Methylene blue - wikipedia Methylene blue Not to be confused with methyl blue, new methylene blue, or methyl violet. Methylene blue Clinical data Trade names Urelene blue, Provayblue, Proveblue, other Synonyms CI 52015 AHFS / Drugs.com Monograph Pregnancy category AU : D US : X ( Contraindicated ) Routes of administration by mouth, IV ATC code none Legal status Legal status US : Medication Rx - only Identifiers IUPAC name 3, 7 - bis ( Dimethylamino ) - phenothiazin - 5 - ium chloride CAS Number 61 - 73 - 4 PubChem CID 6099 ChemSpider 5874 KEGG D10537 ChEBI CHEBI : 6872 ChEMBL CHEMBL405110 ECHA InfoCard 100.000. 469 Chemical and physical data Formula C H Cl N S Molar mass 319.85 g / mol 3D model ( JSmol ) Interactive image SMILES CN ( C ) c1ccc2c ( c1 ) sc - 3cc ( = ( N+ ) ( C ) C ) ccc3n2. ( Cl - ) 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 Key : CXKWCBBOMKCUKX - UHFFFAOYSA - M ( verify ) Methylene blue, also known as methylthioninium chloride, is a medication and dye. As a medication, it is mainly used to treat methemoglobinemia. 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 cyanide poisoning and urinary tract infections, but this use is no longer recommended. It is typically given by injection into a vein. Common side effects include headache, vomiting, confusion, shortness of breath, and high blood pressure. Other side effects include serotonin syndrome, red blood cell breakdown, and allergic reactions. Use often turns the urine, sweat, and stool blue to green in color. While use during pregnancy may harm the baby, not using in methemoglobinemia is likely more dangerous. Methylene blue is a thiazine dye. It works by converting the ferric iron in hemoglobin to ferrous iron. Methylene blue was first prepared in 1876 by Heinrich Caro. It is on the World Health Organization 's List of Essential Medicines, the most effective and safe medicines needed in a health system. In the United States, a 50 mg vial costs about 191.40 USD. In the United Kingdom, a 50 mg vial costs the NHS about £ 39.38. Contents 1 Medical uses 1.1 Methemoglobinemia 1.2 Combined with light 1.3 Urinary tract infection 1.4 Cyanide poisoning 1.5 Dye or stain 1.6 Placebo 1.7 Ifosfamide toxicity 1.8 Vasoplegic syndrome 2 Side effects 3 Chemistry 3.1 Preparation 3.2 Light absorption properties 4 Other uses 4.1 Redox indicator 4.2 Peroxide generator 4.3 Sulfide analysis 4.4 Water testing 4.5 Methylene blue value of fine aggregate 4.6 Biological staining 4.7 Aquaculture 5 History 6 Names 7 Research 7.1 Malaria 7.2 Alzheimer 's 7.3 Bipolar disorder 7.4 Viruses 8 See also 9 References 10 External links Medical uses Methemoglobinemia Methylene blue is employed as a medication for the treatment of methemoglobinemia. This can arise from ingestion of certain pharmaceuticals, toxins, or broad beans. Normally, through the NADH or NADPH dependent methemoglobin reductase enzymes, methemoglobin is reduced back to hemoglobin. When large amounts of methemoglobin occur secondary to toxins, methemoglobin reductases are overwhelmed. Methylene blue, when injected intravenously as an antidote, is itself first reduced to leucomethylene blue, which then reduces the heme group from methemoglobin to hemoglobin. Methylene blue can reduce the half life of methemoglobin from hours to minutes. At high doses, however, methylene blue actually induces methemoglobinemia, reversing this pathway. Combined with light Methylene blue combined with light has been used to treat resistant plaque psoriasis. Urinary tract Infection Methylene blue is a component of a frequently prescribed urinary analgesic / anti-infective / anti-spasmodic known as `` Prosed DS '', a combination of drugs which also contains phenyl salicylate, benzoic acid, hyoscyamine sulfate, and methenamine ( aka hexamethylenetetramine and not to be confused with ' methanamine ' ). Cyanide poisoning Since its reduction potential is similar to that of oxygen and can be reduced by components of the electron transport chain, large doses of methylene blue are sometimes used as an antidote to potassium cyanide poisoning, a method first successfully tested in 1933 by Dr. Matilda Moldenhauer Brooks in San Francisco, although first demonstrated by Bo Sahlin of Lund University, in 1926. Dye or stain Human cheek cells stained with methylene blue Methylene blue is used in endoscopic polypectomy as an adjunct to saline or epinephrine, and