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Details

Stereochemistry ACHIRAL
Molecular Formula C3H7NO2
Molecular Weight 89.0932
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SARCOSINE

SMILES

CNCC(O)=O

InChI

InChIKey=FSYKKLYZXJSNPZ-UHFFFAOYSA-N
InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)

HIDE SMILES / InChI

Molecular Formula C3H7NO2
Molecular Weight 89.0932
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Sarcosine, also known as N-methylglycine, is a metabolite of glycine. It shares properties with both glycine and D-serine, though its effects are weaker. Sarcosine supplementation can be used to alleviate symptoms of depression and schizophrenia, or improve cognition. It is absorbed more reliably by the body than D-serine, which can also treat similar conditions. Sarcosine is being investigated for its connection to prostate cancer. It may be a biomarker for prostate cancer, which means that if sarcosine levels in the blood are higher than normal, it could be an indicator of prostate cancer. This doesn’t mean that sarcosine itself causes cancer. More research is needed to confirm this relationship. Sarcosine’s main mechanism involves inhibiting a transporter, called GlyT1, which takes up glycine and D-serine into cells. This increases the levels of glycine and D-serine in the body and increases their effects. Sarcosine, a glycine transporter type 1 inhibitor and an N-methyl-D-aspartate (NMDA) receptor co-agonist at the glycine binding site, potentiates NMDA receptor function. Sarcosine is an inhibitory glycine receptor agonist.

Originator

Curator's Comment: Sarcosine was first isolated and named by the German chemist Justus von Liebig in 1847

Approval Year

T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1 h
4 g 1 times / day multiple, oral
dose: 4 g
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SARCOSINE serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 1900 uM]
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Okadaic acid-induced, naringin-sensitive phosphorylation of glycine N-methyltransferase in isolated rat hepatocytes.
2003-07-15
New N-RAP-binding partners alpha-actinin, filamin and Krp1 detected by yeast two-hybrid screening: implications for myofibril assembly.
2003-06-01
Optimized conventional synthesis of "RGD" and "RGDS" peptides and their sarcosine mimics as integrin GP IIb/IIIa antagonists.
2003-06
Sarcosine-maleic acid (1:1) crystal: structure, 13C NMR and vibrational properties, protonation character.
2003-06
Modeling anhydrous and aqua copper(II) amino acid complexes: a new molecular mechanics force field parametrization based on quantum chemical studies and experimental crystal data.
2003-04-07
[3H]-(R)-NPTS, a radioligand for the type 1 glycine transporter.
2003-04-07
Kinetic mechanisms of glycine oxidase from Bacillus subtilis.
2003-04
Role of EphA4 and EphrinB3 in local neuronal circuits that control walking.
2003-03-21
Structural and mechanistic studies on ThiO, a glycine oxidase essential for thiamin biosynthesis in Bacillus subtilis.
2003-03-18
The glycine transporter-1 inhibitors NFPS and Org 24461: a pharmacological study.
2003-03
Oral bile acids reduce bacterial overgrowth, bacterial translocation, and endotoxemia in cirrhotic rats.
2003-03
A hydrophobicity scale for the lipid bilayer barrier domain from peptide permeabilities: nonadditivities in residue contributions.
2003-02-18
Isolation and functional characterization of N-methyltransferases that catalyze betaine synthesis from glycine in a halotolerant photosynthetic organism Aphanothece halophytica.
2003-02-14
Synthesis, antimicrobial and antifungal activity of a new class of spiro pyrrolidines.
2003-02-06
Tautomeric rearrangement of a dihydroflavin bound to monomeric sarcosine oxidase or N-methyltryptophan oxidase.
2003-02-04
Microfabricated electrophoresis chip for bioassay of renal markers.
2003-02-01
Glycine tranporter-1 blockade potentiates NMDA-mediated responses in rat prefrontal cortical neurons in vitro and in vivo.
2003-02
Determination of choline, betaine, and dimethylglycine in plasma by a high-throughput method based on normal-phase chromatography-tandem mass spectrometry.
2003-02
Pt(II) and Pd(II) derivatives of ter-butylsarcosinedithiocarbamate. Synthesis, chemical and biological characterization and in vitro nephrotoxicity.
2003-01-15
Pharmacokinetics of oral betaine in healthy subjects and patients with homocystinuria.
2003-01
The effect of short-term dimethylglycine treatment on oxygen consumption in cytochrome oxidase deficiency: a double-blind randomized crossover clinical trial.
2003-01
Conjugated bile acid replacement therapy reduces urinary oxalate excretion in short bowel syndrome.
2003-01
Molecular characterization of NikD, a new flavoenzyme important in the biosynthesis of nikkomycin antibiotics.
2002-12-31
Efficacy of macromolecular crowding in forcing proteins to fold.
2002-12-10
Simultaneous horizontal gene transfer of a gene coding for ribosomal protein l27 and operational genes in Arthrobacter sp.
2002-12
Assembly of tau in transgenic animals expressing P301L tau: alteration of phosphorylation and solubility.
2002-12
Ion conductors derived from biogenic amines, bile acids, and amino acids.
2002-11-21
Hydrophobicity and helicity of membrane-interactive peptides containing peptoid residues.
2002-11-15
Abundant tau filaments and nonapoptotic neurodegeneration in transgenic mice expressing human P301S tau protein.
2002-11-01
Glycine receptors and transporters on bullfrog retinal Müller cells.
2002-09-16
Promoter escape by RNA polymerase II.
2002-09-13
Iron (III) induces aggregation of hyperphosphorylated tau and its reduction to iron (II) reverses the aggregation: implications in the formation of neurofibrillary tangles of Alzheimer's disease.
2002-09
Synthesis, characterization and in vitro cytotoxicity of new organotin(IV) derivatives of N-methylglycine.
2002-08-15
Monomeric sarcosine oxidase: role of histidine 269 in catalysis.
2002-08-06
Monomeric sarcosine oxidase: evidence for an ionizable group in the E.S complex.
2002-08-06
Argyrins, immunosuppressive cyclic peptides from myxobacteria. II. Structure elucidation and stereochemistry.
2002-08
Elevated plasma total homocysteine in severe methionine adenosyltransferase I/III deficiency.
2002-08
A new conceptual framework for enzyme catalysis. Hydrogen tunnelling coupled to enzyme dynamics in flavoprotein and quinoprotein enzymes.
2002-07
Assay of the concentration and (13)C isotopic enrichment of propionyl-CoA, methylmalonyl-CoA, and succinyl-CoA by gas chromatography-mass spectrometry.
2002-06-01
1H and (13)C NMR spectroscopic analysis of human saliva.
2002-06
Peptoid residues and beta-turn formation.
2002-06
Mechanistic aspects of the covalent flavoprotein dimethylglycine oxidase of Arthrobacter globiformis studied by stopped-flow spectrophotometry.
2002-04-09
An unexpected Diels-Alder reaction on the fullerene core rather than an expected 1,3-dipolar cycloaddition.
2002-04-07
Detergent extract from chlamydial elementary bodies used as antigen for enzyme-linked immunosorbent assay.
2002-04
Late-onset frontotemporal dementia with a novel exon 1 (Arg5His) tau gene mutation.
2002-04
Single crystal EPR studies on Mn(II)-doped sarcosine cadmium chloride and sarcosine cadmium bromide: study of zero-field splitting tensor in iso-structural complexes.
2002-02
Biosensors and flow-through system for the determination of creatinine in hemodialysate.
2002-01
Cofactors in sarcosine oxidase from Corynebacterium sp. U-96.
2002-01
Lysosomotropic N,N- dimethyl alpha-aminoacid N-alkyl esters and their quaternary ammonium salts as plasma membrane and mitochondrial ATPases inhibitors.
2002
Discovery of the factor Xa inhibitor, ZK 807834 (CI-1031).
2001-06
Patents

