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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 perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
unspecified [Ki 1900 uM]
yes [IC50 91 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Analysis of amino acids as formamidene butyl esters by electrospray ionization tandem mass spectrometry.
2001
ICE bioassay. Isolating in vivo complexes of enzyme to DNA.
2001
Intracellular re-routing of prion protein prevents propagation of PrP(Sc) and delays onset of prion disease.
2001 Aug 1
Investigations into biochemical changes due to diurnal variation and estrus cycle in female rats using high-resolution (1)H NMR spectroscopy of urine and pattern recognition.
2001 Aug 15
Osmolytes stabilize ribonuclease S by stabilizing its fragments S protein and S peptide to compact folding-competent states.
2001 Aug 3
N[3-(4'-fluorophenyl)-3-(4'-phenylphenoxy)propyl]sarcosine (NFPS) is a selective persistent inhibitor of glycine transport.
2001 Dec
Ultrastructural and biochemical localization of N-RAP at the interface between myofibrils and intercalated disks in the mouse heart.
2001 Dec 11
The Gd(3+) complex of a fatty acid analogue of DOTP binds to multiple albumin sites with variable water relaxivities.
2001 Dec 17
5-Aminolaevulinic acid methyl ester transport on amino acid carriers in a human colon adenocarcinoma cell line.
2001 Feb
N-methyltryptophan oxidase from Escherichia coli: reaction kinetics with N-methyl amino acid and carbinolamine substrates.
2001 Feb 6
Characterization of the FAD-containing N-methyltryptophan oxidase from Escherichia coli.
2001 Feb 6
Organization of the genes involved in dimethylglycine and sarcosine degradation in Arthrobacter spp.: implications for glycine betaine catabolism.
2001 Jun
Analysis of alcohols, as dimethylglycine esters, by electrospray ionization tandem mass spectrometry.
2001 Mar
Expression profiling of cardiac genes in human hypertrophic cardiomyopathy: insight into the pathogenesis of phenotypes.
2001 Oct
Amperometric creatinine biosensor for hemodialysis patients.
2001 Oct
Monomeric sarcosine oxidase: evidence for an ionizable group in the E.S complex.
2002 Aug 6
Efficacy of macromolecular crowding in forcing proteins to fold.
2002 Dec 10
Biosensors and flow-through system for the determination of creatinine in hemodialysate.
2002 Jan
Cofactors in sarcosine oxidase from Corynebacterium sp. U-96.
2002 Jan
Polyols induce ATP-independent folding of GroEL-bound bacterial glutamine synthetase.
2002 Jan 15
Ion conductors derived from biogenic amines, bile acids, and amino acids.
2002 Nov-Dec
Promoter escape by RNA polymerase II.
2002 Sep 13
Optimized conventional synthesis of "RGD" and "RGDS" peptides and their sarcosine mimics as integrin GP IIb/IIIa antagonists.
2003 Jun
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 Fri Dec 15 14:57:53 UTC 2023
Edited
by admin
on Fri Dec 15 14:57:53 UTC 2023
Record UNII
Z711V88R5F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SARCOSINE
INCI   MI   WHO-DD  
INCI  
Official Name English
METHYLAMINOETHANOIC ACID
Systematic Name English
N-METHYLGLYCINE
Systematic Name English
N-METHYLAMINOACETIC ACID
Systematic Name English
SARCOSINE [INCI]
Common Name English
SARCOSINE [MI]
Common Name English
SAR
Common Name English
Sarcosine [WHO-DD]
Common Name English
Classification Tree Code System Code
LOINC 26724-5
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 25133-0
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 2930-6
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 28610-4
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 9323-7
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 44401-8
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 17568-7
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 2931-4
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 26598-3
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
DSLD 1956 (Number of products:3)
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
FDA ORPHAN DRUG 346611
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 25978-8
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 13380-1
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 53150-9
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 13806-5
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
NCI_THESAURUS C231
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 26613-0
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 26932-4
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 13413-0
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 2932-2
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
LOINC 25518-2
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
Code System Code Type Description
PUBCHEM
1088
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
RXCUI
1370611
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
NCI_THESAURUS
C113501
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
MESH
D012521
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
FDA UNII
Z711V88R5F
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
ECHA (EC/EINECS)
203-538-6
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
CHEBI
57433
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
DAILYMED
Z711V88R5F
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
WIKIPEDIA
SARCOSINE
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
DRUG BANK
DB12519
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
EPA CompTox
DTXSID1047025
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
RXCUI
1362906
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY RxNorm
MERCK INDEX
m9780
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY Merck Index
CAS
107-97-1
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
CHEBI
46915
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
SMS_ID
100000078397
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
EVMPD
SUB15197MIG
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
CHEBI
15611
Created by admin on Fri Dec 15 14:57:53 UTC 2023 , Edited by admin on Fri Dec 15 14:57:53 UTC 2023
PRIMARY
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SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY