5
• Molecular Formula: C₅H₉NO₄
• Molecular Weight: 147.13
• EINECS: 227-012-0
• Product Categories: Glutamate receptor;Glutamate;amino acids;Inhibitors;Pyridines
• Mol File: 6384-92-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 187-192 °C
• Boiling Point: 267.21°C (rough estimate)
• Flash Point: 109.978 °C
• Appearance: white/solid
• Density: 1.4285 (rough estimate)
• Vapor Pressure: 0.0042mmHg at 25°C
• Refractive Index: -15 ° (C=2, H2O)
• Storage Temp.: Store at RT.
• Solubility: Aqueous Acid (Slightly), DMSO (Slightly), Water (Slightly)
• PKA: 2.21±0.23(Predicted)
• Water Solubility: slightly soluble
• Sensitive: Hygroscopic
• Merck: 14,6662
• BRN: 1724431
• CAS DataBase Reference: N-Methyl-D-aspartic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-D-aspartic acid(6384-92-5)
• EPA Substance Registry System: N-Methyl-D-aspartic acid(6384-92-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: CI9457000
• F: 10
• Hazardous Substances Data: 6384-92-5(Hazardous Substances Data)

Usage

Description

N-Methyl-D-aspartic acid (NMDA) is a specific agonist for the NMDA receptor, which mimics the action of glutamate, the neurotransmitter that typically acts at this receptor. It plays a crucial role in the central nervous system and is involved in various physiological and pathological processes.

Uses

Used in Pharmaceutical Industry:
NMDA is used as a pharmaceutical agent for its agonistic effects on the NMDA receptor. It is utilized in the development of drugs targeting neurological disorders and conditions related to the central nervous system.
Used in Research Applications:
NMDA is used as a research tool in neuroscience to study the function and role of the NMDA receptor in synaptic plasticity, learning, and memory. It aids in understanding the mechanisms underlying various neurological conditions and the development of potential therapeutic agents.
Used in Neuroprotection:
NMDA is used in neuroprotective strategies to prevent or reduce neuronal damage in conditions such as stroke, traumatic brain injury, and neurodegenerative diseases. Its agonistic action on the NMDA receptor can help maintain neuronal function and promote recovery.
Used in Drug Development:
NMDA is used in the development of drugs that target the NMDA receptor for the treatment of various neurological and psychiatric disorders, including Alzheimer's disease, Parkinson's disease, and schizophrenia. Its agonistic properties can contribute to the modulation of neurotransmission and the improvement of cognitive function.

Biological Activity

Prototypic NMDA receptor agonist. Also available as part of the Mixed NMDA Receptor Tocriset? .

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.

references

[1] watkins jc, jane de. the glutamate story. br j pharmacol. 2006 jan;147 suppl 1:s100-8.[2] lafon-cazal m, pietri s, culcasi m, bockaert j. nmda-dependent superoxide production and neurotoxicity. nature. 1993 aug 5;364(6437):535-7.

InChI:InChI=1/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)/p-1/t3-/m1/s1

Synthetic route

(2R,2'R)-N-<3'-(methoxycarbonyl)-2'-(methylamino)propionyl>bornane-10,2-sultam → N-methyl-D-aspartate (6384-92-5)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran at 0℃;	94%

N-methyl-benzyl-aspartic acid → N-methyl-D-aspartate (6384-92-5)

Conditions	Yield
With palladium on activated charcoal; water In methanol at 30 - 50℃; for 0.0833333h; Autoclave;	70.92%

(2R)-aspartic acid (1783-96-6) + dimethyl sulfate (77-78-1) → N-methyl-D-aspartate (6384-92-5)

Conditions	Yield
(i) TsCl, aq. NaOH, (ii) /BRN= 635994/, (iii) Na, liq. NH3; Multistep reaction;

D-(-)-N-Methyl-N-formyl-asparaginsaeure → N-methyl-D-aspartate (6384-92-5)

Conditions	Yield
With dihydrogen peroxide

(2R)-aspartic acid (1783-96-6) + methyl iodide (74-88-4) → N-methyl-D-aspartate (6384-92-5)

Conditions	Yield
With sodium carbonate

(S)-β-(α-Carboxy-2-nitrobenzyl) N-methylaspartic acid trifluoroacetate salt → N-methyl-D-aspartate (6384-92-5) + (2-nitrosophenyl)glyoxalic acid

Conditions	Yield
With phosphate buffer Quantum yield; Ambient temperature; Irradiation; different buffers; pH: 3.5-10.8; rate of decay of intermediate;

(2R,2'R)-N-<2'-<(hydroxy)(methyl)amino>-3'-(methoxycarbonyl)propionyl>bornane-10,2-sultam → N-methyl-D-aspartate (6384-92-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / Zn, 1N HCl/AcOH / 48 h / 0 °C 2: 94 percent / 1N LiOH / tetrahydrofuran / 0 °C View Scheme

