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Details

Stereochemistry ACHIRAL
Molecular Formula C4H9NO2
Molecular Weight 103.1198
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N,N-DIMETHYLGLYCINE

SMILES

CN(C)CC(O)=O

InChI

InChIKey=FFDGPVCHZBVARC-UHFFFAOYSA-N
InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)

HIDE SMILES / InChI
Molecular Formula C4H9NO2
Molecular Weight 103.1198
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

N,N-dimethylglycine or dimethylglycine (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. DMG has been found acting at glycine binding site of the N-methyl-d-aspartate receptor (NMDAR). DMG has had wide acceptance as a nonfuel nutrient; presumably it enhances oxygen utilization by tissue and complexes free radicals. There were published studies, which have shown little to no difference between DMG treatment and placebo in autism spectrum disorders and the same no effect was observed in case of investigated DMG for epilepsy. This compound was also suggested to use to improve the athletic performance enhancer, but this usage was ineffective as well.

CNS Activity

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
The salt-induced ABC transporter Ota of the methanogenic archaeon Methanosarcina mazei Gö1 is a glycine betaine transporter.
2007-12
Sex differences in the control of plasma concentrations and urinary excretion of glycine betaine in patients attending a lipid disorders clinic.
2007-11
The association of betaine, homocysteine and related metabolites with cognitive function in Dutch elderly people.
2007-11
Large-scale population-based metabolic phenotyping of thirteen genetic polymorphisms related to one-carbon metabolism.
2007-09
Structure-activity and high-content imaging analyses of novel tubulysins.
2007-08
Metabolism of low-dose inorganic arsenic in a central European population: influence of sex and genetic polymorphisms.
2007-07
Solid-phase synthesis of a peptide derivative of thymosin alpha1 and initial studies on its (99m)Tc-radiolabelling.
2007-07
Immunomodulation of murine collagen-induced arthritis by N, N-dimethylglycine and a preparation of Perna canaliculus.
2007-06-11
Mechanistic aspects and redox properties of hyperthermophilic L-proline dehydrogenase from Pyrococcus furiosus related to dimethylglycine dehydrogenase/oxidase.
2007-04
Modulation of the homocysteine-betaine relationship by methylenetetrahydrofolate reductase 677 C->t genotypes and B-vitamin status in a large-scale epidemiological study.
2007-04
Osmotic regulation of betaine homocysteine-S-methyltransferase expression in H4IIE rat hepatoma cells.
2007-04
Beyond lipids, pharmacological PPARalpha activation has important effects on amino acid metabolism as studied in the rat.
2007-04
Natural approaches to epilepsy.
2007-03
The organic osmolytes betaine and proline are transported by a shared system in early preimplantation mouse embryos.
2007-01
A top-down systems biology view of microbiome-mammalian metabolic interactions in a mouse model.
2007
Characterization of oxysterols by electrospray ionization tandem mass spectrometry after one-step derivatization with dimethylglycine.
2007
In silico experimentation with a model of hepatic mitochondrial folate metabolism.
2006-12-06
Critical active-site residues identified by site-directed mutagenesis in Pseudomonas aeruginosa phosphorylcholine phosphatase, a new member of the haloacid dehalogenases hydrolase superfamily.
2006-12
Effects of substrate and potassium on the betaine-synthesizing enzyme glycine sarcosine dimethylglycine N-methyltransferase from a halophilic methanoarchaeon Methanohalophilus portucalensis.
2006-12
Mechanism of FAD reduction and role of active site residues His-225 and Tyr-259 in Arthrobacter globiformis dimethylglycine oxidase: analysis of mutant structure and catalytic function.
2006-09-19
Heterotetrameric sarcosine oxidase: structure of a diflavin metalloenzyme at 1.85 A resolution.
2006-07-28
Mild and nonracemizing conditions for Ullmann-type diaryl ether formation between aryl iodides and tyrosine derivatives.
2006-07-07
The effects of the oral, pan-VEGF-R kinase inhibitor CEP-7055 and chemotherapy in orthotopic models of glioblastoma and colon carcinoma in mice.
2006-07
Design and synthesis of novel sulfonamide-containing bradykinin hB2 receptor antagonists. 1. Synthesis and SAR of alpha,alpha-dimethylglycine sulfonamides.
2006-06-15
N,N-dimethyl-beta-alanine as an inexpensive and efficient ligand for palladium-catalyzed Heck reaction.
2006-06-08
Effects of diabetes and insulin on betaine-homocysteine S-methyltransferase expression in rat liver.
2006-05
Treatment for mitochondrial disorders.
2006-01-25
Mining literature for a comprehensive pathway analysis: a case study for retrieval of homocysteine related genes for genetic and epigenetic studies.
2006-01-23
Causes of hyperhomocysteinemia in patients with chronic kidney diseases.
2006-01
Weak antiferromagnetic interactions in hydronium diaqua-1kappaO,2kappaO-trichloro-1kappaCl,2kappa2Cl-mu-dimethylglycinato-1kappaO:2kappa2O',N-dimethylglycinato-1kappa2N,O-dicuprate(II).
2005-12
NMR spectroscopic-based metabonomic investigation on the acute biochemical effects induced by Ce(NO3)3 in rats.
2005-11
Stabilization of non-productive conformations underpins rapid electron transfer to electron-transferring flavoprotein.
2005-08-26
Gas phase synthesis and reactivity of Agn+ and Ag(n-1)H+ cluster cations.
2005-08-21
Sexual dimorphism in urinary metabolite profiles of Han Wistar rats revealed by nuclear-magnetic-resonance-based metabonomics.
2005-08-15
Gas-phase structure of N,N-dimethylglycine.
2005-08-12
Organic compatible solutes of halotolerant and halophilic microorganisms.
2005-08-04
Di-mu-chloro-1:2kappa2Cl;3:4kappa2Cl-hexachloro-1kappa3Cl,4kappa3Cl-tetra-mu-dimethylglycine-2:3kappa8O:O'-tetracopper(II).
2005-08
Crystal structure of DMGO provides a prototype for a new tetrahydrofolate-binding fold.
2005-08
Guanine and plasmid DNA binding of mono- and trinuclear fac-[Re(CO)3]+ complexes with amino acid ligands.
2005-08
Crystal structure of heterotetrameric sarcosine oxidase from Corynebacterium sp. U-96.
2005-07-29
A combined (1)H NMR and HPLC-MS-based metabonomic study of urine from obese (fa/fa) Zucker and normal Wistar-derived rats.
2005-07-01
Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles.
2005-06-24
Identification, cloning, and expression of Pseudomonas aeruginosa phosphorylcholine phosphatase gene.
2005-05
Statistical total correlation spectroscopy: an exploratory approach for latent biomarker identification from metabolic 1H NMR data sets.
2005-03-01
The structure of the TrmE GTP-binding protein and its implications for tRNA modification.
2005-01-12
Betaine: a key modulator of one-carbon metabolism and homocysteine status.
2005
Profiles of metabolites and gene expression in rats with chemically induced hepatic necrosis.
2005
A novel gamma-N-methylaminobutyrate demethylating oxidase involved in catabolism of the tobacco alkaloid nicotine by Arthrobacter nicotinovorans pAO1.
2004-12
Chemical aspects of amine oxidation by flavoprotein enzymes.
2004-12
Effects of intravenous betaine on methionine-loading-induced plasma homocysteine elevation in rats.
2004-11
Patents