is used for injection into the submucosa around the polyp to be removed. This allows the submucosal tissue plane to be identified after the polyp is removed, which is useful in determining if more tissue needs to be removed, or if there has been a high risk for perforation. Methylene blue is also used as a dye in chromoendoscopy, and is sprayed onto the mucosa of the gastrointestinal tract in order to identify dysplasia, or pre-cancerous lesions. Intravenously injected methylene blue is readily released into the urine and thus can be used to test the urinary tract for leaks or fistulas. In surgeries such as sentinel lymph node dissections, methylene blue can be used to visually trace the lymphatic drainage of tested tissues. Similarly, methylene blue is added to bone cement in orthopedic operations to provide easy discrimination between native bone and cement. Additionally, methylene blue accelerates the hardening of bone cement, increasing the speed at which bone cement can be effectively applied. Methylene blue is used as an aid to visualisation / orientation in a number of medical devices, including a Surgical sealant film, TissuePatch. When methylene blue is `` polychromed '' ( oxidized in solution or `` ripened '' by fungal metabolism, as originally noted in the thesis of Dr. D.L. Romanowsky in the 1890s ), it gets serially demethylated and forms all the tri -, di -, mono - and non-methyl intermediates, which are Azure B, Azure A, Azure C, and thionine, respectively. This is the basis of the basophilic part of the spectrum of Romanowski - Giemsa effect. If only synthetic Azure B and Eosin Y is used, it may serve as a standardized Giemsa stain ; but, without methylene blue, the normal neutrophilic granules tend to overstain and look like toxic granules. On the other hand, if methylene blue is used it might help to give the normal look of neutrophil granules and may also enhance the staining of nucleoli and polychromatophilic RBCs ( reticulocytes ). A traditional application of methylene blue is the intravital or supravital staining of nerve fibers, an effect first described by Paul Ehrlich in 1887. A dilute solution of the dye is either injected into tissue or applied to small freshly removed pieces. The selective blue coloration develops with exposure to air ( oxygen ) and can be fixed by immersion of the stained specimen in an aqueous solution of ammonium molybdate. Vital methylene blue was formerly much used for examining the innervation of muscle, skin and internal organs. The mechanism of selective dye uptake is incompletely understood ; vital staining of nerve fibers in skin is prevented by ouabain, a drug that inhibits the Na / K - ATPase of cell membranes. Placebo Methylene blue has been used as a placebo ; physicians would tell their patients to expect their urine to change color and view this as a sign that their condition had improved. This same side effect makes methylene blue difficult to test in traditional placebo - controlled clinical studies. Ifosfamide toxicity Another use of methylene blue is to treat ifosfamide neurotoxicity. Methylene blue was first reported for treatment and prophylaxis of ifosfamide neuropsychiatric toxicity in 1994. A toxic metabolite of ifosfamide, chloroacetaldehyde ( CAA ), disrupts the mitochondrial respiratory chain, leading to an accumulation of nicotinamide adenine dinucleotide hydrogen ( NADH ). Methylene blue acts as an alternative electron acceptor, and reverses the NADH inhibition of hepatic gluconeogenesis while also inhibiting the transformation of chloroethylamine into chloroacetaldehyde, and inhibits multiple amine oxidase activities, preventing the formation of CAA. The dosing of methylene blue for treatment of ifosfamide neurotoxicity varies, depending upon its use simultaneously as an adjuvant in ifosfamide infusion, versus its use to reverse psychiatric symptoms that manifest after completion of an ifosfamide infusion. Reports suggest that methylene blue up to six doses a day have resulted in improvement of symptoms within 10 minutes to several days. Alternatively, it has been suggested that intravenous methylene blue every six hours for prophylaxis during ifosfamide treatment in patients with history of ifosfamide neuropsychiatric toxicity. Prophylactic administration of methylene blue the day before initiation of ifosfamide, and three times daily during