N,N-Dimethylglycine

DescriptionN,N-Dimethylglycine (DMG) is a N-methylated product of the amino acid glycine. It is found in beans and liver. It can be formed from trimethylglycine upon the loss of one of its methyl groups. It is also a byproduct of the metabolism of choline. When DMG was first discovered, it was referred to as vitamin B16, but, unlike true B vitamins, deficiency of DMG in the diet does not lead to any ill-effects meaning it does not meet the definition of a vitamin. It is used in comparative analysis with other N-methylated glycines. N,N-Dimethylglycine is used in the development of glycine-based ionic liquids and emulsifiers, and as a substrate to identify, differentiate and characterize amino acid methyltransferase(s). It is potentially useful as a biomarker of protein degradation in COPD patients.

HistoryN,N-Dimethylglycine was discovered in 1943. It is found in some but not all formulations of pangamic acid (vitamin B15). Pangamic acid has been sold as a dietary supplement in the United States at least since the late 1970s, when the lay press celebrated its benefits. Although pangamic acid is also known as vitamin B16, it is not actually a vitamin because no deficiency state has been identified, and it has no known nutritional value.

UsesN,N-Dimethylglycine is used as an athletic performance enhancer and immunostimulant. It is also used in the treatment of autism, epilepsy and mitochondrial disease. It is also employed as a biomarker of protein degradation in chronic obstructive lung disease (COPD) patients. Further, it is used as a substrate to identify, differentiate and characterize amino acid methyltransferase. It plays an important role for the development of glycine-based ionic liquids and emulsifiers.

General DescriptionN,N-Dimethylglycine is a type of quaternary ammonium compound which exhibits a variety of biological effects.

PreparationN,N-Dimethylglycine is commercially available as the free form amino acid, and as the hydrochloride salt [2491-06-7 ]. DMG may be prepared by the alkylation of glycine via the Eschweiler–Clarke reaction. In this reaction, glycine is treated with aqueous formaldehyde in formic acid that serves as both solvent and reductant. Hydrochloric acid is added thereafter to give the hydrochloride salt. The free amino acid may been obtained by neutralization of the acid salt, which has been performed with silver oxide. H2NCH2COOH + 2 CH2O + 2 HCOOH →(CH3)2NCH2COOH + 2 CO2 + 2 H2O.

DefinitionChEBI: N,N-dimethylglycine is an N-methylglycine that is glycine carrying two N-methyl substituents. It has a role as a human metabolite, a Daphnia magna metabolite and a mouse metabolite. It is a N-methyl-amino acid and a member of N-methylglycines. It is a tautomer of a N,N-dimethylglycine zwitterion.