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.
Supplier Information ChemicalBook:CB2748858, ChemicalBook:CB1874891, eMolecules:475553, eMolecules:718289
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Methylthioninium chloride, commonly called methylene blue, is a salt used as a dye and as a medication. As a medication, it is mainly used to treat methemoglobinemia by chemically reducing the ferric iron in hemoglobin to ferrous iron. Specifically, it is used to treat methemoglobin levels that are greater than 30% or in which there are symptoms despite oxygen therapy. It has previously been used for treating cyanide poisoning and urinary tract infections, but this use is no longer recommended. Methylene blue is typically given by injection into a vein. Common side effects include headache, nausea, and vomiting. While use during pregnancy may harm the fetus, not using it in methemoglobinemia is likely more dangerous. Methylene blue was first prepared in 1876, by Heinrich Caro. It is on the World Health Organization's List of Essential Medicines.
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Formula C16H18N3S.Cl
Net Charge 0
Average Mass 319.85200
Monoisotopic Mass 319.09100
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
Manual Xrefs Databases
C00220 KEGG COMPOUND
Methylene_blue Wikipedia
View more database links
Registry Numbers Types Sources
3599847 Reaxys Registry Number Reaxys
61-73-4 CAS Registry Number ChemIDplus
Citations
Fang Q, Yan X, Li S, Sun Y, Xu L, Shi Z, Wu M, Lu Y, Dong L, Liu R, Yuan F, Yang SH (2016)
Methylene Blue Ameliorates Ischemia/Reperfusion-Induced Cerebral Edema: An MRI and Transmission Electron Microscope Study.
Acta neurochirurgica. Supplement 121, 227-236 [PubMed:26463954]
[show Abstract]
Makhadmeh GN, Abdul Aziz A, Abdul Razak K (2016)
The efficacy of methylene blue encapsulated in silica nanoparticles compared to naked methylene blue for photodynamic applications.
Artificial cells, nanomedicine, and biotechnology 44, 1018-1022 [PubMed:25707443]
[show Abstract]
Thiele T, Hron G, Kellner S, Wasner C, Westphal A, Warkentin TE, Greinacher A, Selleng K (2016)
Thrombin generation, ProC(®)Global, prothrombin time and activated partial thromboplastin time in thawed plasma stored for seven days and after methylene blue/light pathogen inactivation.
Blood transfusion = Trasfusione del sangue 14, 66-72 [PubMed:26192785]
[show Abstract]
Mohammed N, Grishkewich N, Waeijen HA, Berry RM, Tam KC (2016)
Continuous flow adsorption of methylene blue by cellulose nanocrystal-alginate hydrogel beads in fixed bed columns.
Carbohydrate polymers 136, 1194-1202 [PubMed:26572462]
[show Abstract]
Jang DH, Donovan S, Nelson LS, Bania TC, Hoffman RS, Chu J (2015)
Efficacy of methylene blue in an experimental model of calcium channel blocker-induced shock.
Annals of emergency medicine 65, 410-415 [PubMed:25441767]
[show Abstract]
De Crozals G, Farre C, Sigaud M, Fortgang P, Sanglar C, Chaix C (2015)
Methylene blue phosphoramidite for DNA labelling.
Chemical communications (Cambridge, England) 51, 4458-4461 [PubMed:25679473]
[show Abstract]
Bae J, McNamara LE, Nael MA, Mahdi F, Doerksen RJ, Bidwell GL, Hammer NI, Jo S (2015)
Nitroreductase-triggered activation of a novel caged fluorescent probe obtained from methylene blue.
Chemical communications (Cambridge, England) 51, 12787-12790 [PubMed:26165999]
[show Abstract]
Kumar M, Tamilarasan R, Arthanareeswaran G, Ismail AF (2015)
Optimization of methylene blue using Ca(2+) and Zn(2+) bio-polymer hydrogel beads: A comparative study.
