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N,N-Dimethylglycine

  • CAS No.: 1118-68-9
  • Purity: 99%
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  • Molecular Formula: C4H9NO2
  • Molecular Weight: 103.121
  • Appearance/Colour: white to slightly yellow crystalline powder 
  • Vapor Pressure: 0.556mmHg at 25°C 
  • Melting Point: 178-182 °C(lit.) 
  • Refractive Index: 1.448 
  • Boiling Point: 175.2 °C at 760 mmHg 
  • PKA: 9.89(at 25℃) 
  • Flash Point: 59.8 °C 
  • PSA: 40.54000 
  • Density: 1.069 g/cm3 
  • LogP: -0.36740 

N,N-Dimethylglycine(Cas 1118-68-9) Usage

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.

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).

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.

General Description

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

InChI:InChI=1/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)

1118-68-9 Relevant articles

Novel Tween 20 derivatives enable the formation of efficient pH-sensitive drug delivery vehicles for human hepatoblastoma

Masotti, Andrea,Vicennati, Paola,Alisi, Anna,Marianecci, Carlotta,Rinaldi, Federica,Carafa, Maria,Ortaggi, Giancarlo

, p. 3021 - 3025 (2010)

We describe the synthesis, the physicoch...

An Anomalous Eschweiler-Clarke Reaction

Rahal, Said,Badache, Leila

, p. 3847 - 3848 (1991)

Reaction of β-alanine 1 with formaldehyd...

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Pearson,Bruton

, p. 864 (1951)

-

-

Nardi,D. et al.

, p. 990 - 992 (1971)

-

Properties of monolayers of normal alkyl betaines at the air-water interface.

Evans,Pilpel

, p. 1228 - 1232 (1969)

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Electroactivated alkylation of amines with alcohols: Via both direct and indirect borrowing hydrogen mechanisms

Appiagyei, Benjamin,Bhatia, Souful,Keeney, Gabriela L.,Dolmetsch, Troy,Jackson, James E.

supporting information, p. 860 - 869 (2020/02/21)

A green, efficient N-alkylation of amine...

A New Microbial Pathway for Organophosphonate Degradation Catalyzed by Two Previously Misannotated Non-Heme-Iron Oxygenases

Rajakovich, Lauren J.,Pandelia, Maria-Eirini,Mitchell, Andrew J.,Chang, Wei-Chen,Zhang, Bo,Boal, Amie K.,Krebs, Carsten,Bollinger, J. Martin

, p. 1627 - 1647 (2019/03/19)

The assignment of biochemical functions ...

Characterization of N,N-dimethyl amino acids by electrospray ionization-tandem mass spectrometry

Naresh Chary,Sudarshana Reddy,Kumar, Ch. Dinesh,Srinivas,Prabhakar

, p. 771 - 781 (2015/08/18)

Methylation is an essential metabolic pr...

Novel Isobaric Tandem Mass Tags for Quantitative Proteomics and Peptidomics

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Sheet 4, (2013/04/10)

Compositions and methods of tagging pept...

1118-68-9 Process route

L-homocysteine
6027-13-0

L-homocysteine

betaine
107-43-7

betaine

dimethylaminoacetic acid
1118-68-9

dimethylaminoacetic acid

L-methionine
63-68-3,26062-47-5,58576-49-1

L-methionine

Conditions
Conditions Yield
in Gegenwart von Leber-Praeparaten;
sarcosine
107-97-1,25951-24-0

sarcosine

formaldehyd
50-00-0,30525-89-4,61233-19-0

formaldehyd

dimethylaminoacetic acid
1118-68-9

dimethylaminoacetic acid

methylamine
74-89-5

methylamine

Conditions
Conditions Yield
With Carbonate buffer; Product distribution; controlled potential electrolysis: glassy-carbon plate electrode, pH 10;

1118-68-9 Upstream products

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    2-(N,N-dimethylamino)ethanol

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    L-homocysteine

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    betaine

  • 926-64-7
    926-64-7

    N,N-Dimethylamino acetonitrile

1118-68-9 Downstream products

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    (Carboxylatomethyl)docosyldimethylammonium

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    30450-79-4

    O-(N,N-Dimethylglycyl)glykolsaeure-benzylester

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