Compound: sarcosine
SMILES: O=C(O)CNC
InChIKey: FSYKKLYZXJSNPZ-UHFFFAOYSA-N
Synonyms: sarcosine, 107-97-1, N-methylglycine, 2-(methylamino)acetic acid, Sarcosinic acid, Methylaminoacetic acid, N-Methylaminoacetic acid, Methylglycine, Glycine, N-methyl-, (Methylamino)acetic acid, Sarcosin, (Methylamino)ethanoic acid, Acetic acid, (methylamino)-, (methylamino)acetate, CHEBI:15611, Methylaminoethanoic acid, Z711V88R5F, DTXSID1047025, N Methylglycine, Sarcosylate, Magnesium, METHYL GLYCOCOLL, RefChem:181358, DTXCID9027025, 203-538-6, 2-(methylazaniumyl)acetate, Sargosine hydrochloride, N-Methyl glycine, N-Methylglycocoll, N-methyl-Glycine, MFCD00004279, BRN 1699442, 25951-24-0, SAR, AI3-15410, Methylamino-Acetic Acid, CHEMBL304383, Cocoylsarcosine, 2-Methylaminoethanoic acid, Cocobetaine, Cocoyl sarcosine, SMR000857358, N-Cocoyl-N-methylglycine, EINECS 203-538-6, arcosine, methyl-glycine, UNII-820Q60DZ0I, UNII-Z711V88R5F, L-sarcosine, MeGly, N-Cocoyl sarcosine, N-Methyl-glycocoll, Sarcosine, BioXtra, EINECS 270-156-4, N-Methylaminoacetate, Sarcosine, 98%, Me-Gly-OH, MeNHCH2COOH, (methylamino)-Acetate, NSC 118114, (Methylamino)ethanoate, CH3NHCH2COOH, SARCOSINE [MI], CH3NHCH2CO2H, acetic acid, methylamino-, (methylamino)-Acetic acid, SCHEMBL149, N-Cocoyl-N-methyl glycine, bmse000160, Epitope ID:969157, SARCOSINE [WHO-DD], MLS001335909, MLS001335910, SCHEMBL742517, GTPL4713, orb1300297, orb3141435, SCHEMBL1316815, SCHEMBL5254283, SCHEMBL5884235, SCHEMBL27340032, 25951-24-0(free base), MSK1477, Sarcosine, >=99.0% (NT), 820Q60DZ0I, HMS2231J19, STR01554, AC7804, BBL009707, BDBM50017225, EBC-03031, NSC118114, s4702, STL141072, AKOS000120139, CCG-266018, CS-W018511, DB12519, FS02744, NSC-118114, Sarcosine(Discontinued,SeeCPTD788386), BP-12554, DA-57664, Sarcosine, crystallized, >=98.0% (T), SY001630, HY-101037, M0332, NS00004104, EN300-20732, Glycine Impurity 6Glycine EP Impurity F HCI, C00213, F095119, Q414157, 2-(Methylamino)Acetic Acid; Glycine EP Impurity F, W-108729, 2-Methylaminoethanoic acid; N-Methylglycine; H-Sar-OH, BRD-K51263939-001-08-6, F0001-0147, Z104480276, 484652ED-E55A-4308-8F42-0903E08DBAF4, InChI=1/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6
Theoretical properties:
molecular_formula: C3H7NO2
molecular_weight: 89.09 g/mol
exact_mass: 89.047678466 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 2
heavy_atom_count: 6
topological_polar_surface_area: 49.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 406 °F (Decomposes) (NTP, 1992)
solubility: greater than or equal to 100 mg/mL at 61 °F (NTP, 1992)
vapor_pressure: 0.00000017 [mmHg]
Descriptions:
pubchem: Sarcosine is a N-alkylglycine that is the N-methyl derivative of glycine. It is an intermediate in the metabolic pathway of glycine. It has a role as a glycine transporter 1 inhibitor, a glycine receptor agonist, a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is a N-methyl-amino acid, a member of N-methylglycines and a N-alkylglycine. It is a conjugate base of a sarcosinium. It is a conjugate acid of a sarcosinate. It is a tautomer of a sarcosine zwitterion.
chebi: A <em>N</em>-alkylglycine that is the <em>N</em>-methyl derivative of glycine. It is an intermediate in the metabolic pathway of glycine.
chembl: SARCOSINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: 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.