Ecotoxicology and environmental safety 121, 164-173 [PubMed:25913699]
[show Abstract]
Matos J, Montaña R, Rivero E (2015)
Influence of activated carbon upon the photocatalytic degradation of methylene blue under UV-vis irradiation.
Environmental science and pollution research international 22, 784-791 [PubMed:24788930]
[show Abstract]
Zhang CY, Yu HL, Liu SH, Jiang G, Wang YJ (2015)
Effect of lipiodol and methylene blue on the thoracoscopic preoperative positioning.
International journal of clinical and experimental medicine 8, 7569-7576 [PubMed:26221301]
[show Abstract]
Church JT, Posluszny JA, Hemmila M, To KB, Cherry-Bukowiec JR, Waljee J (2015)
Methylene blue for burn-induced vasoplegia: case report and review of literature.
Journal of burn care & research : official publication of the American Burn Association 36, e107-11 [PubMed:25687361]
[show Abstract]
Larson KJ, Wittwer ED, Nicholson WT, Weingarten TN, Price DL, Sprung J (2015)
Myoclonus in patient on fluoxetine after receiving fentanyl and low-dose methylene blue during sentinel lymph node biopsy.
Journal of clinical anesthesia 27, 247-251 [PubMed:25499271]
[show Abstract]
Liu X, Yang Y, Shi X, Li K (2015)
Fast photocatalytic degradation of methylene blue dye using a low-power diode laser.
Journal of hazardous materials 283, 267-275 [PubMed:25285998]
[show Abstract]
Laes JR, Williams DM, Cole JB (2015)
Improvement in Hemodynamics After Methylene Blue Administration in Drug-Induced Vasodilatory Shock: A Case Report.
Journal of medical toxicology : official journal of the American College of Medical Toxicology 11, 460-463 [PubMed:26310944]
[show Abstract]
Miclescu AA, Svahn M, Gordh TE (2015)
Evaluation of the protein biomarkers and the analgesic response to systemic methylene blue in patients with refractory neuropathic pain: a double-blind, controlled study.
Journal of pain research 8, 387-397 [PubMed:26213475]
[show Abstract]
Smith CJ, Wang D, Sgambelluri A, Kramer RS, Gagnon DJ (2015)
Serotonin syndrome following methylene blue administration during cardiothoracic surgery.
Journal of pharmacy practice 28, 207-211 [PubMed:25613051]
[show Abstract]
Shou-wang C, Shi-zhong Y, Wen-ping L, Geng C, Wan-qing G, Wei-dong D, Wei-yi W, Zhi-qiang H, Jia-hong D (2015)
Sustained methylene blue staining to guide anatomic hepatectomy for hepatocellular carcinoma: Initial experience and technical details.
Surgery 158, 121-127 [PubMed:25791029]
[show Abstract]
Aoyama T, Fujikawa H, Cho H, Ogata T, Shirai J, Hayashi T, Rino Y, Masuda M, Oba MS, Morita S, Yoshikawa T (2015)
A methylene blue-assisted technique for harvesting lymph nodes after radical surgery for gastric cancer: a prospective, randomized, controlled study.
The American journal of surgical pathology 39, 266-273 [PubMed:25356528]
[show Abstract]
Zhang Z, Liao Y, Ai B, Liu C (2015)
Methylene blue staining: a new technique for identifying intersegmental planes in anatomic segmentectomy.
The Annals of thoracic surgery 99, 238-242 [PubMed:25440279]
[show Abstract]
Suwanarusk R, Russell B, Ong A, Sriprawat K, Chu CS, PyaePhyo A, Malleret B, Nosten F, Renia L (2015)
Methylene blue inhibits the asexual development of vivax malaria parasites from a region of increasing chloroquine resistance.
The Journal of antimicrobial chemotherapy 70, 124-129 [PubMed:25150147]
[show Abstract]
Yu JX, Li BH, Sun XM, Yuan J, Chi RA (2010)
Poly(amic acid)-modified biomass of baker's yeast for enhancement adsorption of methylene blue and basic magenta.
