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
SMILES
CNCC(O)=O
InChI
InChIKey=FSYKKLYZXJSNPZ-UHFFFAOYSA-N
InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)
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
Sources: http://www.supersmart.com/en--Neuro-Nutrition--Sarcosine-500-mg--0687 | https://www.ncbi.nlm.nih.gov/pubmed/23880848
Curator's Comment: Sarcosine was first isolated and named by the German chemist Justus von Liebig in 1847
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3392921 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19619564 |
3.2 mM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25841105/ |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
unspecified [Ki 1900 uM] | ||||
yes [IC50 91 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.uniprot.org/uniprot/Q9P0Z9 |
yes | |||
Sources: https://www.uniprot.org/uniprot/Q9UL12 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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Intracellular re-routing of prion protein prevents propagation of PrP(Sc) and delays onset of prion disease. | 2001 Aug 1 |
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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 |
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Osmolytes stabilize ribonuclease S by stabilizing its fragments S protein and S peptide to compact folding-competent states. | 2001 Aug 3 |
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N[3-(4'-fluorophenyl)-3-(4'-phenylphenoxy)propyl]sarcosine (NFPS) is a selective persistent inhibitor of glycine transport. | 2001 Dec |
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Ultrastructural and biochemical localization of N-RAP at the interface between myofibrils and intercalated disks in the mouse heart. | 2001 Dec 11 |
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The Gd(3+) complex of a fatty acid analogue of DOTP binds to multiple albumin sites with variable water relaxivities. | 2001 Dec 17 |
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5-Aminolaevulinic acid methyl ester transport on amino acid carriers in a human colon adenocarcinoma cell line. | 2001 Feb |
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N-methyltryptophan oxidase from Escherichia coli: reaction kinetics with N-methyl amino acid and carbinolamine substrates. | 2001 Feb 6 |
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Characterization of the FAD-containing N-methyltryptophan oxidase from Escherichia coli. | 2001 Feb 6 |
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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
Sources: https://examine.com/supplements/sarcosine/
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12667895
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
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admin
on
Edited
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Record UNII |
Z711V88R5F
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Record Status |
Validated (UNII)
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Record Version |
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |