N-Methyl-DL-alanine - 600-21-5

N-Methyl-DL-alanine

Catalog Number: EVT-248113
CAS Number: 600-21-5
Molecular Formula: C7H9N3O2
Molecular Weight: 103.12 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
N-Methyl-DL-alanine (NMDLA) is a non-proteinogenic amino acid that has gained significant attention in recent years due to its potential therapeutic and toxic effects. It is a structural analog of the neurotransmitter glutamate and has been found in various natural sources, including cyanobacteria, diatoms, and shellfish.
Applications in Various Fields
N-Methyl-DL-alanine has various applications in medical research, including its role in drug development, clinical trials, and findings. It has been found to have potential therapeutic effects in the treatment of neurodegenerative diseases, such as Alzheimer's and Parkinson's. However, it also has potential side effects, such as neurotoxicity and the development of neurodegenerative diseases. In environmental research, N-Methyl-DL-alanine has been found to have effects on ecosystems, such as its role in pollution management and sustainability and environmental impact. In industrial research, N-Methyl-DL-alanine has been used in manufacturing processes to improve product quality and efficiency, with health and safety considerations.

Properties

CAS Number

600-21-5

Product Name

N-Methyl-DL-alanine

IUPAC Name

2-(methylamino)propanoic acid

Molecular Formula

C7H9N3O2

Molecular Weight

103.12 g/mol

InChI

InChI=1S/C4H9NO2/c1-3(5-2)4(6)7/h3,5H,1-2H3,(H,6,7)

InChI Key

YCFJXOFFQLPCHD-YFKPBYRVSA-N

SMILES

CC(C(=O)O)NC

Synonyms

Spinacine;59981-63-4;L-4,5,6,7-TETRAHYDRO-1H-IMIDAZO[4,5-C]PYRIDINE-6-CARBOXYLICACID;(6s)-4,5,6,7-tetrahydro-3h-imidazo[4,5-c]pyridine-6-carboxylicacid;AC1L4S5D;UNII-EG040ZE63K;EG040ZE63K;SCHEMBL3739922;SCHEMBL10544160;STOCK1N-50928;CTK1G9647;MolPort-002-524-999;MolPort-028-914-188;KST-1A7279;KST-1A7280;ZINC6090913;7292AH;AR-1A6977;AR-1A6978;KM0361;AKOS006279535;AKOS016370682;MCULE-3762251751;HE035924;HE358403

Canonical SMILES

C1C([NH2+]CC2=C1N=CN2)C(=O)[O-]

Isomeric SMILES

C1[C@H]([NH2+]CC2=C1N=CN2)C(=O)[O-]
Method of Synthesis or Extraction
N-Methyl-DL-alanine can be synthesized using various methods, including the Strecker synthesis, the Gabriel synthesis, and the Mannich reaction. The Strecker synthesis involves the reaction of an aldehyde or ketone with ammonia and hydrogen cyanide, followed by hydrolysis to yield N-Methyl-DL-alanine. The Gabriel synthesis involves the reaction of phthalimide with potassium hydroxide, followed by the addition of methyl iodide and hydrolysis to yield N-Methyl-DL-alanine. The Mannich reaction involves the reaction of formaldehyde, glycine, and methylamine to yield N-Methyl-DL-alanine. The efficiency and yield of each method vary, with the Strecker synthesis being the most efficient and yielding the highest amount of N-Methyl-DL-alanine. However, all methods have environmental and safety considerations, as they involve the use of toxic chemicals and require careful handling.
Chemical Structure and Biological Activity
N-Methyl-DL-alanine has a chemical structure similar to that of glutamate, with a methyl group attached to the alpha-carbon. It acts as an agonist of the N-methyl-D-aspartate (NMDA) receptor, which is involved in synaptic plasticity and memory formation. N-Methyl-DL-alanine has been found to have neurotoxic effects, leading to the development of neurodegenerative diseases such as Alzheimer's and Parkinson's. However, it also has potential therapeutic effects, such as its ability to enhance cognitive function and memory.
Biological Effects
N-Methyl-DL-alanine has been found to affect cell function and signal transduction, leading to changes in synaptic plasticity and memory formation. It has also been found to have potential therapeutic and toxic effects, depending on the dose and duration of exposure. In low doses, N-Methyl-DL-alanine has been found to enhance cognitive function and memory, while in high doses, it can lead to neurotoxicity and the development of neurodegenerative diseases.
Future Perspectives and Challenges
The use and study of N-Methyl-DL-alanine are currently limited by its potential toxic effects and the lack of understanding of its mechanism of action. Possible solutions and improvements include the development of more efficient and safer methods of synthesis or extraction, as well as the identification of its biological targets and mechanisms of action. Future trends and prospects in the application of N-Methyl-DL-alanine in scientific research include its potential use in the treatment of neurodegenerative diseases and its role in improving product quality and efficiency in industrial processes.
Conclusion:
In conclusion, N-Methyl-DL-alanine is a non-proteinogenic amino acid that has gained significant attention in recent years due to its potential therapeutic and toxic effects. It has various applications in medical, environmental, and industrial research, with future trends and prospects in the development of more efficient and safer methods of synthesis or extraction and the identification of its biological targets and mechanisms of action. However, its use and study are currently limited by its potential toxic effects and the lack of understanding of its mechanism of action.

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