N-β-Methyl-β-alanine hydrochloride
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N-β-Methyl-β-alanine hydrochloride

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Category
β−Amino Acids
Catalog number
BAT-004785
CAS number
65845-56-9
Molecular Formula
C4H10ClNO2
Molecular Weight
139.58
N-β-Methyl-β-alanine hydrochloride
IUPAC Name
3-(methylamino)propanoic acid;hydrochloride
Synonyms
H-β-MeAla-OH HCl; H-MeGly-(C#CH2)OH HCl; 3-(Methylamino)propanoic acid hydrochloride
Storage
Store at 2-8°C (under N2)
InChI
InChI=1S/C4H9NO2.ClH/c1-5-3-2-4(6)7;/h5H,2-3H2,1H3,(H,6,7);1H
InChI Key
NMVZBHCSFYRWFC-UHFFFAOYSA-N
Canonical SMILES
CNCCC(=O)O.Cl

N-β-Methyl-β-alanine hydrochloride, a versatile compound, finds valuable applications in the pharmaceutical industry. As a key intermediate in the synthesis of various drugs, it contributes significantly to the development of medications targeting neurological disorders and metabolic diseases. Its structural characteristics enable it to effectively participate in the formulation of active pharmaceutical ingredients (APIs), enhancing the overall efficacy and stability of the final product. The compound's remarkable stability under different physiological conditions ensures its consistent performance, making it an indispensable component in the production of high-quality pharmaceuticals.

Another critical application of N-β-Methyl-β-alanine hydrochloride is in biochemical research, where it serves as a crucial component in studying enzyme mechanisms and protein interactions. Researchers leverage this compound to investigate metabolic pathways and enzymatic processes at a molecular level. Its unique properties facilitate the labeling of substrates and competitive inhibition studies, allowing for a deeper understanding of biochemical reactions. This application is vital for deciphering the intricate details of cellular functions and developing targeted therapeutic interventions for various diseases, including cancer and genetic disorders.

N-β-Methyl-β-alanine hydrochloride also plays a significant role in the field of nutritional supplements, particularly in the synthesis of muscle-building and energy-enhancing products. It acts as a precursor for the biosynthesis of carnosine, a dipeptide that helps buffer acid in muscles, thus enhancing athletic performance and reducing fatigue. The inclusion of this compound in dietary supplements aids in the improvement of muscle endurance and overall physical performance, making it a popular choice among athletes and fitness enthusiasts. Its contribution to enhancing muscle recovery post-exercise further underscores its importance in sports nutrition.

In the realm of agrochemicals, N-β-Methyl-β-alanine hydrochloride is utilized as a building block for the synthesis of various herbicides and plant growth regulators. Its chemical properties enable it to integrate seamlessly into formulations that control weed proliferation and stimulate plant growth under different environmental conditions. The role of this compound in agrochemicals is crucial for ensuring high crop yields and sustainable agricultural practices. By contributing to the development of effective agrochemical solutions, N-β-Methyl-β-alanine hydrochloride supports the agricultural industry's efforts to meet the food demands of a growing global population.

1. Metal-free and regiospecific synthesis of 3-arylindoles
Chuangchuang Xu, Wenlai Xie, Jiaxi Xu Org Biomol Chem. 2020 Apr 8;18(14):2661-2671. doi: 10.1039/d0ob00317d.
A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ring-opening reaction of aryloxiranecarbonitriles and arylhydrazine hydrochlorides and Fischer indolization. The organic base triethylamine plays a crucial role in the final elimination step in the Fischer indole synthesis, affording 3-arylindoles regiospecifically. The reaction features advantages of microwave acceleration, non-metal participation, short reaction time, organic acid-base co-catalysis, and broad substrate scope.
2. 1-Haloacylpiperazines
S Groszkowski, J Sienkiewicz, L Korzycka Pol J Pharmacol Pharm. 1975 Apr-Jun;27(2):183-6.
By direct acylation of piperazine with halogenocarboxylic acid chlorides in acid medium, the hydrochlorides of 1-haloacylpiperazines were obtained.
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