ifosfamide chemotherapy has been recommended to lower the occurrence of ifosfamide neurotoxicity. Vasoplegic syndrome Some literature has reported the use of methylene blue as an adjunct in the management of people experiencing vasoplegic syndrome after cardiac surgery. Side effects Cardiovascular Central Nervous System Dermatologic Gastrointestinal Genito - urinary Hematologic Hypertension Precordial pain Dizziness Mental confusion Headache Fever Staining of skin Injection site necrosis ( SC ) Fecal discoloration Nausea Vomiting Abdominal pain Discoloration of urine ( doses over 80 μg ) Bladder irritation Anemia Methylene blue is a monoamine oxidase inhibitor ( MAOI ), and if infused intravenously at doses exceeding 5 mg / kg, may precipitate serious serotonin toxicity, serotonin syndrome, if combined with any selective serotonin reuptake inhibitors ( SSRIs ) or other serotonin reuptake inhibitor ( e.g., duloxetine, sibutramine, venlafaxine, clomipramine, imipramine ). It causes hemolytic anemia in carriers of the G6PD ( favism ) enzymatic deficiency. Chemistry Methylene blue is a formal derivative of phenothiazine. It is a dark green powder that yields a blue solution in water. The hydrated form has 3 molecules of water per unit of methylene blue. Methylene blue has a pH of 3 in water ( 10g / l ) at 25 ° C ( 77 ° F ). Preparation This compound is prepared by oxidation of dimethyl - 4 - phenylenediamine in the presence of sodium thiosulfate. Light absorption properties Absorption spectrum of methylene blue, in terms of the molar extinction coefficient ( base 10 logarithm ). In this dataset a peak absorbance of 1.7 ( i.e. 98 % of transmitted light absorbed ) was observed with 665 nm light passing through 1 cm of 10 micromolar methylene blue solution. The maximum absorption of light is near 670 nm. The specifics of absorption depend on a number of factors, including protonation, adsorption to other materials, and metachromasy - the formation of dimers and higher - order aggregates depending on concentration and other interactions : Species Absorption peak Extinction coefficient ( dm / mole cm ) MB ( solution ) 664 95000 MBH ( solution ) 741 76000 ( MB ) ( solution ) 605 132000 ( MB ) ( solution ) 580 110000 MB ( adsorbed on clay ) 673 116000 MBH ( adsorbed on clay ) 763 86000 ( MB ) ( adsorbed on clay ) 596 80000 ( MB ) ( adsorbed on clay ) 570 114000 Other uses A volumetric flask of a methylene blue solution Redox indicator Methylene blue is widely used as a redox indicator in analytical chemistry. Solutions of this substance are blue when in an oxidizing environment, but will turn colorless if exposed to a reducing agent. The redox properties can be seen in a classical demonstration of chemical kinetics in general chemistry, the `` blue bottle '' experiment. Typically, a solution is made of glucose ( dextrose ), methylene blue, and sodium hydroxide. Upon shaking the bottle, oxygen oxidizes methylene blue, and the solution turns blue. The dextrose will gradually reduce the methylene blue to its colorless, reduced form. Hence, when the dissolved dextrose is entirely consumed, the solution will turn blue again. The redox midpoint potential E ' is + 0.011 mV. Peroxide generator Methylene blue is also a photosensitizer used to create singlet oxygen when exposed to both oxygen and light. It is used in this regard to make organic peroxides by a Diels - Alder reaction which is spin forbidden with normal atmospheric triplet oxygen. Sulfide analysis The formation of methylene blue after the reaction of hydrogen sulfide with dimethyl - p - phenylenediamine and iron ( III ) at pH 0.4 -- 0.7 is used to determine by photometric measurements sulfide concentration in the range 0.020 to 1.50 mg / L ( 20 ppb to 1.5 ppm ). The test is very sensitive and the blue coloration developing upon contact of the reagents with dissolved H S is stable for 60 min. Ready - to - use kits such as the Spectroquant sulfide test facilitate routine analyses. The methylene blue sulfide test is a convenient method often used in soil microbiology to quickly detect in water the metabolic activity of sulfate reducing bacteria ( SRB ). It should be observed that in this test, methylene blue is a product of reaction and not a reagent. The addition of a strong reducing agent, such as ascorbic acid, to a sulfide - containing solution is sometimes used to prevent sulfide oxidation