Methylene blue
IUPAC name	3,7-bis(Dimethylamino)- phenazathionium chloride Tetramethylthionine chloride
Identifiers
CAS number	61-73-4
SMILES	CN(C)c3ccc2nc1ccc(N(C) C)cc1[s+]c2c3.[Cl-]
Properties
Molecular formula	C16H18N3ClS
Molar mass	319.85 g/mol
Melting point	100-110 °C (with decomposion) Image File history File links Methylene_blue. ... Image File history File links Size of this preview: 800 × 428 pixel Image in higher resolution (1100 × 589 pixel, file size: 148 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Methylene blue ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	Decomposes Italic text This article is about the boiling point of liquids. ...
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Methylene blue is a heterocyclic aromatic chemical compound with molecular formula: C₁₆H₁₈ClN₃S. It has many uses in a range of different fields, such as biology or chemistry. At room temperature it appears as a solid, odorless, dark green powder, that yields a blue solution when dissolved in water. Methylene blue should not be confused with methyl blue, another histology stain, new methylene blue, nor with the methyl violets often used as pH indicators. The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... Heterocyclic compounds are substances which contain a ring structure as found in benzene and the aromatic compounds, or aromatic hydrocarbons, but in which other atoms than carbon, such as sulfur, oxygen or nitrogen are found as part of the ring. ... Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. ... Look up chemical compound in Wiktionary, the free dictionary. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... This article is about the chemical element. ... For the song by Girls Aloud see Biology (song) Biology studies the variety of life (clockwise from top-left) E. coli, tree fern, gazelle, Goliath beetle Biology (from Greek: βίος, bio, life; and λόγος, logos, speech lit. ... For other uses, see Chemistry (disambiguation). ... H2O and HOH redirect here. ... Structural formula of methyl blue Methyl blue, also known as Cotton blue, Helvetia blue, or Acid blue 93, is a chemical compound used as a stain in histology. ... A thin section of lung tissue stained with hematoxylin and eosin. ... New methylene blue (also NMB) is an organic staining agent used in diagnostic cytology and histopathology. ... Structure of Methyl Violet 2B Methyl violet is the name given to a group of similar chemicals used as pH indicators and dyes. ... Acids and bases: Acid-base extraction Acid-base reaction Acid dissociation constant Acidity function Buffer solutions pH Proton affinity Self-ionization of water Acids: Lewis acids Mineral acids Organic acids Strong acids Superacids Weak acids Bases: Lewis bases Organic bases Strong bases Superbases Non-nucleophilic bases Weak bases edit A...

Uses

Chemistry

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 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 oxygen is entirely consumed, the solution will turn colorless. Methylene blue is also used to make the reaction between Fehling's solution and reducing sugars more visible. A redox indicator (also called an oxidation-reduction indicator or a potentiometric indicator) is an indicator that undergoes a definite colour change at a specific oxidation potential. ... This article does not cite any references or sources. ... In physical chemistry, chemical kinetics or reaction kinetics is the study of reaction rates in a chemical reaction. ... A space-filling model of glucose Glucose, a simple monosaccharide sugar, is one of the most important carbohydrates and is used as a source of energy in animals and plants. ... Flash point Non-flammable. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... Fehlings solution is a solution used to deferentiate between aldehyde or ketone functional groups. ...

Biology

In biology methylene blue is used as a dye for a number of different staining procedures, such as Gram's stain, 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. Look up dye in Wiktionary, the free dictionary. ... Gram-positive anthrax bacteria (purple rods) in cerebrospinal fluid sample. ... Wrights stain is a technique in histology that is used to make the differences between cells visible under light microscopy. ... Jenners Stain (methylene blue eosinate) is used in microscopy for staining blood smears. ... Left: An RNA strand, with its nitrogenous bases. ... The structure of part of a DNA double helix Deoxyribonucleic acid, or DNA, is a nucleic acid molecule that contains the genetic instructions used in the development and functioning of all known living organisms. ... Robert Hookes microscope (1665) - an engineered device used to study living systems. ... The northern blot is a technique used in molecular biology research to study gene expression. ... R-phrases , S-phrases , , , , , Flash point > 100 °C Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Absorption spectrum of ethidium bromide Ethidium bromide (sometimes abbreviated as EtBr) is an intercalating agent commonly used as a nucleic... Intercalation induces structural distortions. ...

