N,N-Dimethylglycine

DMG · DIMETHYLGLYCINE · n-methylsarcosine · (DIMETHYLAMINO)ACETIC ACID · N-Me-Sar-OH · AKOS BB-5614 · N-DiMethylglycine · N,N-Dimthylglycine

https://huagongshe.com/en/chemical/673

Identifiers & Physical Properties

CAS No.	1118-68-9
Molecular formula	C4H9NO2
Average molar mass	103.12 g/mol
Monoisotopic mass	103.06332853 g/mol
SMILES	CN(C)CC(=O)O
InChIKey	FFDGPVCHZBVARC-UHFFFAOYSA-N
PubChem CID	673
ChEMBL	CHEMBL1232274
ChEBI	CHEBI:17724
EC No.	214-267-8
DTXSID	DTXSID6074336

Chemical & Physical Properties

XLogP	-2.9
Topological polar surface area	40.5
Hydrogen bond donors	1
Hydrogen bond acceptors	3
Rotatable bonds	2
Heavy atoms	7
Formal charge	0
Complexity	70
LogP (partition coefficient)	-2.91
Boiling point	63.9193.35°C (rough estimate)
Melting point	185.5185.5 °C178-182 °C(lit.)
Physical Description	Solid
Dissociation Constants	2.04
Collision Cross Section	119.7 Å² [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]116 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine]123.1 Å² [M+H]+
Density	1 g/cm3
Refractive index	1.4674 (estimate)
Storage conditions	Keep in dark place,Sealed in dry,Room Temperature
Solubility	Methanol (Slightly), Water (Slightly)soluble
pKa (acidity coefficient)	9.89(at 25℃)
Physical state	Crystalline Powder
Color	White to slightly yellow
Sensitivity	Hygroscopic
Merck	14,3244
BRN	1700261
InChI	1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)
InChIKey	FFDGPVCHZBVARC-UHFFFAOYSA-N
SMILES	CN(C)CC(O)=O
CAS DataBase Reference	1118-68-9(CAS DataBase Reference)
EWG's Food Scores	1
FDA UNII	7797M4CPPA
EPA Substance Registry System	Glycine, N,N-dimethyl- (1118-68-9)
UNSPSC Code	41116105
NACRES	NA.26
GHS pictogram	GHS07
Signal word	Warning
GHS hazard statements	H302
GHS precautionary statements	P301+P312a-P330-P501a-P264-P270-P301+P312+P330-P501
Hazard symbols	Xn,Xi
Risk statements (R)	22-36/37/38
Safety statements (S)	24/25-36/37-26
Water hazard class (WGK)	3
RTECS number	MB9865000
F	3
TSCA inventory status	TSCA listed
Hazard class	IRRITANT
Customs code	29224999
Storage class	11 - Combustible Solids
Toxicity	rat,LD50,oral,> 650mg/kg (650mg/kg),BEHAVIORAL: ATAXIABLOOD: CHANGES IN SPLEENGASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA",Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 199, 1992.
REACH registrations	Active

Safety & Regulations

GHS classification	This chemical does not meet GHS hazard criteria for 53.2% (58 of 109) of all reports.WarningH302 (46.8%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 109 reports by companies from 4 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 58 of 109 reports by companies.There are 3 notifications provided by 51 of 109 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Regulatory information	PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.Status: Active Update: 22-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/19838Dimethylglycine: Non hazardous
Hazard Classes and Categories	Acute Tox. 4 (46.8%)
F	3
Water hazard class (WGK)	3
TSCA inventory status	TSCA listed
RTECS number	MB9865000
Customs code	29224999
Toxicity	rat,LD50,oral,> 650mg/kg (650mg/kg),BEHAVIORAL: ATAXIABLOOD: CHANGES IN SPLEENGASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA",Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 199, 1992.
Risk statements (R)	22-36/37/38
Signal word	Warning
GHS pictogram	GHS07
Hazard symbols	Xn,Xi

Applications & Uses

Description

N,N-Dimethylglycine (DMG) is a N-methylated product of the amino acid glycine. It is 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 meaning it does not meet the definition of a vitamin. It is used in comparative analysis with other N-methylated glycines. N,N-Dimethylglycine is used in the development of glycine-based ionic liquids and emulsifiers, and as a substrate to identify, differentiate and characterize amino acid methyltransferase(s). It is potentially useful as a biomarker of protein degradation in COPD patients.

History

N,N-Dimethylglycine was discovered in 1943. It is found in some but not all formulations of pangamic acid (vitamin B15). Pangamic acid has been sold as a dietary supplement in the United States at least since the late 1970s, when the lay press celebrated its benefits. Although pangamic acid is also known as vitamin B16, it is not actually a vitamin because no deficiency state has been identified, and it has no known nutritional value.

Uses

N,N-Dimethylglycine is used as an athletic performance enhancer and immunostimulant. It is also used in the treatment of autism, epilepsy and mitochondrial disease. It is also employed as a biomarker of protein degradation in chronic obstructive lung disease (COPD) patients. Further, it is used as a substrate to identify, differentiate and characterize amino acid methyltransferase. It plays an important role for the development of glycine-based ionic liquids and emulsifiers.

General Description

N,N-Dimethylglycine is a type of quaternary ammonium compound which exhibits a variety of biological effects.

Preparation & Synthesis

Preparation

N,N-Dimethylglycine 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. H2NCH2COOH + 2 CH2O + 2 HCOOH →(CH3)2NCH2COOH + 2 CO2 + 2 H2O.