Dimethylglycine

Dimethylglycine

Names
IUPAC name 2-(Dimethylamino)acetic acid[1]
Other names N,N-Dimethylglycine
Identifiers
3DMet	B00224
Beilstein Reference	1700261
CAS Registry Number	1118-68-9 Y
ChEBI	CHEBI:17724 N
ChemSpider	653 Y
DrugBank	DB02083 Y
EC number	214-267-8
Gmelin Reference	82215
InChI InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7) Y Key: FFDGPVCHZBVARC-UHFFFAOYSA-N Y
Jmol-3D images	Image Image
KEGG	C01026 Y
MeSH	dimethylglycine
PubChem	673
RTECS number	MB9865000
SMILES CN(C)Cc(:[o]):[oH] CN(C)CC(O)=O
Properties
Molecular formula	C4H9NO2
Molar mass	103.12 g·mol−1
Appearance	White crystals
Odor	Odourless
Density	1.069 g/mL
Melting point	178 °C (352 °F; 451 K)
Boiling point	175.2 °C (347.4 °F; 448.3 K)
Hazards
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H302
LD50 (Median lethal dose)	>650 mg kg−1 (oral, rat)
Related compounds
Related alkanoic acids	Sarcosine Glycocyamine Creatine N-Methyl-D-aspartic acid beta-Methylamino-L-alanine Guanidinopropionic acid
Related compounds	Dimethylacetamide
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Dimethylglycine is a derivative of the amino acid glycine with the structural formula (CH₃)₂NCH₂COOH. It can be 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 and it is synthesized by the human body in the citric acid (or Krebs) cycle meaning it does not meet the definition of a vitamin.

Uses

Dimethylglycine has been suggested for use as an athletic performance enhancer, immunostimulant, and a treatment for autism, epilepsy, or mitochondrial disease.^[2][3] Published studies on the subject have shown little to no difference between DMG treatment and placebo in autism spectrum disorders.^[4][5]

Preparation

This compound 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.^[6]

H₂NCH₂COOH + 2 CH₂O + 2 HCOOH → (CH₃)₂NCH₂COOH + 2 CO₂ + 2 H₂O

References