15920-93-1

Basic information

• Product Name: 3-(N-Methylamino)-L-alanine
• Synonyms: -Methylamino-L-alanine;(S)-2-Amino-3-(methylamino)propionic acid;(S)-BMAA;3-(Methylamino)-L-alanine;3-Methylamino-L-alanine;L-Alanine, 3-(methylamino)-;L-Bmaa;3-(Methylamino)-L-alaninehydrochloride
• CAS NO: 15920-93-1
• Molecular Formula: C4H10N2O2
• Molecular Weight: 118.13
• Product Categories: Amino Acids & Derivatives;Neurochemicals;Amino Acids
• Mol File: 15920-93-1.mol

Chemical Properties

• Boiling Point: 284.2 °C at 760 mmHg
• Flash Point: 125.7 °C
• Appearance: white/solid
• Density: 1.157 g/cm³
• Vapor Pressure: 0.000783mmHg at 25°C
• Refractive Index: 1.484
• Storage Temp.: −20°C
• Solubility: H2O: solutions may be stored for several days at 4?#x00b0;Csolub
• CAS DataBase Reference: 3-(N-Methylamino)-L-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(N-Methylamino)-L-alanine(15920-93-1)
• EPA Substance Registry System: 3-(N-Methylamino)-L-alanine(15920-93-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 15920-93-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
3-(N-Methylamino)-L-alanine is used as a research compound for studying its role in neurodegenerative disorders. The expression is: 3-(N-Methylamino)-L-alanine is used as a research compound for investigating its potential contribution to neurodegenerative disorders such as Alzheimer's disease, ALS, and ALS-PDC.
Used in Environmental Studies:
3-(N-Methylamino)-L-alanine is used as a biomarker in environmental studies to assess the presence of cyanobacterial toxins in water bodies. The expression is: 3-(N-Methylamino)-L-alanine is used as a biomarker for detecting cyanobacterial toxins in environmental samples, helping to monitor water quality and potential health risks.
Used in Toxicology:
3-(N-Methylamino)-L-alanine is used as a toxicological agent to understand its mechanism of action and potential effects on the nervous system. The expression is: 3-(N-Methylamino)-L-alanine is used as a toxicological agent to study its impact on neuronal function and its role in the development of neurodegenerative diseases.
Used in the Food Industry:
3-(N-Methylamino)-L-alanine is used as a contaminant monitor in the food industry, particularly in products derived from cyanobacteria or those that may be exposed to cyanobacterial toxins. The expression is: 3-(N-Methylamino)-L-alanine is used as a contaminant monitor in the food industry to ensure the safety and quality of products that may be at risk of cyanobacterial toxin contamination.

Biological Activity

Neurotoxic glutamate agonist originally isolated from Cycas circinalis. Implicated in the pathogenesis of amyotrophic lateral sclerosis-Parkinsonism-dementia complex of Guam (Guam ALS-PD).

InChI:InChI=1/C4H10N2O2/c1-6-2-3(5)4(7)8/h3,6H,2,5H2,1H3,(H,7,8)/t3-/m0/s1

Upstream product

• 119945-11-8 DL-3-methylamino-3-acetylamino-propionic acid 
• 147769-96-8 3-methyl-1-[2-(piperidin-1-yl)phenyl]butan-1-imine 
• 110-89-4 piperidine 
• 72752-52-4 2-(piperidin-1-yl)benzonitrile 
• 873-32-5 2-Chlorobenzonitrile 
• 765306-65-8 3-methyl-1-[2-(1-piperidinyl)phenyl]butoxime 
• 219921-93-4 (R)-3-methyl-1-(2-(1-pieridinyl)phenyl)-butylamine 
• 147770-03-4 3-methyl-1-(2-piperidin-1-yl-phenyl)-butan-1-one 
• 446-52-6 2-Fluorobenzaldehyde 
• 765306-66-9 3-methyl-1-(2-fluorophenyl)butan-1-ol 
• 626219-78-1 3-methyl-1-(2-fluorophenyl)butan-1-one 
• 394-47-8 2-fluorobenzonitrile 

Relevant articles and documents

Novel method for preparing repaglinide intermediate

The invention discloses a novel process for preparing a repaglinide intermediate, which takes o-fluorobenzonitrile as an initial raw material and obtains a target product that is repaglinide racematethrough a Grignard reaction, a condensation reaction and a reduction reaction. The novel synthetic process is high in yield, suitable for industrial mass production, economical and environment-friendly, and the target product can be further used for preparing the medicine repaglinide for treating diabetes mellitus through condensation.

Preparation of 3-methyl-1 - [2 - (1-piperidinyl) phenyl] ding Yaan and the method of use of the product of

The invention discloses a method for preparing 3-methyl-1-(2-(1-piperidyl) phenyl) butyl imine and the application of the 3-methyl-1-(2-(1-piperidyl) phenyl) butyl imine. The yield of the 3-methyl-1-(2-(1-piperidyl) phenyl) butyl imine is 30 to 35 percent; the purity of the 3-methyl-1-(2-(1-piperidyl) phenyl) butyl imine is 99.0 to 99.5 percent (detected by an HPLC (high performance liquid chromatography) method); the 3-methyl-1-(2-(1-piperidyl) phenyl) butyl imine can be used as a standard substance for detecting impurities during the preparation of repaglinide amine, and can also be used for preparing high-purity repaglinide amine after subjected to catalytic hydrogenation or preparing 3-methyl-1-(2-(1-piperidyl) butanone after subjected to acidolysis; and the prepared 3-methyl-1-(2-(1-piperidyl) butanone can be used as raw material for synthesizing repaglinide amine or 3-methyl-1-(2-(1-piperidyl) phenyl) butyl imine, so as to be recycled, and raw material waste is avoided. The method is applicable to the synthesis of repaglinide amine.