from atmospheric oxygen. Although it is certainly a sound precaution for the determination of sulfide with an ion selective electrode, it might however hamper the development of the blue color if the freshly formed methylene blue is also reduced, as described here above in the paragraph on redox indicator. Water testing Further information : MBAS assay A color reaction in an acidified, aqueous methylene blue solution containing chloroform can detect anionic surfactants in a water sample. Such a test is known as an MBAS assay ( methylene blue active substances assay ). The MBAS assay can not distinguish between specific surfactants, however. Some examples of anionic surfactants are carboxylates, phosphates, sulfates, and sulfonates. Methylene blue value of fine aggregate Methylene blue value reflects the amount of clay minerals in aggregate samples. Methylene blue solution is successively added to fine aggregate which is being agitating in water. The presence of free dye solution can be checked with stain test on a filter paper. Biological staining In biology methylene blue is used as a dye for a number of different staining procedures, such as Wright 's stain and Jenner 's stain. Since it is a temporary staining technique, methylene blue can also be used to examine RNA or DNA under the microscope or in a gel : as an example, a solution of methylene blue can be used to stain RNA on hybridization membranes in northern blotting to verify the amount of nucleic acid present. While methylene blue is not as sensitive as ethidium bromide, it is less toxic and it does not intercalate in nucleic acid chains, thus avoiding interference with nucleic acid retention on hybridization membranes or with the hybridization process itself. It can also be used as an indicator to determine whether eukaryotic cells such as yeast are alive or dead. The methylene blue is reduced in viable cells, leaving them unstained. However dead cells are unable to reduce the oxidized methylene blue and the cells are stained blue. Methylene blue can interfere with the respiration of the yeast as it picks up hydrogen ions made during the process. Aquaculture Methylene blue is used in aquaculture and by tropical fish hobbyists as a treatment for fungal infections. It can also be effective in treating fish infected with ich although a combination of malachite green and formaldehyde is far more effective against the parasitic protozoa Ichthyophthirius multifiliis. It is usually used to protect newly laid fish eggs from being infected by fungus or bacteria. This is useful when the hobbyist wants to artificially hatch the fish eggs. Methylene Blue is also very effective when used as part of a `` medicated fish bath '' for treatment of ammonia, nitrite, and cyanide poisoning as well as for topical and internal treatment of injured or sick fish as a `` first response ''. History Methylene blue has been described as `` the first fully synthetic drug used in medicine. '' Methylene blue was first prepared in 1876 by German chemist Heinrich Caro. Its use in the treatment of malaria was pioneered by Paul Guttmann and Paul Ehrlich in 1891. During this period before the first World War, researchers like Ehrlich believed that drugs and dyes worked in the same way, by preferentially staining pathogens and possibly harming them. Methylene blue continued to be used in the second World War, where it was not well liked by soldiers, who observed, `` Even at the loo, we see, we pee, navy blue. '' Antimalarial use of the drug has recently been revived. It was discovered to be an antidote to carbon monoxide poisoning and cyanide poisoning in 1933 by Matilda Brooks. The blue urine was used to monitor psychiatric patients ' compliance with medication regimes. This led to interest - from the 1890s to the present day - in the drug 's antidepressant and other psychotropic effects. It became the lead compound in research leading to the discovery of chlorpromazine. Names The International Nonproprietary Name ( INN ) of methylene blue is methylthioninium chloride. Research Malaria Methylene blue was identified by Paul Ehrlich about 1891 as a possible treatment for malaria. It disappeared as an anti-malarial during the Pacific War in the tropics, since American and Allied soldiers disliked its two prominent, but reversible side effects : turning the urine blue or green, and the sclera ( the whites