It can also be used as an indicator to determine if a cell such as yeast is alive or not. The blue indicator turns colourless in the presence of active enzymes, thus indicating living cells. However if it stays blue it doesn't mean that the cell is dead - the enzymes could be inactive/denatured. It must be noted that methylene blue can inhibit the respiration of the yeast as it picks up hydrogen ions made during the process. The yeast cell cannot then use those ions to release energy.

In neuroscience, methylene blue can also serve as a non-selective inhibitor of NO synthase. The nitric oxide synthases (NOS) are a group of enzymes (EC 1. ...

Medicine

Owing to its reducing agent properties, methylene blue is employed as a medication for the treatment of methemoglobinemia, which can arise from ingestion of certain pharmaceuticals or broad beans. Basically, methylene blue acts to reduce the heme group from methemoglobin to hemoglobin. Methylene blue also blocks accumulation of cyclic guanosine monophosphate (cGMP) by inhibiting the enzyme guanylate cyclase: this action results in reduced responsiveness of vessels to cGMP-dependent vasodilators like nitric oxide and carbon monoxide. Methemoglobinemia, also known as met-Hb, is a disorder characterized by the presence of a higher than normal level of methemoglobin in the blood. ... Binomial name L. Vicia faba, the broad bean, fava bean, faba bean, horse bean, field bean, tic bean, or foul is a species of bean (Fabaceae) native to north Africa and southwest Asia, and extensively cultivated elsewhere. ... Structure of Heme b A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. ... Methemoglobin (also hemiglobin) is a type of hemoglobin that is produced by the oxidation of the ferrous iron contained in hemoglobin to ferric iron which doesnt have the capacity for carrying oxygen. ... Structure of hemoglobin. ... Cyclic guanosine monophosphate (cGMP) is a second messenger derived from GTP. Cyclic guanosine monophosphate (cGMP) is a cyclic nucleotide derived from guanosine triphosphate (GTP). ... Guanylate cyclase (EC 4. ... A vasodilator is a drug or chemical that relaxes the smooth muscle in blood vessels, which causes them to dilate. ... R-phrases , , , , S-phrases , , , Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Nitric oxide or Nitrogen monoxide is a chemical compound with chemical formula NO. This gas is an important signaling molecule in the body of... Carbon monoxide, with the chemical formula CO, is a colorless, odorless, and tasteless gas. ...

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. Colonoscopy is the minimally invasive endoscopic examination of the large colon and the distal part of the small bowel with a CCD camera or a fiber optic camera on a flexible tube passed through the anus. ... Polyp of sigmoid colon as revealed by colonoscopy. ... Saline may refer to: Salinity Saline (medicine) Saline, Michigan Saline, Scotland - a village in the burgh of Fife, Scotland. ... Adrenaline redirects here. ... Endoscopic images of a duodenal ulcer A flexible endoscope. ... Gut redirects here. ... Dysplasia (from Greek, roughly: bad form) is a term used in pathology to refer to an abnormality in maturation of cells within a tissue. ...

Methylene blue was used at the end of the century as a successful treatment for malaria. It disappeared as an anti-malarial during the wars in Asia, as U.S. soldiers disliked its two inevitable, fully reversible side effects: green urine and blue sclera. Interest in its use has recently been revived,^[1] especially because it is very cheap. Several clinical trials are in progress, trying to find a suitable drug combination. Initial attempts to combine methylene blue with chloroquine were disappointing;^[2] however, more recent attempts have appeared more promising. Malaria is a vector-borne infectious disease caused by protozoan parasites. ... This article is about the urine of animals generally. ... Schematic diagram of the human eye. ... Chloroquine is a 4-aminoquinoline drug long used in the treatment or prevention of malaria. ...

In surgeries such as sentinel lymph node dissections, methylene blue can be used to visually trace the lymphatic drainage of pertinent 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. The sentinel lymph node is the hypothetical first lymph node reached by metastasizing cancer cells from a tumor. ... This article or section does not cite its references or sources. ...