Applied biochemistry and biotechnology 160, 1394-1406 [PubMed:19277479]
[show Abstract]
Nakayama M, Nakamoto S, Iida C, Yoshimoto M (2009)
Removal of methylene blue from aqueous solution using a polarizable nanolayered manganese oxide film.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 25, 229-233 [PubMed:19212058]
[show Abstract]
Zolfaghari PS, Packer S, Singer M, Nair SP, Bennett J, Street C, Wilson M (2009)
In vivo killing of Staphylococcus aureus using a light-activated antimicrobial agent.
BMC microbiology 9, 27 [PubMed:19193212]
[show Abstract]
Bujdák J, Jureceková J, Bujdákova H, Lang K, Sersen F (2009)
Clay mineral particles as effficient carriers of methylene blue used for antimicrobial treatment.
Environmental science & technology 43, 6202-6207 [PubMed:19746714]
[show Abstract]
Rojas JC, Simola N, Kermath BA, Kane JR, Schallert T, Gonzalez-Lima F (2009)
Striatal neuroprotection with methylene blue.
Neuroscience 163, 877-889 [PubMed:19596056]
[show Abstract]
Shen JS, Yu T, Xie JW, Jiang YB (2009)
Photoluminescence of CdTe nanocrystals modulated by methylene blue and DNA. A label-free luminescent signaling nanohybrid platform.
Physical chemistry chemical physics : PCCP 11, 5062-5069 [PubMed:19562136]
[show Abstract]
Sobal G, Rodrigues M, Sinzinger H (2008)
Radioiodinated methylene blue--a promising agent for melanoma scintigraphy: labelling, stability and in vitro uptake by melanoma cells.
Anticancer research 28, 3691-3696 [PubMed:19189650]
[show Abstract]
Pavan FA, Mazzocato AC, Gushikem Y (2008)
Removal of methylene blue dye from aqueous solutions by adsorption using yellow passion fruit peel as adsorbent.
Bioresource technology 99, 3162-3165 [PubMed:17692516]
[show Abstract]
Lu Y, Jiao R, Chen X, Zhong J, Ji J, Shen P (2008)
Methylene blue-mediated photodynamic therapy induces mitochondria-dependent apoptosis in HeLa cell.
Journal of cellular biochemistry 105, 1451-1460 [PubMed:18980251]
[show Abstract]
Pavan FA, Lima EC, Dias SL, Mazzocato AC (2008)
Methylene blue biosorption from aqueous solutions by yellow passion fruit waste.
Journal of hazardous materials 150, 703-712 [PubMed:17597293]
[show Abstract]
Evora PR, Simon MR (2007)
Role of nitric oxide production in anaphylaxis and its relevance for the treatment of anaphylactic hypotension with methylene blue.
Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology 99, 306-313 [PubMed:17941276]
[show Abstract]
Ramsay RR, Dunford C, Gillman PK (2007)
Methylene blue and serotonin toxicity: inhibition of monoamine oxidase A (MAO A) confirms a theoretical prediction.
British journal of pharmacology 152, 946-951 [PubMed:17721552]
[show Abstract]
Yuan SH, Xiong Y, Wei M, Yan XJ, Zhang HZ, Zeng YX, Liang LZ (2007)
Sentinel lymph node detection using methylene blue in patients with early stage cervical cancer.
Gynecologic oncology 106, 147-152 [PubMed:17499345]
[show Abstract]
Garavito G, Bertani S, Rincon J, Maurel S, Monje MC, Landau I, Valentin A, Deharo E (2007)
Blood schizontocidal activity of methylene blue in combination with antimalarials against Plasmodium falciparum.
