Sarcosine
| Names | |
|---|---|
| IUPAC name
N-Methylglycine
| |
| Systematic IUPAC name
(Methylamino)acetic acid | |
| Identifiers | |
3D model (JSmol)
|
|
| 1699442 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.217 |
| EC Number |
|
| 2018 | |
| KEGG | |
| MeSH | Sarcosine |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
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| Properties | |
| C3H7NO2 | |
| Molar mass | 89.094 g·mol−1 |
| Appearance | White solid |
| Odor | Odourless |
| Density | 1.093 g/mL |
| Melting point | 208 to 212 °C (406 to 414 °F; 481 to 485 K) experimental |
| 89.09 g L−1 (at 20 °C) | |
| log P | 0.599 |
| Acidity (pKa) | 2.36 |
| Basicity (pKb) | 11.64 |
| UV-vis (λmax) | 260 nm |
| Absorbance | 0.05 |
| Thermochemistry | |
Heat capacity (C)
|
128.9 J K−1 mol−1 |
Std enthalpy of
formation (ΔfH⦵298) |
−513.50–−512.98 kJ mol−1 |
Std enthalpy of
combustion (ΔcH⦵298) |
−1667.84–−1667.54 kJ mol−1 |
| Related compounds | |
Related alkanoic acids
|
|
Related compounds
|
Dimethylacetamide |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
| |
Sarcosine, also known as N-methylglycine, or monomethylglycine, is a non-proteinogenic amino acid with the formula CH3N(H)CH2CO2H. It is the N-methyl derivative of glycine, with a secondary amine in place of the primary amine, and occurs naturally in muscles and other body tissues as an intermediate in the metabolism of choline to glycine. It was first isolated and named by the German chemist Justus von Liebig in 1847.
Sarcosine is ubiquitous in biological materials. It is used in manufacturing biodegradable surfactants and toothpastes as well as in other applications. It is also a reagent in organic synthesis. It has a mildly sweet taste.
Pharmacologically, sarcosine functions as a competitive inhibitor of the glycine transporter type 1 (GlyT1), a co-agonist at the glycine binding site of the NMDA receptor, and, at higher concentrations, an agonist at the strychnine-sensitive glycine receptor. These properties have led to its investigation as an adjunctive treatment in schizophrenia and major depressive disorder. Sarcosine has also been identified as an oncometabolite in prostate cancer, where elevated levels correlate with disease progression and metastatic potential.