Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:53 UTC
HMDB IDHMDB00092
Secondary Accession NumbersNone
Metabolite Identification
Common NameDimethylglycine
DescriptionDimethylglycine (DMG) is an amino acid derivative found in the cells of all plants and animals and can be obtained in the diet in small amounts from grains and meat. The human body produces DMG when metabolizing choline into Glycine. Dimethylglycine that is not metabolized in the liver is transported by the circulatory system to body tissue. Dimethylglycine was popular with Russian athletes and cosmonauts owing to its reputed ability to increase endurance and reduce fatigue. DMG is also a byproduct of homocysteine metabolism. Homocysteine and betaine are converted to methionine and N, N-dimethylglycine by betaine-homocysteine methyltransferase.
Structure
Thumb
Synonyms
  1. (Dimethylamino)acetate
  2. (Dimethylamino)acetic acid
  3. 2-(Dimethylamino)acetate
  4. 2-(Dimethylamino)acetic acid
  5. Dimethylglycine
  6. N,N-Dimethylaminoacetate
  7. N,N-Dimethylaminoacetic acid
  8. N,N-Dimethylglycine
  9. N-Methylsarcosine N,N-dimethyl-Glycine
Chemical FormulaC4H9NO2
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
IUPAC Name2-(dimethylamino)acetic acid
Traditional IUPAC Namedimethylglycine
CAS Registry Number1118-68-9
SMILES
CN(C)CC(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)
InChI KeyFFDGPVCHZBVARC-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • amino acid zwitterion(ChEBI)
Substituents
  • Carboxylic Acid
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction
  • Component of Glycine, serine and threonine metabolism
  • Component of Methionine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point185.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.91TSAI,RS ET AL. (1991)
Predicted Properties
PropertyValueSource
water solubility939 g/LALOGPS
logP-1.7ALOGPS
logP-3.1ChemAxon
logS0.96ALOGPS
pKa (strongest acidic)1.88ChemAxon
pKa (strongest basic)9.69ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area40.54ChemAxon
rotatable bond count2ChemAxon
refractivity26.07ChemAxon
polarizability10.49ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Betaine MetabolismSMP00123map00260
Glycine and Serine MetabolismSMP00004map00260
Methionine MetabolismSMP00033map00270
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified2.6 (1.8-3.7) uMAdult (>18 years old)BothNormal
BloodDetected and Quantified1.9 (1.1-3.4) uMAdult (>18 years old)BothNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal
UrineDetected and Quantified4.4 (1.6-10.4) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified6.2 (0.8-11.2) umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified3.4 (0.7-10.6) umol/mmol creatinineAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified5.4 (3.1-7.2) uMAdult (>18 years old)BothCommentKidney disease
BloodDetected and Quantified5.6 (4.8 - 10.1) uMAdult (>18 years old)BothCommentKidney disease
BloodDetected and Quantified4.8 (3.6-6.2) uMAdult (>18 years old)BothCommentKidney disease
Associated Disorders and Diseases
Disease References
Kidney disease
  • McGregor DO, Dellow WJ, Lever M, George PM, Robson RA, Chambers ST: Dimethylglycine accumulates in uremia and predicts elevated plasma homocysteine concentrations. Kidney Int. 2001 Jun;59(6):2267-72. Pubmed: 11380830
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021893
KNApSAcK IDNot Available
Chemspider ID653
KEGG Compound IDC01026
