 | |
 | |
| Names | |
|---|---|
| IUPAC name N,N-Dimethylglycine | |
| Systematic IUPAC name (Dimethylamino)acetic acid | |
| Identifiers | |
3D model (JSmol) | |
| 1700261 | |
| ChEBI | |
| ChemSpider |
|
| DrugBank |
|
| ECHA InfoCard | 100.012.971 |
| EC Number |
|
| 82215 | |
| KEGG |
|
| MeSH | dimethylglycine |
| RTECS number |
|
| UNII | |
| |
| |
| Properties | |
| C4H9NO2 | |
| Molar mass | 103.121 g·mol−1 |
| Appearance | White crystals |
| Odor | Odourless |
| Density | 1.069 g/mL |
| Melting point | 178 to 182 °C (352 to 360 °F; 451 to 455 K) |
| Boiling point | 175.2 °C (347.4 °F; 448.3 K) |
| Hazards | |
| GHS labelling: | |
 | |
| Warning | |
| H302 | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | >650 mg kg−1(oral, rat) |
| Related compounds | |
Related alkanoic acids | |
Related compounds | Dimethylacetamide |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Dimethylglycine (DMG) is a derivative of theamino acidglycine with the structural formula (CH3)2NCH2COOH. It can be found in beans and liver, and has a sweet taste. It can be formed fromtrimethylglycine upon the loss of one of itsmethyl groups. It is also a byproduct of the metabolism ofcholine.
When DMG was first discovered, it was referred to as Vitamin B16, but, unlike trueB vitamins, deficiency of DMG in the diet does not lead to any ill-effects and it is synthesized by the human body in thecitric acid cycle meaning it does not meet the definition of avitamin.
Dimethylglycine has been suggested for use as anathletic performance enhancer,immunostimulant, and a treatment forautism,epilepsy, ormitochondrial disease.[1] There is no evidence that dimethylglycine is effective for treating mitochondrial disease.[2] Published studies on the subject have shown little to no difference between DMG treatment andplacebo in autism spectrum disorders.[3][4]
Dimethylglycine has been found to act as anagonist of theglycine site of theNMDA receptor.[5]
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 glycinevia theEschweiler–Clarke reaction. In this reaction,glycine is treated with aqueousformaldehyde informic acid that serves as both solvent and reductant. Hydrochloric acid is added thereafter to give the hydrochloride salt. The free amino acid may have been obtained by neutralization of the acid salt, which has been performed withsilver oxide.[6]
