dimethylglycine
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443693225
| ImageFile = Dimethylglycine.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 140
| ImageAlt = Skeletal formula of dimethylglycine
| ImageFile1 = Dimethylglycine zwitterion 3D ball.png
| ImageSize1 = 160
| ImageAlt1 = Ball-and-stick model of the dimethylglycine molecule as a zwitterion
| SystematicName = (Dimethylamino)acetic acid
| IUPACName = N,N-Dimethylglycine
|Section1={{Chembox Identifiers
| CASNo = 1118-68-9
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7797M4CPPA
| PubChem = 673
| ChemSpiderID = 653
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 214-267-8
| DrugBank = DB02083
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| KEGG = C01026
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = dimethylglycine
| ChEBI = 17724
| ChEBI_Ref = {{ebicite|changed|EBI}}
| RTECS = MB9865000
| Beilstein = 1700261
| Gmelin = 82215
| 3DMet = B00224
| SMILES = CN(C)CC(O)=O
| StdInChI = 1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FFDGPVCHZBVARC-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=4 | H=9 | N=1 | O=2
| Appearance = White crystals
| Odor = Odourless
| Density = 1.069 g/mL
| BoilingPtC = 175.2
| MeltingPtC = 178 to 182
}}
|Section3={{Chembox Hazards
| GHSPictograms = {{gHS exclamation mark}}
| GHSSignalWord = WARNING
| HPhrases = {{h-phrases|302}}
| LD50 = >650 mg kg−1 (oral, rat)
}}
|Section4={{Chembox Related
| OtherFunction_label = alkanoic acids
| OtherFunction = {{unbulleted list|Sarcosine|Glycocyamine|Creatine|N-Methyl-D-aspartic acid|beta-Methylamino-L-alanine|Guanidinopropionic acid}}
| OtherCompounds = Dimethylacetamide
}}
}}
Dimethylglycine (DMG) is a derivative of the amino acid glycine with the structural formula (CH3)2NCH2COOH. It can be found in beans and liver, and has a sweet taste. 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 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.{{cite web |title=Dimethylglycine |url=http://www.mskcc.org/mskcc/html/69204.cfm |publisher=Memorial Sloan–Kettering Cancer Center |date=December 8, 2009 |work=About Herbs, Botanicals & Other Products}} There is no evidence that dimethylglycine is effective for treating mitochondrial disease.{{Cite journal|last1=Pfeffer|first1=Gerald|last2=Majamaa|first2=Kari|last3=Turnbull|first3=Douglass M.|last4=Thorburn|first4=David|last5=Chinnery|first5=Patrick F.|date=2012-04-18|title=Treatment for mitochondrial disorders|journal=The Cochrane Database of Systematic Reviews|volume=2012 |issue=4|pages=CD004426|doi=10.1002/14651858.CD004426.pub3|issn=1469-493X|pmid=22513923|pmc=7201312}} Published studies on the subject have shown little to no difference between DMG treatment and placebo in autism spectrum disorders.{{cite journal |vauthors=Bolman WM, Richmond JA |title=A double-blind, placebo-controlled, crossover pilot trial of low-dose dimethylglycine in patients with autistic disorder |journal=Journal of Autism and Developmental Disorders |volume=29 |issue=3 |pages=191–4 |date=June 1999 |pmid=10425581 |doi=10.1023/A:1023023820671|s2cid=6993427 }}{{cite journal |vauthors=Kern JK, Miller VS, Cauller PL, Kendall PR, Mehta PJ, Dodd M |title=Effectiveness of N,N-dimethylglycine in autism and pervasive developmental disorder |journal=Journal of Child Neurology |volume=16 |issue=3 |pages=169–73 |date=March 2001 |pmid=11305684 |doi=10.1177/088307380101600303 |s2cid=25016913 }}
Biological activity
Dimethylglycine has been found to act as an agonist of the glycine site of the NMDA receptor.{{cite journal|last1=Lin|first1=Jen-Cheng|last2=Chan|first2=Ming-Huan|last3=Lee|first3=Mei-Yi|last4=Chen|first4=Yi-Chyan|last5=Chen|first5=Hwei-Hsien|title=N,N-dimethylglycine differentially modulates psychotomimetic and antidepressant-like effects of ketamine in mice|journal=Progress in Neuro-Psychopharmacology and Biological Psychiatry|volume=71|year=2016|pages=7–13|pmid=27296677|issn=0278-5846|doi=10.1016/j.pnpbp.2016.06.002|s2cid=4817868}}
Preparation
This compound is commercially available as the free form amino acid, and as the hydrochloride salt [{{CAS|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.{{cite journal | doi = 10.1021/ja01338a041 | year = 1933 | title = The Action of Formaldehyde on Amines and Amino Acids | last1 = Clarke | first1 = H. T. | last2 = Gillespie | first2 = H. B. | last3 = Weisshaus | first3 = S. Z. | journal = Journal of the American Chemical Society | volume = 55 | issue = 11 | pages = 4571}}
:H2NCH2COOH + 2 CH2O + 2 HCOOH → (CH3)2NCH2COOH + 2 CO2 + 2 H2O