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
• Article Data: 8

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

Definition

ChEBI: A non-proteinogenic L-alpha-amino acid that is L-alanine in which one of the methyl hydrogens is replaced by a methylamino group. A non-proteinogenic amino acid produced by cyanobacteria, it is a neurotoxi that has been postulated as a possible cause of neurodegenerative disorders of aging such as Alzheimer's disease, amyotrophic lateral sclerosis, and the amyotrophic lateral sclerosis/parkinsonism-dementia complex (ALS-PDC) syndrome of Guam.

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

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

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.

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.

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.