Parasite (Paris, France) 14, 135-140 [PubMed:17645185]
[show Abstract]
Heydrick SJ, Reed KL, Cohen PA, Aarons CB, Gower AC, Becker JM, Stucchi AF (2007)
Intraperitoneal administration of methylene blue attenuates oxidative stress, increases peritoneal fibrinolysis, and inhibits intraabdominal adhesion formation.
The Journal of surgical research 143, 311-319 [PubMed:17826794]
[show Abstract]
Tsuchiya T, Takeuchi T, Hayashida K, Shimizu H, Ando K, Harada E (2006)
Milk-derived lactoferrin may block tolerance to morphine analgesia.
Brain research 1068, 102-108 [PubMed:16380099]
[show Abstract]
Zhang X, Rojas JC, Gonzalez-Lima F (2006)
Methylene blue prevents neurodegeneration caused by rotenone in the retina.
Neurotoxicity research 9, 47-57 [PubMed:16464752]
[show Abstract]
Wang S, Boyjoo Y, Choueib A (2005)
A comparative study of dye removal using fly ash treated by different methods.
Chemosphere 60, 1401-1407 [PubMed:16054909]
[show Abstract]
Czímerová A, Jankovic L, Bujdák J (2004)
Effect of the exchangeable cations on the spectral properties of methylene blue in clay dispersions.
Journal of colloid and interface science 274, 126-132 [PubMed:15120287]
[show Abstract]
Clifton J, Leikin JB (2003)
Methylene blue.
American journal of therapeutics 10, 289-291 [PubMed:12845393]
[show Abstract]
Leyh RG, Kofidis T, Kofidis T, Strüber M, Fischer S, Knobloch K, Wachsmann B, Hagl C, Simon AR, Haverich A (2003)
Methylene blue: the drug of choice for catecholamine-refractory vasoplegia after cardiopulmonary bypass?
The Journal of thoracic and cardiovascular surgery 125, 1426-1431 [PubMed:12830064]
[show Abstract]
Martínez Portillo FJ, Fernández Arancibia MI, Bach S, Alken P, Jünemann KP (2002)
[Methylene blue: an effective therapeutic alternative for priapism induced by intracavernous injection of vasoactive agents].
Archivos espanoles de urologia 55, 303-308 [PubMed:12068762]
[show Abstract]
Evgenov OV, Sager G, Bjertnaes LJ (2001)
Methylene blue reduces lung fluid filtration during the early phase of endotoxemia in awake sheep.
Critical care medicine 29, 374-379 [PubMed:11246319]
[show Abstract]
Dutta K, Mukhopadhyay S, Bhattacharjee S, Chaudhuri B (2001)
Chemical oxidation of methylene blue using a Fenton-like reaction.
Journal of hazardous materials 84, 57-71 [PubMed:11376884]
[show Abstract]
Peer G, Itzhakov E, Wollman Y, Chernihovsky T, Grosskopf I, Segev D, Silverberg D, Blum M, Schwartz D, Iaina A (2001)
Methylene blue, a nitric oxide inhibitor, prevents haemodialysis hypotension.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 16, 1436-1441 [PubMed:11427637]
[show Abstract]
Segawa K, Minami K, Shiga Y, Shiraishi M, Sata T, Nakashima Y, Shigematsu A (2001)
Inhibitory effects of nicorandil on rat mesangial cell proliferation via the protein kinase G pathway.
Nephron 87, 263-268 [PubMed:11287762]
[show Abstract]
Cohen N, Robinson D, Ben-Ezzer J, Hemo Y, Hasharoni A, Wolmann Y, Otremski I, Nevo Z (2000)
Reduced NO accumulation in arthrotic cartilage by exposure to methylene blue.
Acta orthopaedica Scandinavica 71, 630-636 [PubMed:11145393]
[show Abstract]
BROOKS MM (1948)
Methylene blue, an antidote to altitude sickness.
The Journal of aviation medicine 19, 298 [PubMed:18873190]
Last Modified
24 November 2015