Process for the enantiomeric enrichment of 3-methyl-1-(2-piperidinophenyl)-1-butylamine

The present invention relates to a process for the enantiomeric enrichment of 3-methyl-1-(2-piperidinophenyl)-1-butylamine (hereinafter PPA), the process comprising the fractional crystallization of PPA in the form of its acid-addition salt with an achiral carboxylic acid of the formula A, in particular a carboxylic acid of the formula A' as described herein from a solution or emulsion containing a mixture of the enantiomers of PPA and the achiral carboxylic acid of the formula A, preferably in the presence of seed crystals of the acid addition salt of the desired enantiomer of PPA with the achiral carboxylic acid of the formula A, whereby the acid-addition salt of PPA with the achiral carboxylic acid of the formula A is obtained, which is enantiomerically enriched with regard to the desired enantiomer of PPA. wherein n is 0 or 1, k is 0 or 1 and wherein R is C1-C4-alkyl, C1-C4-alkoxy and halogen, in particular methyl, methoxy or chlorine.

Process for the preparation of substantially optically pure Repaglinide and precursors thereof

The invention relates to a process for preparing substantially optically pure Repaglinide and pharmaceutically acceptable salts, solvates and esters thereof, as well as precursors therefore.

An improved process for repaglinide via an efficient and one pot process of (1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine - A useful intermediate

The development of a large-scale synthesis for (1S)-3-methyl-1-(2- piperidin-1-ylphenyl)butan-1-amine (S-(+)-1), a key intermediate of repaglinide (2), is described. The process conditions for S-(+)-1 involving nucleophilic substitution, Grignard reaction, reduction and resolution were optimized and telescoped. The racemization of the undesired enantiomer R-(-)-1 offers a distinctive advantage in terms of cost and overall yield over the existing process. This communication also describes the control of a DCU byproduct obtained during the condensation of S-(+)-1 with phenyl acetic acid derivative 3 in the synthesis of 2. Schweizerische Chemische Gesellschaft.

Substituted compounds derived from N-(benzyl)phenylacetamide, preparation and uses

This invention relates to poly-substituted derivatives of the N-(benzyl)phenylacetamide type, pharmaceutical compositions comprising same, therapeutic uses thereof, more particularly in the fields of human and animal health. This invention also relates to a process for the preparation of such derivatives.

Process for preparing (RS) 3-methyl-1-(2-piperidinyl phenyl) butyl amine

The Present invention relates to a process for the preparation of (RS) 3-methyl-1-(2-piperidinyl phenyl) butyl amine of formula 1. (RS) 3-Methyl-1-(2-piperidinyl phenyl butyl amine having formula 1 is an important key intermediate for the synthesis of repaglinide of formula 2 an oral hypoglycemic agent.

Repaglinide and related hypoglycemic benzoic acid derivatives

The structure-activity relationships in two series of hypoglycemic benzoic acid derivatives (5, 6) were investigated. Series 5 resulted from meglitinide (3) when the 2-methoxy was replaced by an alkyleneimino residue. Maximum activity was observed with the cis-3,5-dimethylpiperidino (5h) and the octamethyleneimino (5l) residues. Series 6 resulted from the meglitinide analogon 4 bearing an inversed amido function when the 2-methoxy, the 5- fluoro, and the α-methyl residue were replaced by a 2-piperidino, a 5- hydrogen, and a larger α-alkyl residue, respectively. An alkoxy residue ortho to the carboxy group further increased activity and duration of action in the rat. The most active racemic compound, 6al (R4 = isobutyl; R = ethoxy), turned out to be 12 times more active than the sulfonylurea (SU) glibenclamide (1). Activity was found to reside predominantly in the (S)- enantiomers. Compared with the SUs 1 and 2 (glimepiride), the most active enantiomer, (S)-6al (AG-EE 623 ZW; repaglinide; ED50 = 10 μg/kg po), is 25 and 18 times more active. Repaglinide turned out to be a useful therapeutic for type 2 diabetic patients; approval was granted recently by the FDA and the EMEA. From investigations on the pharmacophoric groups in compounds of type 5 and 6, it was concluded that in addition to the two already known - the acidic group (COOH; S02NH) and the amidic spacer (CONH; NHCO) - the ortho residue R1 (alkyleneimino; alkoxy; oxo) must be regarded as a third one. A general pharmacophore model suitable for hypoglycemic benzoic acid derivatives, SUs, and sulfonamides is proposed (Figure 6). Furthermore, from superpositions of low-energy conformations (LECs) of 1, 2, and (S)-6al, it was concluded that a common binding conformation (LEC II; Figure 10B) may exist and that differences in binding to the SU receptor and in the mechanism of insulin release between repaglinide and the two SUs may be due to specific hydrophobic differences.