of the eyes ) blue. Interest in its use as an anti-malarial has recently been revived, especially due to its low price. Several clinical trials are in progress, trying to find a suitable drug combination. According to studies on children in Africa, it appears to have efficacy against malaria, but the attempts to combine methylene blue with chloroquine were disappointing. Alzheimer 's A Phase 3 clinical trial of LMTM ( TauRx0237 or LMT - X ), a derivative of methylene blue, failed to show any benefit against cognitive or functional decline in people with mild to moderate Alzheimer 's disease. Disease progression for both the drug and the placebo were practically identical. Bipolar disorder Methylene blue has been studied as an adjunctive medication in the treatment of bipolar disorder. Viruses It has been studied in AIDS - related Kaposi 's sarcoma, West Nile virus, and to inactivate staphylococcus aureus, and HIV - 1. Phenothiazine dyes and light have been known to have virucidal properties for over 70 years. See also New methylene blue Phenothiazine structure Rember, investigational drug for Alzheimer 's disease containing methylene blue Romanowsky stain Methyl violet Gentian violet Fluorescein Prussian blue Egyptian Blue Methyl blue Han Purple Potassium ferrocyanide Potassium ferricyanide References ^ Jump up to : `` Methylene Blue ''. The American Society of Health - System Pharmacists. Archived from the original on 10 May 2017. Retrieved 8 January 2017. Jump up ^ Hamilton, Richart ( 2015 ). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab - Coat Edition. 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External links NIH - Methylene blue test Methylene blue at stainsfile Antidotes ( V03AB ) Nervous system Nerve agent / Organophosphate poisoning Atropine Biperiden Diazepam Oximes Obidoxime Pralidoxime see also : Cholinesterase Barbiturate overdose Bemegride Ethamivan Benzodiazepine overdose Cyprodenate Flumazenil GHB overdose Physostigmine SCH - 50911 Opioid overdose Diprenorphine Doxapram Nalmefene Nalorphine Naloxone Naltrexone Reversal of neuromuscular blockade Sugammadex Circulatory system Beta blocker Glucagon Digoxin toxicity Digoxin Immune Fab Heparin Protamine Other Arsenic poisoning Dimercaprol Succimer Cyanide poisoning 4 - Dimethylaminophenol Hydroxocobalamin nitrite Amyl nitrite Sodium nitrite Sodium thiosulfate Hydrofluoric acid Calcium gluconate Methanol / Ethylene glycol poisoning Primary alcohols : Ethanol Fomepizole Paracetamol toxicity ( Acetaminophen ) Acetylcysteine Glutathione Methionine Toxic metals ( cadmium lead mercury thallium ) Dimercaprol Edetates Prussian blue Other iodine - 131 Potassium iodide Methylthioninium chloride oxidizing agent Potassium permanganate Prednisolone / promethazine Emetic Copper sulfate Ipecacuanha Syrup of ipecac WHO - EM Withdrawn from market Clinical trials : Phase III Never to phase III Microbial and histological stains Iron / hemosiderin Prussian blue Lipids Sudan stain Sudan II Sudan III Sudan IV Oil Red O Sudan Black B Carbohydrates Periodic acid -- Schiff stain Amyloid Congo red Bacteria Gram stain Methyl violet / Gentian violet Safranin Ziehl -- Neelsen stain / acid - fast Carbol fuchsin / Fuchsine Methylene blue Auramine - rhodamine stain Auramine O Rhodamine B Connective tissue trichrome stain : Masson 's trichrome stain / Lillie 's trichrome Light Green SF yellowish Biebrich scarlet Phosphomolybdic acid Fast Green FCF Van Gieson 's stain Other H&E stain Haematoxylin Eosin Y Silver stain Grocott 's methenamine silver stain Warthin -- Starry stain Methyl blue Wright 's stain Giemsa stain Gömöri trichrome stain Neutral red Janus Green B Alcian blue stain Movat 's stain Jaswant Singh -- Bhattacharji ( JSB ) stain Tissue stainability Acidophilic Basophilic Chromophobic Glutamate receptor modulators Ionotropic glutamate receptor modulators AMPAR Agonists : Main site agonists : 5 - Fluorowillardiine Acromelic acid ( acromelate ) AMPA BOAA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine ; Positive allosteric modulators : Aniracetam Cyclothiazide CX - 516 CX - 546 CX - 614 Farampator ( CX - 691, ORG - 24448 ) CX - 717 CX - 1739 CX - 1942 Diazoxide Hydrochlorothiazide ( HCTZ ) IDRA - 21 LY - 392098 LY - 395153 LY - 404187 LY - 451646 LY - 503430 Mibampator ( LY - 451395 ) Nooglutyl ORG - 26576 Oxiracetam PEPA PF - 04958242 Piracetam Pramiracetam S - 18986 