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 M. Brooks in San Francisco.^[3] Methylene blue was also used at mid-century in the treatment of carbon monoxide poisoning.^[3] The Electron Transport Chain. ... Potassium cyanide is the inorganic compound with the formula KCN. This colorless crystalline compound, similar in appearance to sugar, is highly soluble in water. ... Carbon monoxide, with the chemical formula CO, is a colorless, odorless, and tasteless gas. ...

Methylene blue is probably a monoamine oxidase inhibitor, 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).^[4] MAOI redirects here. ... Serotonin syndrome is a rare, but potentially life-threatening adverse drug reaction that results from intentional self-poisoning, therapeutic drug use, or inadvertent interactions between drugs. ... Selective serotonin reuptake inhibitors (SSRIs) are a class of antidepressants. ... Duloxetine (brand names Cymbalta, Yentreve, and in parts of Europe, Xeristar or Ariclaim) is a drug which primarily targets major depressive disorder (MDD), generalized anxiety disorder (GAD), pain related to diabetic peripheral neuropathy and in some countries stress urinary incontinence (SUI). ... Sibutramine (Meridia® in the USA, Reductil® in Europe), usually as sibutramide hydrochloride monohydrate, is an orally administered agent for the treatment of obesity. ... Venlafaxine (Effexor) is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class first introduced by Wyeth in 1993. ... Clomipramine (brand-name Anafranil®) is a tricyclic antidepressant. ... This article does not cite any references or sources. ...

Another, less well-known use of methylene blue is its utility for treating ifosfamide neurotoxicity. Methylene blue was first reported for treatment and prophylaxis of ifosfamide neuropsychiatric toxicity in 1994. A toxic metabolite of ifosfamide, chloracetaldehyde (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.^[5] 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 at 50-60mg up to six doses a day have resulted in improvement of symptoms within 10 minutes to several days.^[6] Alternatively, it has been suggested that intravenous methylene blue 50mg every six hours for prophylaxis during ifosfamide treatment in patients with history of ifosfamide neuropsychiatric toxicity.^[7] Prophylactic administration of 50mg of methylene blue the day before initiation of ifosfamide, and 50mg three times daily during ifosfamide chemotherapy has been recommended to lower the occurrence of ifosfamide neurotoxicity.^[8] Ifosfamide (Mitoxana®) Ifosfamide (pronounced i fos fa mide) is chemotherapy that is given as a treatment for many different types of cancer. ... The electron transfer chain (also called the electron transport chain, or simply electron transport), is a series of protein complexers and lipid messengers spanning the inner mitochondrial membrane that accepts electrons from electron donors such as NADH or succinate, shuttles these electrons from within the mitochondrial matrix across the inner... Nicotinamide adenine dinucleotide (NAD+ or in older notation DPN+) is an important coenzyme found in cells. ... Pyruvic acid Oxaloacetic acid Phosphoenolpyruvate Fructose 1,6-bisphosphate Fructose 6-phosphate Glucose-6-phosphate Glucose Gluconeogenesis is the generation of glucose from non-sugar carbon substrates like pyruvate, lactate, glycerol, and amino acids (primarily alanine and glutamine). ...

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, the parasitic protozoa Ichthyophthirius multifiliis. Workers harvest catfish from the Delta Pride Catfish farms in Mississippi Aquaculture is the cultivation of aquatic organisms. ... Leishmania donovani, (a species of protozoan) in a bone marrow cell (in Greek proto = first and zoa = animals) are one-celled eukaryotes (that is, unicellular microbes whose cells have membrane-bound nuclei) that commonly show characteristics usually associated with animals, mobility and heterotrophy. ... Wikimedia Commons has media related to: Ichthyophthirius Ichthyophthirius multifiliis is a species of ciliate protozoa which parasitizes freshwater fish. ...

