N,N-Dimethylglycin
DMG · DIMETHYLGLYCINE · n-methylsarcosine · (DIMETHYLAMINO)ACETIC ACID · N-Me-Sar-OH · AKOS BB-5614 · N-DiMethylglycine · N,N-Dimthylglycine
Identifikatoren & physikalische Daten
| CAS No. | 1118-68-9 |
|---|---|
| Summenformel | C4H9NO2 |
| Durchschnittliche Molmasse | 103,12 g/mol |
| Monoisotopische Masse | 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 |
| Lokaler Name | N,N-Dimethylglycin |
Chemische & physikalische Eigenschaften
| XLogP | -2,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 40,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 70 |
| LogP (Verteilungskoeffizient) | -2.91 |
| Siedepunkt | 63.9193.35°C (rough estimate) |
| Schmelzpunkt | 185.5185.5 °C178-182 °C(lit.) |
| Physical Description | Solid |
| Dissociation Constants | 2.04 |
| Collision Cross Section | 119.7 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]116 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine]123.1 Ų [M+H]+ |
| Dichte | 1 g/cm3 |
| Brechungsindex | 1.4674 (estimate) |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| Löslichkeit | Methanol (Slightly), Water (Slightly)soluble |
| pKa (Säurekonstante) | 9.89(at 25℃) |
| Aggregatzustand | Crystalline Powder |
| Farbe | White to slightly yellow |
| 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 Datenbank | 1118-68-9(CAS DataBase Reference) |
| EPA chemische Informationen | Glycine, N,N-dimethyl- (1118-68-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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. |
|---|---|
| Regulatorische Informationen | 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 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29224999 |
| RTECS-Nr. | MB9865000 |
| R-Sätze (R) | 22-36/37/38 |
| Toxizität | 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. |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 24/25-36/37-26 |
| Gefahrenklasse | IRRITANT |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
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.
Herstellung & Synthese
synthetische
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.