Patents

04163058
3
04965263
2
05059609
3
06660744
6
06716861
6
07135475
3
07192974
5
07211594
3
07384980
2
07419988
4
07504413
3
07601719
2
07605266
4
07622487
3
07642256
2
07645769
2
07696352
4
07790885
4
07855230
2
07906643
2
08058261
2
08101608
2
08158623
2
08222416
2
08431607
3
08466188
3
08569281
2
08658794
2
08697604
2
08697742
2
08716498
4
08759365
3
08759535
3
08809369
2
08835469
2

Sample Use Guides

In Vivo Use Guide
epilepsy: Dosage was 300 mg/day for the first 14 days and then 600 mg/day up to 28 days
Route of Administration: Oral
In Vitro Use Guide
It was investigated the effects of N, N-Dimethylglycine (DMG) on the development of in vitro produced (IVP) bovine embryos. IVP embryos were obtained by in vitro fertilization of in vitro matured oocytes for 6 h. In Experiment 1, IVP embryos were cultured in mSOFaa supplemented with bovine serum albumin but without glucose (SOF1) for 4 days, transferred to mSOFaa (with 5% fetal bovine serum and 1.5 mM glucose; SOF2) supplemented with 0 (control), 0.1,1 or 10 microM DMG and cultured for an additional 7 days (11 days in total) to assess their development in vitro. When cultured in the medium with 0.1 microM DMG, a significantly higher number of IVP embryos developed to the blastocyst and hatched blastocyst stages (40.3 and 40.8%, respectively) compared with the other groups (18.7-31.0% and 15.0-28.7%, respectively; P<0.05, analysis of variance). In Experiment 2, IVP embryos were cultured in SOF1 with or without 0.1 microM DMG for 4 days, transferred to SOF2 with or without 0.1 microM DMG and further cultured as in Experiment 1; DMG was added to either SOF1 or SOF2 and to both of them to assess its exposure effects on embryo development. When cultured continuously with DMG for 11 days, significantly higher rates of IVP embryos developed into blastocyst and hatched blastocyst stages (39.0 and 47.7%, respectively) compared with the other groups (31.0-32.2% and 29.5-31.0%, respectively; P<0.05). In Experiment 3, we examined developmental speed of IVP embryos cultured with or without addition of 0.1 microM DMG to IVC medium after 7 days of IVC.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:59:08 GMT 2025
Edited
by admin
on Mon Mar 31 19:59:08 GMT 2025
Record UNII
7797M4CPPA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
N,N-DIMETHYLGLYCINE [MI]
Preferred Name English
N,N-DIMETHYLGLYCINE
MI   WHO-DD  
Systematic Name English
DIMETHYLGLYCINE
Systematic Name English
2-(DIMETHYLAMINO)ACETIC ACID
Systematic Name English
N-METHYLSARCOSINE
Systematic Name English
N,n-dimethylglycine [WHO-DD]
Common Name English
GLYCINE, N,N-DIMETHYL-
Systematic Name English
Classification Tree Code System Code
DSLD 1719 (Number of products:60)
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
Code System Code Type Description
WIKIPEDIA
DIMETHYLGLYCINE
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
RXCUI
1313173
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY RxNorm
FDA UNII
7797M4CPPA
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
CHEBI
17724
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
CHEBI
58251
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
ECHA (EC/EINECS)
214-267-8
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
EVMPD
SUB22305
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
EPA CompTox
DTXSID6074336
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
CAS
1118-68-9
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
DRUG BANK
DB02083
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
DAILYMED
7797M4CPPA
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
PUBCHEM
673
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
MERCK INDEX
m4539
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY Merck Index
SMS_ID
100000085996
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
MESH
C025138
Created by admin on Mon Mar 31 19:59:08 GMT 2025 , Edited by admin on Mon Mar 31 19:59:08 GMT 2025
PRIMARY
Related Record Type Details
Structure of N,N-DIMETHYLGLYCINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of N,N-DIMETHYLGLYCINE
ACTIVE MOIETY
NIH
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