Pranks

The factual accuracy of this section is disputed. Please see the relevant discussion on the talk page

Methylene blue is highly stable in the human body, and if ingested, it resists the acidic environment of the stomach as well as the many hydrolytic enzymes present. It is not significantly metabolized by the liver, and is instead quickly filtered out by the kidneys. A common prank among chemists and biochemists of the early and middle 20th century was to add small amounts of methylene blue (generally a few drops of a stain solution sufficed) to coffee, cola, or another dark beverage.^{[citation needed]} The stain's color was masked by the beverage, and its taste is fairly faint. Within a few hours, the methylene blue was removed by the prank victim's kidneys, which caused his or her urine to change color^[9] The urine may become green if little methylene blue was added; larger amounts create a deep blue color. The prank is fairly harmless if small amounts of methylene blue are used. Image File history File links Emblem-important. ...

An episode of M*A*S*H, "Sons and Bowlers", showed Major Winchester using a dose of methylene blue to take down a rival camp's bowling champion during a contest. The champ panics when his urine turns blue, and listens to Winchester's advice to refrain from all exercise – including bowling, which allows the 4077th to win. M*A*S*H is an American television series developed by Larry Gelbart, inspired by the 1968 novel M*A*S*H: A Novel About Three Army Doctors by Richard Hooker (penname for H. Richard Hornberger) and its sequels, but primarily by the 1970 film MASH, and influenced by the... Major Charles Emerson Winchester III is a principal character on the television series, M*A*S*H, played by David Ogden Stiers. ... A bowler releases the ball. ...

Adverse Reactions

^[10][11] For other forms of hypertension, see Hypertension (disambiguation). ... This article discusses the medical condition. ...

References

1. ^ Schirmer H, Coulibaly B, Stich A, et al. (2003). "Methylene blue as an antimalarial agent—past and future". Redox Rep. 8: 272–76. doi:10.1179/135100003225002899. 
2. ^ Meissner PE, Mandi G, Coulibaly B, et al. (2006). "Methylene blue for malaria in Africa: results from a dose-finding study in combination with chloroquine". Malaria Journal 5: 84. doi:10.1186/1475-2875-5-84. 
3. ^ ^{a b} Matilda Moldenhauer Brooks (1936). "Methylene Blue as an Antidote for Cyanide and Carbon Monoxide Poisoning". The Scientific Monthly 43 (6): 585-586. 
4. ^ Gillman PK. (2006). "Methylene Blue implicated in potentially fatal serotonin toxicity". Anaesthesia 61: 1013-14. doi:10.1111/j.1365-2044.2006.04808.x. 
5. ^ Yesne AE. (2007). "Ifosfamide neuropsychiatric toxicity in patients with cancer". Psychooncology 9999. 
6. ^ Patel PN. (2006). "Methylene blue for management of ifosfamide induced encephalopathy". Ann Pharmacother 40: 266-303. 
7. ^ Dufour C. (2006). "Ifosfamide induced encephalopathy". Arch Pediatr 13: 140-145. 
8. ^ Aeschlimann T. (1996). "nhibition of (mono)amine oxidase activity and prevention of ifosfamide encephalopathy by methylene blue". Drug Metab Dispos 24: 1336-1339. 
9. ^ Medical use with side effects indicating blue urine. Medicinenet.com.
10. ^ Mokhlesi B. (2003). "Adult Toxicology in Critical Care: Part II: Specific Poisonings". Chest 123: 897. 
11. ^ Harvey JW. (1983). "Studies of the Efficacy and Potential Hazards of Methylene Blue Therapy in Aniline-Induced Methaemoglobinaemia". Br J Haemotol 54: 29. 

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See also

• Prussian blue
• Gentian violet
• Fluorescein

A sample of Prussian blue Prussian blue (German: Preußischblau or Berliner Blau, in English Berlin blue) is a dark blue pigment used in paints and formerly in blueprints. ... Methyl Violet 10B Gentian violet (crystal violet, Methyl Violet 10B, hexamethyl pararosaniline chloride) is an antifungal agent. ... Fluorescein is a fluorophore commonly used in microscopy, in a type of dye laser as the gain medium, in forensics and serology to detect latent blood stains, and in dye tracing. ...

External links

• ATSDR - Methylene Blue
• NIH - Methylene blue test