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

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

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 
• 1256936-18-1 grassypeptolide C 
• 1010433-25-6 grassypeptolide A 
• 89464-62-0 (+/-)-N-Formyl-N-methyl-asparaginsaeure 
• 144300-47-0 N-methylaspartic acid dimethyl ester 
• 17833-53-3 N-methyl-DL-aspartic acid 

Relevant articles and documents

Preparation method of nitrogen-substituted aspartic acid

The invention discloses a preparation method of nitrogen-substituted aspartic acid, the method comprises the following steps: providing a nitrogen-substituted aspartic acid compound with the structural formula as shown in the specification, wherein R1 is alkyl, and R2 is an amino protecting group; performing deprotection treatment on the nitrogen-substituted aspartic acid compound to obtain the nitrogen-substituted aspartic acid with the structural formula as shown in the specification, and the preparation method disclosed by the invention can be used for reducing the cost of preparing the nitrogen-substituted aspartic acid and enabling the nitrogen-substituted aspartic acid to be suitable for industrial production.

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)

Grassypeptolides A-C, cytotoxic bis-thiazoline containing marine cyclodepsipeptides

Grassypeptolides A-C (1-3), a group of closely related bis-thiazoline containing cyclic depsipeptides, have been isolated from extracts of the marine cyanobacterium Lyngbya confervoides. Although structural differences between the analogues are minimal, comparison of the in vitro cytotoxicity of the series revealed a structure-activity relationship. When the ethyl substituent of 1 is changed to a methyl substituent in 2, activity is only slightly reduced (3-4-fold), whereas inversion of the Phe unit flanking the bis-thiazoline moiety results in 16-23-fold greater potency. We show that both 1 and 3 cause G1 phase cell cycle arrest at lower concentrations, followed at higher concentrations by G2/M phase arrest, and that these compounds bind Cu2+ and Zn 2+. The three-dimensional structure of 2 was determined by MS, NMR, and X-ray crystallography, and the structure of 3 was established by MS, NMR, and chemical degradation. The structure of 3 was explored by in silico molecular modeling, revealing subtle differences in overall conformation between 1 and 3. Attempts to interconvert 1 and 3 with base were unsuccessful, but enzymatic conversion may be possible and could be a novel form of activation for chemical defense.