N,N-ジメチルグリシン
N,N-ジメチルグリシン · ジメチルアミノ酢酸 · ジメチルグリシン · (ジメチルアミノ)酢酸 · N,N-ジメチルアミノ酢酸 · N,N‐ジメチルグリシン · N,N-ジメチルグリシン, フリーベース · N,N-ジメチルグリシン, フリーベース, 99%
識別子と物理属性
| CAS No. | 1118-68-9 |
|---|---|
| 分子式 | C4H9NO2 |
| 平均分子量 | 103.12 g/mol |
| 単同位体質量 | 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 |
| 現地名 | N,N-ジメチルグリシン |
化学・物理的性質
| XLogP | -2.9 |
|---|---|
| 極性表面積 | 40.5 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 2 |
| 重原子数 | 7 |
| 形式電荷 | 0 |
| 複雑度 | 70 |
| LogP（分配係数） | -2.91 |
| 沸点 | 63.9193.35°C (rough estimate) |
| 融点 | 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]+ |
| 密度 | 1 g/cm3 |
| 屈折率 | 1.4674 (estimate) |
| 貯蔵条件 | Keep in dark place,Sealed in dry,Room Temperature |
| 溶解度 | メタノール（微量）、水（微量）溶ける |
| pKa（酸解離定数） | 9.89(at 25℃) |
| 外観・状態 | 結晶性粉末 |
| 色 | 白色～やや黄色 |
| 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 データベース | 1118-68-9(CAS DataBase Reference) |
| EPAの化学物質情報 | Glycine, N,N-dimethyl- (1118-68-9) |
化学的特性
white to slightly yellow crystalline powder
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | 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 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | MB9865000 |
| 毒性 | 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. |
| 税関コード | 29224999 |
| 危険文句（R） | 22-36/37/38 |
| 危険表示 | Xn,Xi |
| 安全措置（S） | 24/25-36/37-26 |
| 危険等級 | IRRITANT |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
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.
来歴
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.
使用
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.
一般的な説明
N,N-Dimethylglycine is a type of quaternary ammonium compound which exhibits a variety of biological effects.
製法・合成法
製造方法
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.