CHEBI:6872 - methylene blue

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ChEBI Name methylene blue
ChEBI ID CHEBI:6872
Definition An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C16H18N3S.Cl
Net Charge 0
Average Mass 319.85200
Monoisotopic Mass 319.091
InChI InChI=1S/C16H18N3S.ClH/c1-18(2)11-5-7-13-15(9-11)20-16-10-12(19(3)4)6-8-14(16)17-13;/h5-10H,1-4H3;1H/q+1;/p-1
InChIKey CXKWCBBOMKCUKX-UHFFFAOYSA-M
SMILES [Cl-].CN(C)c1ccc2nc3ccc(cc3[s+]c2c1)N(C)C
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): EC 1.4.3.4 (monoamine oxidase) inhibitor
An EC 1.4.3.* (oxidoreductase acting on donor CH-NH2 group, oxygen as acceptor) inhibitor that interferes with the action of monoamine oxidase (EC 1.4.3.4).
EC 3.1.1.8 (cholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
EC 4.6.1.2 (guanylate cyclase) inhibitor
An EC 4.6.* (P1O lyase) inhibitor that interferes with the action of enzyme guanylate cyclase (EC 4.6.1.2).
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
Application(s): acid-base indicator
An acid or base which exhibits a colour change on neutralization by the basic or acidic titrant at or near the equivalence point of a titration.
fluorochrome
A fluorescent dye used to stain biological specimens.
antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
histological dye
A dye used in microscopic or electron microscopic examination of cells and tissues to give contrast and to highlight particular features of interest, such as nuclei and cytoplasm.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
physical tracer
A physical tracer is one that is attached by physical means to the object being traced.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing methylene blue (CHEBI:6872) has part 3,7-bis(dimethylamino)phenothiazin-5-ium (CHEBI:43830)
methylene blue (CHEBI:6872) has role acid-base indicator (CHEBI:50407)
methylene blue (CHEBI:6872) has role antidepressant (CHEBI:35469)
methylene blue (CHEBI:6872) has role antimalarial (CHEBI:38068)
methylene blue (CHEBI:6872) has role antimicrobial agent (CHEBI:33281)
methylene blue (CHEBI:6872) has role antioxidant (CHEBI:22586)
methylene blue (CHEBI:6872) has role cardioprotective agent (CHEBI:77307)
methylene blue (CHEBI:6872) has role EC 1.4.3.4 (monoamine oxidase) inhibitor (CHEBI:38623)
methylene blue (CHEBI:6872) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
methylene blue (CHEBI:6872) has role EC 4.6.1.2 (guanylate cyclase) inhibitor (CHEBI:78678)
methylene blue (CHEBI:6872) has role fluorochrome (CHEBI:51217)
methylene blue (CHEBI:6872) has role histological dye (CHEBI:77178)
methylene blue (CHEBI:6872) has role neuroprotective agent (CHEBI:63726)
methylene blue (CHEBI:6872) has role physical tracer (CHEBI:35208)
methylene blue (CHEBI:6872) is a organic chloride salt (CHEBI:36094)
IUPAC Name
3,7-bis(dimethylamino)phenothiazin-5-ium chloride
INNs Sources
chlorure de méthylthioninium ChemIDplus
cloruro de metiltioninio ChemIDplus
methylthioninii chloridum ChemIDplus
methylthioninium chloride ChemIDplus
Synonyms Sources
azul de metileno ChEBI
Basic Blue 9 ChemIDplus
bleu de méthylène ChemIDplus
C.I. 52015 ChEBI
Methylenblau ChemIDplus
Methylene blue KEGG COMPOUND
Methylene Blue anhydrous ChemIDplus
Methylthioninium chloride KEGG COMPOUND
Solvent blue 8 ChEBI
Swiss blue ChEBI
Database Links Databases
C00220 KEGG COMPOUND
Methylene_blue Wikipedia
View more database links
Registry Numbers Types Sources
3599847 Reaxys Registry Number Reaxys
3599847 Beilstein Registry Number Beilstein
61-73-4 CAS Registry Number ChemIDplus
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Last Modified
24 November 2015