Tulrampator ( S - 47445, CX - 1632 ) Antagonists : ACEA - 1011 ATPO Becampanel Caroverine CNQX Dasolampanel DNQX Fanapanel ( MPQX ) GAMS Kaitocephalin Kynurenic acid Kynurenine Licostinel ( ACEA - 1021 ) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel ; Negative allosteric modulators : Barbiturates ( e.g., pentobarbital, sodium thiopental ) Cyclopropane Enflurane Ethanol ( alcohol ) Evans blue GYKI - 52466 GYKI - 53655 Halothane Irampanel Isoflurane Perampanel Pregnenolone sulfate Sevoflurane Talampanel ; Unknown / unsorted antagonists : Minocycline KAR Agonists : Main site agonists : 5 - Bromowillardiine 5 - Iodowillardiine Acromelic acid ( acromelate ) AMPA ATPA Domoic acid Glutamate Ibotenic acid Kainic acid LY - 339434 Proline Quisqualic acid SYM - 2081 ; Positive allosteric modulators : Cyclothiazide Diazoxide Enflurane Halothane Isoflurane Antagonists : ACEA - 1011 CNQX Dasolampanel DNQX GAMS Kaitocephalin Kynurenic acid Licostinel ( ACEA - 1021 ) LY - 382884 NBQX NS102 Selurampanel Tezampanel Theanine Topiramate UBP - 302 ; Negative allosteric modulators : Barbiturates ( e.g., pentobarbital, sodium thiopental ) Enflurane Ethanol ( alcohol ) Evans blue NS - 3763 Pregnenolone sulfate NMDAR Agonists : Main site agonists : AMAA Aspartate Glutamate Homocysteic acid ( L - HCA ) Homoquinolinic acid Ibotenic acid NMDA Proline Quinolinic acid Tetrazolylglycine Theanine ; Glycine site agonists : β - Fluoro - D - alanine ACBD ACC ( ACPC ) ACPD AK - 51 Apimostinel ( NRX - 1074 ) B6B21 CCG D - Alanine D - Cycloserine D - Serine DHPG Dimethylglycine Glycine HA - 966 L - 687414 L - Alanine L - Serine Milacemide Neboglamine ( nebostinel ) Rapastinel ( GLYX - 13 ) Sarcosine ; Polyamine site agonists : Neomycin Spermidine Spermine ; Other positive allosteric modulators : 24S - Hydroxycholesterol DHEA ( prasterone ) DHEA sulfate ( prasterone sulfate ) Epipregnanolone sulfate Pregnenolone sulfate SAGE - 201 SAGE - 301 SAGE - 718 Antagonists : Competitive antagonists : AP5 ( APV ) AP7 CGP - 37849 CGP - 39551 CGP - 39653 CGP - 40116 CGS - 19755 CPP Kaitocephalin LY - 233053 LY - 235959 LY - 274614 MDL - 100453 Midafotel ( d - CPPene ) NPC - 12626 NPC - 17742 PBPD PEAQX Perzinfotel PPDA SDZ - 220581 Selfotel ; Glycine site antagonists : 4 - Cl - KYN ( AV - 101 ) 5, 7 - DCKA 7 - CKA ACC ACEA - 1011 ACEA - 1328 Apimostinel ( NRX - 1074 ) AV - 101 Carisoprodol CGP - 39653 CNQX D - Cycloserine DNQX Felbamate Gavestinel GV - 196771 Harkoseride Kynurenic acid Kynurenine L - 689560 L - 701324 Licostinel ( ACEA - 1021 ) LU - 73068 MDL - 105519 Meprobamate MRZ 2 / 576 PNQX Rapastinel ( GLYX - 13 ) ZD - 9379 ; Polyamine site antagonists : Arcaine Co 101676 Diaminopropane Diethylenetriamine Huperzine A Putrescine ; Uncompetitive pore blockers ( mostly dizocilpine site ) : 2 - MDP 3 - HO - PCP 3 - MeO - PCE 3 - MeO - PCMo 3 - MeO - PCP 4 - MeO - PCP 8A - PDHQ 18 - MC α - Endopsychosin Alaproclate Alazocine ( SKF - 10047 ) Amantadine Aptiganel Argiotoxin - 636 Arketamine ARL - 12495 ARL - 15896 - AR ARL - 16247 Budipine Coronaridine Delucemine ( NPS - 1506 ) Dexoxadrol Dextrallorphan Dextromethadone Dextromethorphan Dextrorphan Dieticyclidine Diphenidine Dizocilpine Ephenidine Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan Levomilnacipran Levorphanol Loperamide Memantine Methadone Methorphan Methoxetamine Methoxphenidine Milnacipran Morphanol NEFA Neramexane Nitromemantine Noribogaine Norketamine Orphenadrine PCPr PD - 137889 Pethidine ( meperidine ) Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Rimantadine Rolicyclidine Sabeluzole Tabernanthine Tenocyclidine Tiletamine Tramadol ; Ifenprodil ( NR2B ) site antagonists : Besonprodil Buphenine ( nylidrin ) CO-101244 ( PD - 174494 ) Eliprodil Haloperidol Isoxsuprine Radiprodil ( RGH - 896 ) Rislenemdaz ( CERC - 301, MK - 0657 ) Ro 8 - 4304 Ro 25 - 6981 Safaprodil Traxoprodil ( CP - 101606 ) ; NR2A - selective antagonists : MPX - 004 MPX - 007 TCN - 201 TCN - 213 ; Cations : Hydrogen Magnesium Zinc ; Alcohols / volatile anesthetics / related : Benzene Butane Chloroform Cyclopropane Desflurane Diethyl ether Enflurane Ethanol ( alcohol ) Halothane Hexanol Isoflurane Methoxyflurane Nitrous oxide Octanol Sevoflurane Toluene Trichloroethane Trichloroethanol Trichloroethylene Urethane Xenon Xylene ; Unknown / unsorted antagonists : ARR - 15896 Bumetanide Caroverine Conantokin D - αAA Dexanabinol