Sample Use Guides

In Vivo Use Guide
The standard sarcosine dose is 30mg/kg of bodyweight, which correlates to an approximate dosage range of 2,045 – 2,727 mg for people between 150 – 200 lbs.
Route of Administration: Oral
Glycine (0.1 mM) and sarcosine (5 mM) increased [3H]glycine efflux from superfused rat hippocampal slices preloaded with [3H]glycine.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:33:06 GMT 2025
Edited
by admin
on Mon Mar 31 17:33:06 GMT 2025
Record UNII
Z711V88R5F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SARCOSINE
INCI   MI   WHO-DD  
INCI  
Official Name English
SAR
Preferred Name English
METHYLAMINOETHANOIC ACID
Systematic Name English
N-METHYLGLYCINE
Systematic Name English
N-METHYLAMINOACETIC ACID
Systematic Name English
SARCOSINE [MI]
Common Name English
Sarcosine [WHO-DD]
Common Name English
Classification Tree Code System Code
LOINC 26724-5
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
LOINC 25133-0
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LOINC 2930-6
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LOINC 28610-4
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LOINC 9323-7
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LOINC 44401-8
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LOINC 17568-7
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LOINC 2931-4
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LOINC 26598-3
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DSLD 1956 (Number of products:3)
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
FDA ORPHAN DRUG 346611
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LOINC 25978-8
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LOINC 13380-1
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LOINC 53150-9
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LOINC 13806-5
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NCI_THESAURUS C231
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
LOINC 26613-0
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LOINC 26932-4
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LOINC 13413-0
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LOINC 2932-2
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LOINC 25518-2
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Code System Code Type Description
PUBCHEM
1088
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
RXCUI
1370611
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
NCI_THESAURUS
C113501
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
MESH
D012521
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
FDA UNII
Z711V88R5F
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-538-6
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
CHEBI
57433
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
DAILYMED
Z711V88R5F
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
WIKIPEDIA
SARCOSINE
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
DRUG BANK
DB12519
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
EPA CompTox
DTXSID1047025
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
RXCUI
1362906
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m9780
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY Merck Index
CAS
107-97-1
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
CHEBI
46915
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
SMS_ID
100000078397
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
EVMPD
SUB15197MIG
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
CHEBI
15611
Created by admin on Mon Mar 31 17:33:06 GMT 2025 , Edited by admin on Mon Mar 31 17:33:06 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY