Uses
N-Nitroso-N-methyl-4-aminobutyric acid EP reference standard is intended for use only as specifically prescribed in the European Pharmacopoeia.
It is also used to prepare N-Nitrosamines spiking solution to detect the concentration of N-nitrosamines in active substances by liquid chromatography coupled with mass spectrometry according to the monograph 20542of European Pharmacopoeia.
Definition
ChEBI: N-nitroso-N-methyl-4-aminobutyric acid is a nitrosamine that has methyl and 3-carboxypropyl substituents. It is a tobacco-derived nitrosamino acid that is a known animal and potential human carcinogen. It induces bladder transitional cell carcinomas in rats and has recently been identified as a contaminant in certain blood pressure medications. It has a role as a carcinogenic agent, a rat metabolite, a xenobiotic metabolite and a plant metabolite. It is a monocarboxylic acid and a nitrosamine.
Synthesis
Add 5.0 g (0.05 mol) of N-methylpyrrolidone to a 250 mL four-necked flask, add 50 g of toluene and stir to dissolve clear, .
Add 0.5 g of tetrabutylammonium bromide, add aqueous sodium hydroxide solution (sodium hydroxide: 4 g (0.1 mol); water: 40 g), raise temperature to
50 , stirring reaction 28h, liquid separation, organic phase discarded, aqueous phase with hydrochloric acid to adjust pH = 1.0, filtration, filtrate collection, filter cake discarded.