Flufenamic acid Flupirtine FPL - 12495 FR - 115427 Furosemide Hodgkinsine Ipenoxazone ( MLV - 6976 ) MDL - 27266 Metaphit Minocycline MPEP Niflumic acid Pentamidine Pentamidine isethionate Piretanide Psychotridine Transcrocetin ( saffron ) See also : Receptor / signaling modulators Metabotropic glutamate receptor modulators Glutamate metabolism / transport modulators Metabotropic glutamate receptor modulators Group I mGluR Agonists : ACPD DHPG Glutamate Ibotenic acid Quisqualic acid Ro01 - 6128 Ro67 - 4853 Ro67 - 7476 VU - 71 Theanine Antagonists : BAY 36 - 7620 CPCCOEt Cyclothiazide LY - 367,385 LY - 456,236 MCPG NPS - 2390 mGluR Agonists : ACPD ADX - 47273 CDPPB CHPG DFB DHPG Glutamate Ibotenic acid Quisqualic acid VU - 1545 Antagonists : CTEP DMeOB LY - 344,545 Mavoglurant MCPG NPS - 2390 Remeglurant SIB - 1757 SIB - 1893 ; Negative allosteric modulators : Basimglurant Dipraglurant Fenobam GRN - 529 MPEP MTEP Raseglurant Group II mGluR Agonists : BINA CBiPES DCG - IV Eglumegad Glutamate Ibotenic acid LY - 379,268 LY - 404,039 ( pomaglumetad ) LY - 487,379 LY - 566,332 MGS - 0028 Pomaglumetad methionil ( LY - 2140023 ) Talaglumetad ; Positive allosteric modulators : JNJ - 40411813 ( ADX - 71149 ) Antagonists : APICA CECXG EGLU HYDIA LY - 307,452 LY - 341,495 MCPG MGS - 0039 PCCG - 4 ; Negative allosteric modulators : Decoglurant RO4491533 mGluR Agonists : CBiPES DCG - IV Eglumegad Glutamate Ibotenic acid LY - 379,268 LY - 404,039 ( pomaglumetad ) LY - 487,379 MGS - 0028 Pomaglumetad methionil ( LY - 2140023 ) Talaglumetad Antagonists : APICA CECXG EGLU HYDIA LY - 307,452 LY - 341,495 MCPG MGS - 0039 ; Negative allosteric modulators : Decoglurant RO4491533 Group III mGluR Agonists : Glutamate L - AP4 PHCCC VU - 001,171 VU - 0155, 041 ; Positive allosteric modulators : Foliglurax MPEP Antagonists : CPPG MAP4 MPPG MSOP MTPG UBP - 1112 mGluR Agonists : Glutamate L - AP4 Antagonists : CPPG MAP4 MPPG MSOP MTPG UBP - 1112 mGluR Agonists : AMN082 Glutamate L - AP4 Antagonists : CPPG MAP4 MMPIP MPPG MSOP MTPG UBP - 1112 mGluR Agonists : DCPG Glutamate L - AP4 Antagonists : CPPG MAP4 MPPG MSOP MTPG UBP - 1112 See also : Receptor / signaling modulators Ionotropic glutamate receptor modulators Glutamate metabolism / transport modulators Monoamine metabolism modulators Non-specific AAAD Substrates → Products : L - DOPA ( levodopa ) → Dopamine 5 - HTP → Serotonin L - Histidine → Histamine Phenylalanine → Phenethylamine L - Tyrosine → Tyramine Tryptophan → Tryptamine Inhibitors : Benserazide Carbidopa DFMD Genistein Methyldopa MAO Substrates → Products ( with ALDH / ALR ) : Epinephrine ( adrenaline ) → DHMA Metanephrine → MHPG / VMA Norepinephrine ( noradrenaline ) → DHMA Normetanephrine → MHPG / VMA Dopamine → DOPAC 3 - Methoxytyramine → HVA Serotonin → 5 - HIAA Inhibitors : Non-selective : Benmoxin Caroxazone Echinopsidine Furazolidone Guineesine Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine Inhibitors : MAO - A-selective : Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 ( Tyrima ) Eprobemide Esuprone Harmala alkaloids ( e.g., harmine, harmaline, harman, norharman, tetrahydroharmine ) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone Inhibitors : MAO - B selective : Adarigiline Almoxatone D - Deprenyl Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline Rasagiline Safinamide Selegiline ( L - Deprenyl ) Sembragiline Phenethylamines ( dopamine, epinephrine, norepinephrine ) PAH Substrates → Products : Phenylalanine → Tyrosine Inhibitors : 3, 4 - Dihydroxystyrene TH Substrates → Products : Tyrosine → L - DOPA ( levodopa ) Inhibitors : 2 - Hydroxyestradiol 2 - Hydroxyestrone 3 - Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone DBH Substrates → Products : Dopamine → Norepinephrine ( Noradrenaline ) Inhibitors : Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone PNMT Substrates → Products : Norepinephrine ( noradrenaline ) → Epinephrine ( adrenaline ) Inhibitors : CGS - 19281A SKF - 64139 SKF - 7698 COMT Substrates → Products : Dopamine → 3 - Methoxytyramine DOPAC → Homovanillic acid Norepinephrine → Normetanephrine Epinephrine → Metanephrine DOPEG → MOPEG DOMA → VMA 2 - Hydroxyestradiol → 2 - Methoxyestradiol 2 - Hydroxyestrone → 2 - Methoxyestrone 4 - Hydroxyestradiol → 4 - Methoxyestradiol 4 - Hydroxyestrone → 4 - Methoxyestrone Inhibitors : 2 - Hydroxyestradiol 2 - Hydroxyestrone Entacapone Nitecapone Opicapone