Dimethylglycine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Dimethylglycine
Skeletal formula of dimethylglycine
Identifiers
CAS number 1118-68-9 YesY
PubChem 673
ChemSpider 653 YesY
EC number 214-267-8
DrugBank DB02083
KEGG C01026 YesY
MeSH dimethylglycine
ChEBI CHEBI:17724 N
RTECS number MB9865000
Beilstein Reference 1700261
Gmelin Reference 82215
3DMet B00224
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C4H9NO2
Molar mass 103.12 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 pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
GHS hazard statements H302
LD50 >650 mg kg−1 (oral, rat)
Related compounds
Related alkanoic acids
Related compounds Dimethylacetamide
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/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[edit]

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[edit]

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[edit]

  1. ^ "dimethylglycine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 24 April 2012. 
  2. ^ "Dimethylglycine". About Herbs, Botanicals & Other Products. Memorial Sloan–Kettering Cancer Center. December 8, 2009. 
  3. ^ Chinnery P, Majamaa K, Turnbull D, Thorburn D (2006). "Treatment for mitochondrial disorders". In Chinnery, PF. Cochrane Database of Systematic Reviews (Online) (1): CD004426. doi:10.1002/14651858.CD004426.pub2. PMID 16437486. 
  4. ^ Bolman WM, Richmond JA (June 1999). "A double-blind, placebo-controlled, crossover pilot trial of low-dose dimethylglycine in patients with autistic disorder". Journal of Autism and Developmental Disorders 29 (3): 191–4. doi:10.1023/A:1023023820671. PMID 10425581. 
  5. ^ Kern JK, Miller VS, Cauller PL, Kendall PR, Mehta PJ, Dodd M (March 2001). "Effectiveness of N,N-dimethylglycine in autism and pervasive developmental disorder". Journal of Child Neurology 16 (3): 169–73. doi:10.1177/088307380101600303. PMID 11305684. 
  6. ^ Clarke, H. T.; Gillespie, H. B.; Weisshaus, S. Z. (1933). "The Action of Formaldehyde on Amines and Amino Acids". Journal of the American Chemical Society 55 (11): 4571. doi:10.1021/ja01338a041.