N-α-Methyl-L-aspartic acid
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N-α-Methyl-L-aspartic acid

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Category
L-Amino Acids
Catalog number
BAT-002091
CAS number
4226-18-0
Molecular Formula
C5H9NO4
Molecular Weight
147.13
N-α-Methyl-L-aspartic acid
IUPAC Name
(2S)-2-(methylamino)butanedioic acid
Synonyms
(S)-2-(Methylamino)succinic acid; Aspartic acid, N-methyl-L-Aspartic acid, N-methyl- (9CI); H-MeAsp-OH nH2O
Appearance
white to off-white crystalline powder
Purity
95%
Density
1.343 g/cm3
Boiling Point
258.2°C
Storage
Store at RT
InChI
InChI=1S/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)/t3-/m0/s1
InChI Key
HOKKHZGPKSLGJE-VKHMYHEASA-N
Canonical SMILES
CNC(CC(=O)O)C(=O)O

N-α-Methyl-L-aspartic acid, more commonly referred to as N-Methyl-D-aspartic acid (NMDA), is an amino acid derivative that acts as a specific agonist at the NMDA receptor, mimicking the action of the neurotransmitter glutamate. 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. This property makes NMDA particularly important in neurological studies and pharmacology. NMDA receptors play a crucial role in synaptic plasticity, memory function, and neurodevelopment. In particular, they become vital during neuronal overactivity, such as during alcohol withdrawal, where they might contribute to symptoms such as seizures. As an agonist, NMDA enables researchers to study the precise mechanisms of excitatory neurotransmitter release and reception in the brain, providing insights into both physiological and pathological neural processes.

In neuroscience research, NMDA is primarily used in inducing neuronal lesions to study behavioral and physiological changes. Its excitotoxic properties make it useful in experimental models to mimic conditions such as stroke and neurodegenerative diseases, helping scientists understand the mechanics of these conditions. The mechanism involves NMDA binding to NR2 subunits of the receptor, opening a cation channel that allows Ca²⁺ and Na⁺ into the cell while K⁺ exits. This process is crucial for synaptic plasticity and memory function as it increases intracellular calcium levels, acting as a second messenger in various signaling pathways. Thus, NMDA serves as a tool for investigating synaptic transmission and plasticity, key aspects of learning and memory.

NMDA also finds application in the field of neuropharmacology, particularly in the study of NMDA receptor antagonists. Compounds like ketamine, memantine, and dextromethorphan are known to block the NMDA receptor, which may be beneficial in treating conditions such as chronic pain and major depressive disorder. By understanding NMDA receptor activation and antagonism, researchers can develop drugs that modulate the receptor’s activity, offering potential therapies for psychiatric and neurological disorders. Therefore, NMDA helps in characterizing these therapeutic interventions and advancing treatment strategies that target the glutamatergic system.

Furthermore, in the context of neuroendocrinology, NMDA plays an essential role as a neuroendocrine regulator. At homeostatic levels, it is involved in the regulation of hormone secretion, affecting processes such as sexual maturation and stress responses. Researchers use NMDA to explore these physiological processes, focusing on how excitatory amino acids regulate endocrine functions. This involves examining NMDA’s impact on the hypothalamic-pituitary axis and its potential to influence the release of hormones like gonadotropins and corticotropin. Thus, NMDA provides vital insights into the complex interactions between neurotransmitters and endocrine systems.

1. The Stephan Curve revisited
William H Bowen Odontology. 2013 Jan;101(1):2-8. doi: 10.1007/s10266-012-0092-z. Epub 2012 Dec 6.
The Stephan Curve has played a dominant role in caries research over the past several decades. What is so remarkable about the Stephan Curve is the plethora of interactions it illustrates and yet acid production remains the dominant focus. Using sophisticated technology, it is possible to measure pH changes in plaque; however, these observations may carry a false sense of accuracy. Recent observations have shown that there may be multiple pH values within the plaque matrix, thus emphasizing the importance of the milieu within which acid is formed. Although acid production is indeed the immediate proximate cause of tooth dissolution, the influence of alkali production within plaque has received relative scant attention. Excessive reliance on Stephan Curve leads to describing foods as "safe" if they do not lower the pH below the so-called "critical pH" at which point it is postulated enamel dissolves. Acid production is just one of many biological processes that occur within plaque when exposed to sugar. Exploration of methods to enhance alkali production could produce rich research dividends.
2. Acidity characterization of heterogeneous catalysts by solid-state NMR spectroscopy using probe molecules
Anmin Zheng, Shang-Bin Liu, Feng Deng Solid State Nucl Magn Reson. 2013 Oct-Nov;55-56:12-27. doi: 10.1016/j.ssnmr.2013.09.001. Epub 2013 Sep 20.
Characterization of the surface acidic properties of solid acid catalysts is a key issue in heterogeneous catalysis. Important acid features of solid acids, such as their type (Brønsted vs. Lewis acid), distribution and accessibility (internal vs. external sites), concentration (amount), and strength of acid sites are crucial factors dictating their reactivity and selectivity. This short review provides information on different solid-state NMR techniques used for acidity characterization of solid acid catalysts. In particular, different approaches using probe molecules containing a specific nucleus of interest, such as pyridine-d5, 2-(13)C-acetone, trimethylphosphine, and trimethylphosphine oxide, are compared. Incorporation of valuable information (such as the adsorption structure, deprotonation energy, and NMR parameters) from density functional theory (DFT) calculations can yield explicit correlations between the chemical shift of adsorbed probe molecules and the intrinsic acid strength of solid acids. Methods that combine experimental NMR data with DFT calculations can therefore provide both qualitative and quantitative information on acid sites.
3. Atroposelective Synthesis of 1,1'-Bipyrroles Bearing a Chiral N-N Axis: Chiral Phosphoric Acid Catalysis with Lewis Acid Induced Enantiodivergence
Yaru Gao, Luo-Yu Wang, Tao Zhang, Bin-Miao Yang, Yu Zhao Angew Chem Int Ed Engl. 2022 Apr 11;61(16):e202200371. doi: 10.1002/anie.202200371. Epub 2022 Feb 24.
We present herein a highly efficient atroposelective synthesis of axially chiral 1,1'-bipyrroles bearing an N-N linkage from simple hydrazine and 1,4-diones. Further product derivatizations led to axially chiral bifunctional compounds with high potential in asymmetric catalysis. For this chrial phosphoric acid (CPA)-catalyzed double Paal-Knorr reaction, an intriguing Fe(OTf)3 -induced enantiodivergence was also observed.
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