Dimethylglycine
Names
IUPAC name
Other names N,N-Dimethylglycine
Identifiers
1118-68-9
3DMet
1700261
ChEBI
ChemSpider	653
DrugBank
ECHA InfoCard	100.012.971
EC Number	214-267-8
82215
KEGG	C01026
MeSH	dimethylglycine
RTECS number
CompTox Dashboard(EPA)
InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)
CN(C)CC(O)=O
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 pictograms
GHS Signal word	Warning
H302
Lethal dose or concentration (LD, LC):
>650 mg kg⁻¹(oral, rat)
Related compounds
Related alkanoic acids
Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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Dimethylglycine (DMG) is a derivative of the amino acid glycine with the structural formula (CH 3) 2 NCH 2 COOH. 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. Sometime programs are distributed on a.dmg, which is a disk image containing the.app and perhaps a Readme. Apps downloaded outside of the App Store might not run unless you secondary-click on them to run, and then grant permission. This is a security feature. (It's similar in appearance to the Windows UAC, but it works differently.). The Dungeon Master's Guide is a book published at the very beginning of the 4e line. It is a comprehensive rules overview. The Dungeon Master's kit is a box set part of the Essentials line that contains a Dungeon Master's book, an adventure (Reavers of Harkenwald (which is a great adventure btw)) and a set of tokens. Sep 03, 2018 Removing the sleeve reveals a surprisingly nice, naturally colored cardboard box that is emblazoned with BGVP's new logo that I'm quite fond of. Lifting the lid of the box you find two smaller boxes. The top houses the DMG's ear pieces on display under appropriately shaped viewing windows.

Dimethylglycine (DMG) is a derivative of the amino acidglycine 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] There is no evidence that dimethylglycine is effective for treating mitochondrial disease.^[3] Published studies on the subject have shown little to no difference between DMG treatment and placebo in autism spectrum disorders.^[4]^[5]

Biological activity[edit]

Dimethylglycine has been found to act as an agonist of the glycine site of the NMDA receptor.^[6]

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 have been obtained by neutralization of the acid salt, which has been performed with silver oxide.^[7]

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

References[edit]

What Is The Difference Between Dmg S And Dmg M X

^'dimethylglycine - Compound Summary'. PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 24 April 2012.
^'Dimethylglycine'. About Herbs, Botanicals & Other Products. Memorial Sloan–Kettering Cancer Center. December 8, 2009.
^Pfeffer, Gerald; Majamaa, Kari; Turnbull, Douglass M.; Thorburn, David; Chinnery, Patrick F. (2012-04-18). 'Treatment for mitochondrial disorders'. The Cochrane Database of Systematic Reviews (4): CD004426. doi:10.1002/14651858.CD004426.pub3. ISSN1469-493X. PMID22513923.
^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. PMID10425581.
^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. PMID11305684.
^Lin, Jen-Cheng; Chan, Ming-Huan; Lee, Mei-Yi; Chen, Yi-Chyan; Chen, Hwei-Hsien (2016). 'N,N-dimethylglycine differentially modulates psychotomimetic and antidepressant-like effects of ketamine in mice'. Progress in Neuro-Psychopharmacology and Biological Psychiatry. 71: 7–13. doi:10.1016/j.pnpbp.2016.06.002. ISSN0278-5846. PMID27296677.
^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.

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Dimethylgly