CHEBI:15611 - sarcosine

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ChEBI Name sarcosine
ChEBI ID CHEBI:15611
Definition A N-alkylglycine that is the N-methyl derivative of glycine. It is an intermediate in the metabolic pathway of glycine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45442, CHEBI:45531, CHEBI:45614, CHEBI:45381, CHEBI:10876, CHEBI:12609, CHEBI:9029, CHEBI:15065, CHEBI:21765
Supplier Information ChemicalBook:CB9712144, eMolecules:480611, ZINC000004658561
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Sarcosine, also known as N-methylglycine, or monomethylglycine, is a amino acid with the formula CH3N(H)CH2CO2H. It exists at neutral pH as the zwitterion CH3N+(H)2CH2CO2−, which can be obtained as a white, water-soluble powder. Like some amino acids, sarcosine converts to a cation at low pH and an anion at high pH, with the respective formulas CH3N+(H)2CH2CO2H and CH3N(H)CH2CO2−. Sarcosine is a close relative of glycine, with a secondary amine in place of the primary amine. 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. Sarcosine is sweet to the taste.
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Formula C3H7NO2
Net Charge 0
Average Mass 89.09322
Monoisotopic Mass 89.04768
InChI InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)
InChIKey FSYKKLYZXJSNPZ-UHFFFAOYSA-N
SMILES CNCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
glycine transporter 1 inhibitor
Any glycine transporter inhibitor that interferes with the action of glycine 1 transporters.
glycine receptor agonist
An agonist that binds to and activates glycine receptors
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sarcosine (CHEBI:15611) has role Escherichia coli metabolite (CHEBI:76971)
sarcosine (CHEBI:15611) has role glycine receptor agonist (CHEBI:64589)
sarcosine (CHEBI:15611) has role glycine transporter 1 inhibitor (CHEBI:64588)
sarcosine (CHEBI:15611) has role human metabolite (CHEBI:77746)
sarcosine (CHEBI:15611) has role mouse metabolite (CHEBI:75771)
sarcosine (CHEBI:15611) is a N-alkylglycine (CHEBI:66933)
sarcosine (CHEBI:15611) is a N-methyl-amino acid (CHEBI:21760)
sarcosine (CHEBI:15611) is a N-methylglycines (CHEBI:21766)
sarcosine (CHEBI:15611) is conjugate acid of sarcosinate (CHEBI:46915)
sarcosine (CHEBI:15611) is conjugate base of sarcosinium (CHEBI:46842)
sarcosine (CHEBI:15611) is tautomer of sarcosine zwitterion (CHEBI:57433)
Incoming N-nitrososarcosine (CHEBI:82363) has functional parent sarcosine (CHEBI:15611)
sarcosinium (CHEBI:46842) is conjugate acid of sarcosine (CHEBI:15611)
sarcosinate (CHEBI:46915) is conjugate base of sarcosine (CHEBI:15611)
sarcosine zwitterion (CHEBI:57433) is tautomer of sarcosine (CHEBI:15611)
IUPAC Name
sarcosine
Synonyms Sources
(methylamino)acetic acid ChemIDplus
(methylamino)ethanoic acid NIST Chemistry WebBook
L-sarcosine
Note: (2015-03-26) A misnomer which has been frequently used in the primary literature - sarcosine does not have a chiral centre, so cannot be either D or L.
ChEBI
MeGly ChEBI
methylaminoacetic acid NIST Chemistry WebBook
N-methylaminoacetic acid NIST Chemistry WebBook
N-Methylglycine KEGG COMPOUND
Sar IUPAC
Sarcosine KEGG COMPOUND
SARCOSINE PDBeChem
sarcosinic acid ChemIDplus
Manual Xrefs Databases
C00213 KEGG COMPOUND
c0135 UM-BBD
HMDB0000271 HMDB
SAR PDBeChem
Sarcosine Wikipedia
SARCOSINE MetaCyc
View more database links
Registry Numbers Types Sources
107-97-1 CAS Registry Number NIST Chemistry WebBook
107-97-1 CAS Registry Number ChemIDplus
1699442 Reaxys Registry Number Reaxys
2018 Gmelin Registry Number Gmelin
Citations
Yang SY, Hong CJ, Huang YH, Tsai SJ (2010)
The effects of glycine transporter I inhibitor, N-methylglycine (sarcosine), on ketamine-induced alterations in sensorimotor gating and regional brain c-Fos expression in rats.
Neuroscience letters 469, 127-130 [PubMed:19944746]
[show Abstract]
Zhang HX, Lyons-Warren A, Thio LL (2009)
The glycine transport inhibitor sarcosine is an inhibitory glycine receptor agonist.
Neuropharmacology 57, 551-555 [PubMed:19619564]
[show Abstract]
Centeno MV, Mutso A, Millecamps M, Apkarian AV (2009)
Prefrontal cortex and spinal cord mediated anti-neuropathy and analgesia induced by sarcosine, a glycine-T1 transporter inhibitor.
Pain 145, 176-183 [PubMed:19577367]
[show Abstract]
Zhang HX, Hyrc K, Thio LL (2009)
The glycine transport inhibitor sarcosine is an NMDA receptor co-agonist that differs from glycine.
The Journal of physiology 587, 3207-3220 [PubMed:19433577]
[show Abstract]
Shim SS, Hammonds MD, Kee BS (2008)
Potentiation of the NMDA receptor in the treatment of schizophrenia: focused on the glycine site.
European archives of psychiatry and clinical neuroscience 258, 16-27 [PubMed:17901997]
[show Abstract]
Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL (2007)
A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human.
Physiological genomics 29, 99-108 [PubMed:17190852]
[show Abstract]
Tsai GE, Yang P, Chang YC, Chong MY (2006)
D-alanine added to antipsychotics for the treatment of schizophrenia.
Biological psychiatry 59, 230-234 [PubMed:16154544]
[show Abstract]
Deutsch SI, Rosse RB, Long KD, Gaskins B, Mastropaolo J (2006)
Rare neurodevelopmental abnormalities of sarcosinemia may involve glycinergic stimulation of a primed N-methyl-d-aspartate receptor.
Clinical neuropharmacology 29, 361-363 [PubMed:17095900]
[show Abstract]
Tsai G, Lane HY, Yang P, Chong MY, Lange N (2004)
Glycine transporter I inhibitor, N-methylglycine (sarcosine), added to antipsychotics for the treatment of schizophrenia.
Biological psychiatry 55, 452-456 [PubMed:15023571]
[show Abstract]
Huang H, Barakat L, Wang D, Bordey A (2004)
Bergmann glial GlyT1 mediates glycine uptake and release in mouse cerebellar slices.
The Journal of physiology 560, 721-736 [PubMed:15331688]
[show Abstract]
Mori M, Gähwiler BH, Gerber U (2002)
Beta-alanine and taurine as endogenous agonists at glycine receptors in rat hippocampus in vitro.
The Journal of physiology 539, 191-200 [PubMed:11850512]
[show Abstract]
Gederaas OA, Holroyd A, Brown SB, Vernon D, Moan J, Berg K (2001)
5-Aminolaevulinic acid methyl ester transport on amino acid carriers in a human colon adenocarcinoma cell line.
Photochemistry and photobiology 73, 164-169 [PubMed:11272730]
[show Abstract]
Last Modified
27 January 2016