BioCyc IDDIMETHYL-GLYCINE
BiGG ID36652
Wikipedia LinkDimethylglycine
NuGOwiki LinkHMDB00092
Metagene LinkHMDB00092
METLIN ID277
PubChem Compound673
PDB IDDMG
ChEBI ID17724
References
Synthesis ReferenceLai, Mei-Chin; Wang, Chia-Chi; Chuang, Ming-Jen; Wu, Yen-Chi; Lee, Yu-Chien. Effects of substrate and potassium on the betaine-synthesizing enzyme glycine sarcosine dimethylglycine N-methyltransferase from a halophilic methanoarchaeon Methanohalophilus po
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Binzak BA, Vockley JG, Jenkins RB, Vockley J: Structure and analysis of the human dimethylglycine dehydrogenase gene. Mol Genet Metab. 2000 Mar;69(3):181-7. Pubmed: 10767172
  2. Binzak BA, Wevers RA, Moolenaar SH, Lee YM, Hwu WL, Poggi-Bach J, Engelke UF, Hoard HM, Vockley JG, Vockley J: Cloning of dimethylglycine dehydrogenase and a new human inborn error of metabolism, dimethylglycine dehydrogenase deficiency. Am J Hum Genet. 2001 Apr;68(4):839-47. Epub 2001 Feb 28. Pubmed: 11231903
  3. Moolenaar SH, Poggi-Bach J, Engelke UF, Corstiaensen JM, Heerschap A, de Jong JG, Binzak BA, Vockley J, Wevers RA: Defect in dimethylglycine dehydrogenase, a new inborn error of metabolism: NMR spectroscopy study. Clin Chem. 1999 Apr;45(4):459-64. Pubmed: 10102904
  4. Laryea MD, Steinhagen F, Pawliczek S, Wendel U: Simple method for the routine determination of betaine and N,N-dimethylglycine in blood and urine. Clin Chem. 1998 Sep;44(9):1937-41. Pubmed: 9732980
  5. McGregor DO, Dellow WJ, Lever M, George PM, Robson RA, Chambers ST: Dimethylglycine accumulates in uremia and predicts elevated plasma homocysteine concentrations. Kidney Int. 2001 Jun;59(6):2267-72. Pubmed: 11380830
  6. Look MP, Riezler R, Reichel C, Brensing KA, Rockstroh JK, Stabler SP, Spengler U, Berthold HK, Sauerbruch T: Is the increase in serum cystathionine levels in patients with liver cirrhosis a consequence of impaired homocysteine transsulfuration at the level of gamma-cystathionase? Scand J Gastroenterol. 2000 Aug;35(8):866-72. Pubmed: 10994627
  7. Cicek G, Vuorinen T, Stahle I, Stepanek P, Freudenberg N, Brandsch R: Coxsackievirus B3 infection induces anti-flavoprotein antibodies in mice. Clin Exp Immunol. 2000 Dec;122(3):404-9. Pubmed: 11122247
  8. Lever M, George PM, Dellow WJ, Scott RS, Chambers ST: Homocysteine, glycine betaine, and N,N-dimethylglycine in patients attending a lipid clinic. Metabolism. 2005 Jan;54(1):1-14. Pubmed: 15562374
  9. Xia JH, Yu KP, Liu CY, Pan Q, Zheng D, Dai HP: [Molecular clonging of the human dimethyglycine dehydrogenase-like gene (DMGDHL1) from the sarcosinemia critical region at 9q34] Yi Chuan Xue Bao. 1999;26(6):591-7. Pubmed: 10876657
  10. Jansen M, Hansen TA: Non-growth-associated demethylation of dimethylsulfoniopropionate by (homo)acetogenic bacteria. Appl Environ Microbiol. 2001 Jan;67(1):300-6. Pubmed: 11133459

Enzymes

Gene Name:
DMGDH
Uniprot ID:
Q9UI17
Reactions
Dimethylglycine + electron-transfer flavoprotein + Water unknown Sarcosine + Formaldehyde + reduced electron-transfer flavoproteindetails
Dimethylglycine + Electron-transferring flavoprotein + Water unknown Sarcosine + Formaldehyde + Reduced electron-transferring flavoproteindetails
Gene Name:
BHMT
Uniprot ID:
Q93088
Reactions
Trimethylammonioacetate + Homocysteine unknown Dimethylglycine + L-Methioninedetails
Gene Name:
BHMT2
Uniprot ID:
Q9H2M3
Reactions
Trimethylammonioacetate + Homocysteine unknown Dimethylglycine + L-Methioninedetails