Tolcapone Tryptamines ( serotonin, melatonin ) TPH Substrates → Products : Tryptophan → 5 - HTP Inhibitors : AGN - 2979 Fenclonine ( PCPA ) Telotristat ethyl AANAT Substrates → Products : Serotonin → N - Acetylserotonin ASMT Substrates → Products : N - Acetylserotonin → Melatonin Histamine HDC Substrates → Products : L - Histidine → Histamine Inhibitors : Catechin Meciadanol Naringenin Tritoqualine HNMT Substrates → Products : Histamine → N - Methylhistamine Inhibitors : Amodiaquine Diphenhydramine Harmaline Metoprine Quinacrine SKF - 91,488 Tacrine DAO Substrates → Products : Histamine → Imidazole acetic acid Inhibitors : Pimagedine ( aminoguanidine ) See also : Receptor / signaling modulators Adrenergics Dopaminergics Melatonergics Serotonergics Monoamine reuptake inhibitors Monoamine releasing agents Monoamine neurotoxins Tricyclics Classes Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene Antidepressants ( TCAs and TeCAs ) 7 - OH - Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Azipramine Batelapine Butriptyline Cianopramine Ciclazindol Ciclopramine Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine ( balipramine ) Desipramine ( desmethylimipramine ) Desmethylclomipramine Desmethyltrimipramine Dibenzepin Dimetacrine Dosulepin ( dothiepin ) Doxepin Enprazepine Esmirtazapine Fantridone Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mianserin Mirtazapine Monometacrine Naranol Nitroxazepine Norbutriptyline Nordoxepin Northiaden ( nordosulepin ) Nortriptyline ( noramitriptyline ) Noxiptiline Octriptyline Opipramol Oxaprotiline Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Setiptiline ( teciptiline ) Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine Antihistamines Azatadine Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Phenindamine Pimethixene Promethazine Propiomazine Rupatadine Thiazinamium Antipsychotics Acetophenazine Alimemazine Amoxapine Asenapine Butaclamol Butaperazine Carfenazine ( carphenazine ) Carpipramine Chlorpromazine Chlorprothixene Ciclindole Citatepine Clocapramine Clomacran Clorotepine Clotiapine Clozapine Cyanothepin Doclothepin Docloxythepin Erizepine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Isofloxythepin Levomepromazine / Methotrimeprazine Loxapine Lurasidone Maroxepin Meperathiepin Mesoridazine Metiapine Metitepine Metoxepin Mosapramine Naranol Octomethothepin Olanzapine Oxyclothepin Oxyprothepin Pentiapine Peradithiepin Perathiepin Perazine Perphenazine Periciazine Pinoxepin Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Savoxepin / Cipazoxapine Sulforidazine Tenilapine Thiethylperazine Thiopropazate Thioridazine Thiothixene Tilozepine Traboxopine Trifluoperazine Triflupromazine Trifluthepin Zotepine Zuclopenthixol Anticonvulsants Carbamazepine Dizocilpine Eslicarbazepine Eslicarbazepine acetate Etazepine Licarbazepine Oxcarbazepine Oxitriptyline Rispenzepine Others Adosopine Aminopromazine Atiprosin Beloxepin Benzoctamine Carvedilol Cidoxepin Cyclobenzaprine Damotepine Darenzepine Elanzepine Fluradoline Methylene blue Monatepil Nuvenzepine Oxetorone Perlapine P7C3 Pinadoline Pirenzepine Pirolate Pitrazepin Pizotifen Profenamine Serazapine Siltenzepine Telenzepine Tipindole Tropatepine Zolenzepine Pharmacy and pharmacology portal Medicine portal Retrieved from `` https://en.wikipedia.org/w/index.php?title=Methylene_blue&oldid=831573390 '' Categories : Drugs not assigned an ATC code Antidotes Histology Redox indicators Thiazine dyes Vital stains World Health Organization essential medicines Monoamine oxidase inhibitors Phenothiazines Chlorides Hidden categories : Webarchive template wayback links CS1 French - language sources ( fr ) Template : drugs.com link with non-standard subpage Drugs with non-standard legal status ECHA InfoCard ID from Wikidata Chemical pages without DrugBank identifier Articles without UNII source Pages using div col without cols and colwidth parameters RTT Talk Contents About Wikipedia تۆرکجه Català Čeština Dansk Deutsch Español Esperanto فارسی Français 한국어 Հայերեն Bahasa Indonesia Íslenska Italiano Nederlands 日本 語 ଓଡ଼ିଆ Polski Português Русский Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska Українська Tiếng Việt 中文 19 more Edit links This page was last edited on 21 March 2018, at 07 : 43. 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Question: what color is methylene blue in the reduced state
Answer: colorless