N-methyl-DL-aspartic acid (17833-53-3) → N-methyl-D-aspartate (6384-92-5)

Conditions	Yield
Multi-step reaction with 3 steps 3: aq. H2O2 View Scheme

N-methylaspartic acid dimethyl ester (144300-47-0) → N-methyl-D-aspartate (6384-92-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: H2O 4: aq. H2O2 View Scheme

(+/-)-N-Formyl-N-methyl-asparaginsaeure (89464-62-0) → N-methyl-D-aspartate (6384-92-5)

Conditions	Yield
Multi-step reaction with 2 steps 2: aq. H2O2 View Scheme

grassypeptolide A (1010433-25-6) → (R)-2-aminobutyric acid (2623-91-8) + D-allo-threonine (24830-94-2) + N-methyl-L-valine (2480-23-1) + N-methyl-D-aspartate (6384-92-5) + L-Cysteic acid (498-40-8) + D-Cysteic acid (35554-98-4) + N-methyl-L-aspartic acid (4226-18-0) + L-proline (147-85-3)

Conditions	Yield
Stage #1: grassypeptolide A With ozone at 20℃; for 0.5h; Stage #2: oxidative conditions;

...Expand

grassypeptolide C (1256936-18-1) → (R)-2-aminobutyric acid (2623-91-8) + D-allo-threonine (24830-94-2) + N-methyl-L-valine (2480-23-1) + N-methyl-D-aspartate (6384-92-5) + L-Cysteic acid (498-40-8) + D-Cysteic acid (35554-98-4) + N-methyl-L-aspartic acid (4226-18-0) + L-proline (147-85-3)

Conditions	Yield
Stage #1: grassypeptolide C With ozone at 20℃; for 0.5h; Stage #2: oxidative conditions;

...Expand

calcium N-methyl-D-aspartate → N-methyl-D-aspartate (6384-92-5)

Conditions	Yield
With cation exchange resin pH=2; pH-value;	62.2 g

N-hydroxymethyl-D-aspartic acid dimethyl ester → N-methyl-D-aspartate (6384-92-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: palladium on activated charcoal; hydrogen / ethanol / 5 h / 20 °C / Heating 2.1: sodium hydroxide / 8 h / Reflux 2.2: pH 2.5 - 6.5 3.1: cation exchange resin / pH 2 View Scheme

N-methyl-D-aspartate (6384-92-5) + di-tert-butyl dicarbonate (24424-99-5) → (R)-2-(tert-Butoxycarbonyl-methyl-amino)-succinic acid

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water for 72h; Ambient temperature;	77%

propan-1-ol (71-23-8) + N-methyl-D-aspartate (6384-92-5) → D-N-Methyl-asparaginsaeure-di-n-propylester

Conditions	Yield
With hydrogenchloride

formaldehyd (50-00-0) + N-methyl-D-aspartate (6384-92-5) → D-(-)-N,N-Dimethyl-asparaginsaeure

Conditions	Yield
With hydrogen; palladium on activated charcoal

Upstream product

• 1783-96-6 (2R)-aspartic acid 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 17833-53-3 N-methyl-DL-aspartic acid 
• 144300-47-0 N-methylaspartic acid dimethyl ester 
• 89464-62-0 (+/-)-N-Formyl-N-methyl-asparaginsaeure 
• 1010433-25-6 grassypeptolide A 
• 1256936-18-1 grassypeptolide C 

Relevant articles and documents

Caged Bioactive Carboxylates. Synthesis, Photolysis Studies, and Biological Characterization of a New Caged N-Methyl-D-aspartic Acid

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Pig growth urges the medicinal preparation preparation method of gene expression (by machine translation)

The invention discloses a Pig growth gene expression urges the medicinal preparation preparation method, the present invention relates to a synthesis of amino acid derivatives, in particular to a Pig growth gene expression urges the medicinal preparation D - aspartic acid derivatives, N - methyl - D - aspartic acid of preparation method, through D - aspartic acid as the raw material, the D - aspartic acid with methanol and thionyl chloride reaction generating D - aspartic acid dimethyl ester hydrochloride, then with 40% formaldehyde of the woven fabric under the alkaline condition generating N - hydroxymethyl - D - aspartic acid, using pd/c as the catalyst under normal temperature and pressure hydrogenation to obtain N - methyl - D - aspartic acid; simple preparation method of the invention, the prepared product quality is stable, and in the preparation of environmental pollution, can promote the growth of livestock and at the same time, improve the utilization rate of the feed and the improvement of the quality of the carcass raising the Pig, popularization and application. (by machine translation)

Enantioselective synthesis of α-N-alkylamino acids via sultam-directed 'enolate' hydroxyamination

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