N,N-Dimethylglycine
DMG · DIMETHYLGLYCINE · n-methylsarcosine · (DIMETHYLAMINO)ACETIC ACID · N-Me-Sar-OH · AKOS BB-5614 · N-DiMethylglycine · N,N-Dimthylglycine
식별자 및 물리적 특성
| CAS No. | 1118-68-9 |
|---|---|
| 분자식 | C4H9NO2 |
| 평균 분자량 | 103.12 g/mol |
| 단동위원소 질량 | 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 |
화학 및 물리적 성질
| XLogP | -2.9 |
|---|---|
| 극성 표면적 | 40.5 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 7 |
| 형식 전하 | 0 |
| 복잡도 | 70 |
| LogP(분배 계수) | -2.91 |
| 끓는 점 | 63.9193.35°C (rough estimate) |
| 녹는점 | 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]+ |
| 밀도 | 1 g/cm3 |
| 굴절률 | 1.4674 (estimate) |
| 저장 조건 | Keep in dark place,Sealed in dry,Room Temperature |
| 용해도 | 메탄올(약간 용해됨), 물(약간 용해됨) |
| pKa(산도 계수) | 9.89(at 25℃) |
| 물리적 상태 | 결정성 분말 |
| 색상 | 흰색에서 약간 노란색 |
| 용해도 | 녹는 |
| 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 |
| EPA | Glycine, N,N-dimethyl- (1118-68-9) |
화학적 성질
white to slightly yellow crystalline powder
안전 및 규제
| GHS 분류 | 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. |
|---|---|
| 규제 정보 | 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%) |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | MB9865000 |
| 독성 | 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. |
| 관세 코드 | 29224999 |
| 위험 문구(R) | 22-36/37/38 |
| 위험 표시 | Xn,Xi |
| 안전 문구(S) | 24/25-36/37-26 |
| 위험 등급 | IRRITANT |
| 기존화학 물질 | KE-11416 |
| F 고인화성물질 | 3 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
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.
역사
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.
용도
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.
일반 설명
N,N-Dimethylglycine is a type of quaternary ammonium compound which exhibits a variety of biological effects.
제조 및 합성 방법
제조 방법
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.