N,N-Dimethylglycine Chemical Properties

Melting point:

178-182 °C(lit.)

Boiling point:

193.35°C (rough estimate)

Density 

1 g/cm³

refractive index 

1.4674 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Methanol (Slightly), Water (Slightly)

pka

9.89(at 25℃)

form 

Crystalline Powder

color 

White to slightly yellow

Water Solubility 

soluble

Sensitive 

Hygroscopic

Merck 

14,3244

BRN 

1700261

InChIKey

FFDGPVCHZBVARC-UHFFFAOYSA-N

CAS DataBase Reference

1118-68-9(CAS DataBase Reference)

EPA Substance Registry System

Glycine, N,N-dimethyl- (1118-68-9)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

24/25-36/37-26

WGK Germany 

3

RTECS 

MB9865000

F 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29224999

Toxicity

rat,LD50,oral,> 650mg/kg (650mg/kg),BEHAVIORAL: ATAXIABLOOD: CHANGES IN SPLEENGASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA",Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 199, 1992.

MSDS

• Language:English Provider:N,N-Dimethylglycine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N,N-Dimethylglycine Usage And Synthesis

Description

N,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.

Chemical Properties

white to slightly yellow crystalline powder

History

N,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.

Synthesis

The preparation method of N,N-Dimethylglycine comprises the following steps of: preparing N,N-dimethyl amino acetonitrile by taking hydroxyacetonitrile and dimethylamine as raw materials, obtaining an N,N-dimethylglycine crude product by alkalizing the reaction liquid with an inorganic base and neutralizing the reaction liquid with an organic acid on the basis of N,N-dimethyl amino acetonitrile reaction liquid, and finally separating and purifying the N,N-dimethylglycine crude product to obtain the high-quality N,N-dimethylglycine product.

Uses

N,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.

Application

N, N-dimethylglycine (DMG) is a tertiary amino acid that naturally occurs as an intermediate metabolite in choline-to-glycine metabolism. It has been suggested for use as an athletic performance enhancer, immunostimulant, and a treatment for autism, epilepsy, or mitochondrial disease . Published studies on the subject have shown little to no difference between DMG treatment and placebo in autism spectrum disorders.

Definition

ChEBI: 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.

Preparation

N,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.

General Description

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

Biochem/physiol Actions

N,N-Dimethylglycine (DMG) is a natural N-methylated glycine that is used in comparative analysis with other N-methylated glycines such as sarcosine and βine. N,N-Dimethylglycine is used in the development of glycine-based ionic liquids and emulsifiers. N,N-Dimethylglycine is potentially useful as a biomarker of protein degradation in COPD patients. DMG is used as a substrate to identify, differentiate and characterize amino acid methyltransferase(s).

References

J. K. Kern, V. S. Miller, L. Cauller, R. Kendall, J. Mehta, M. Dodd, Effectiveness of N,N-Dimethylglycine in Autism and Pervasive Developmental Disorder, Journal of Child Neurology, 2001, vol. 16, pp. 169-173

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