| Methylene blue | |
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| 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. 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 They are also referred to [Cl-] |
| Properties | |
| Molecular formula | C16H18N3ClS |
| Molar mass | 319. A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 85 g/mol |
| Melting point | 100-110 °C (with decomposion) |
| Boiling point | Decomposes |
| 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. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Sulfur or sulphur (ˈsʌlfɚ see spelling below) is the Chemical element that has the Atomic number 16 It has many uses in a range of different fields, such as biology or chemistry. Foundations of modern biology There are five unifying principles Chemistry (from Egyptian kēme (chem meaning "earth") is the Science concerned with the composition structure and properties At room temperature it appears as a solid, odorless, dark green powder, that yields a blue solution when dissolved in water. Water ( H2[[oxygen O]] H OH) is the most abundant Molecule on Earth 's surface composing of about 70% of the Earth's surface as 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. Methyl blue, also known as Cotton blue, Helvetia blue, Acid blue 93, or C Histology (from the Greek = 'tissue' is the study of the microscopic anatomy of cells and tissues of Plants and New methylene blue (also NMB) is an organic staining agent used in diagnostic Cytology and Histopathology, typically for staining Methyl violet is the name given to a group of similar Chemicals used as PH indicators and Dyes Methyl violets are mixtures of tetramethyl pentamethyl and A pH indicator is a halochromic chemical compound that is added in small amounts to a Solution so that the PH ( Acidity or
Contents |
Uses
Chemistry
Methylene blue is widely used as a redox indicator in analytical chemistry. A redox indicator (also called an oxidation-reduction indicator) is an Indicator that undergoes a definite color change at a specific Electrode potential Analytical chemistry is the study of the Chemical composition of natural and artificial Materials. 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. Chemical kinetics, also known as reaction kinetics is the study of rates of chemical processes Typically, a solution is made of dextrose, methylene blue, and sodium hydroxide. Glucose (Glc a Monosaccharide (or simple Sugar) also known as grape sugar, is an important Carbohydrate in Biology. Sodium hydroxide ( Na[[hydroxide OH]]) also known as Lye, caustic soda and (incorrectly according to IUPAC nomenclature Upon shaking the bottle, oxygen oxidizes methylene blue, and the solution turns blue. Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the 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. Fehling's solution is a Solution used to differentiate between water soluble Aldehyde and Ketone Functional groups although Ketose
Biology
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. A dye can generally be described as a Colored substance that has an affinity to the substrate to which it is being applied Wright's stain is a Histologic stain that facilitates the differentiation of Blood cell types Jenner's Stain ( Methylene blue eosinate) is used in Microscopy for Staining Blood smears 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. Ribonucleic acid ( RNA) is a Nucleic acid that consists of a long chain of Nucleotide units Deoxyribonucleic acid ( DNA) is a Nucleic acid that contains the genetic instructions used in the development and functioning of all known A microscope ( Greek: ( micron) = small + ( skopein) = to look or see is an instrument for viewing objects that are The northern blot is a technique used in Molecular biology research to study Gene expression. 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. Ethidium bromide (sometimes abbreviated as "EtBr", the abbreviation also confusingly used for Bromoethane) is an intercalating agent In Chemistry, intercalation is the reversible inclusion of a Molecule (or group between two other molecules (or groups
It can also be used as an indicator to determine if a cell such as yeast is alive or not. The blue indicator turns colorless 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. Nitric oxide synthases ((NOSs are present among Eukaryotic enzymes as dimeric calmodulin-dependent or calmodulin-containing Cytochrome p450 -like Hemoprotein that
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. Methemoglobinemia is a disorder characterized by the presence of a higher than normal level of Methemoglobin (metHb in the Blood. Vicia faba, the broad bean, fava bean, faba bean, horse bean, field bean, tic bean is a species of Basically, methylene blue acts to reduce the heme group from methemoglobin to hemoglobin. A heme ( American English) or haem ( British English) is a Prosthetic group that consists of an Iron atom contained in the center of Methemoglobin (British English Methaemoglobin (pronounced "MET-hemoglobin" is a form of the Oxygen -carrying Protein Hemoglobin (British English Hemoglobin ( also spelled haemoglobin and abbreviated Hb or Hgb) is the Iron -containing Oxygen -transport Metalloprotein 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. Cyclic guanosine monophosphate ( cGMP) is a Cyclic nucleotide derived from Guanosine triphosphate (GTP Guanylate cyclase ( also known as guanylyl cyclase or GC) is a Lyase Enzyme. Nitric oxide or nitrogen monoxide is a Chemical compound with Chemical formula N[[Oxygen O]] Carbon monoxide, with the chemical formula CO is a colorless odorless tasteless yet highly toxic 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. Colonoscopy is the endoscopic examination of the large colon and the distal part of the small bowel with a CCD camera or a Fiber optic A polyp is an abnormal growth of tissue ( Tumor) projecting from a Mucous membrane. 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. Endoscopy means looking inside and typically refers to looking inside the body for medical reasons using an instrument called an endoscope. Dysplasia (from Greek roughly "bad formation" 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. Malaria is a vector -borne Infectious disease caused by Protozoan Parasites It is widespread in tropical and subtropical regions including 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. Urine is a liquid waste product of the body secreted by the Kidneys by a process of filtration from Blood and Excreted through the Urethra. The sclera, called the white or white of the eye, is the opaque (usually white though certain animals such as horses and lizards can have black sclera fibrous 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. Chloroquine is a 4-aminoquinoline drug 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. The sentinel lymph node is the hypothetical first Lymph node or group of nodes reached by metastasizing Cancer cells from a Tumor. Similarly, methylene blue is added to bone cement in orthopedic operations to provide easy discrimination between native bone and cement. Poly(methyl methacrylate ( PMMA) or poly(methyl 2-methylpropenoate is a Thermoplastic and transparent Plastic. Additionally, methylene blue accelerates the hardening of bone cement, increasing the speed at which bone cement can be effectively applied.
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. An electron transport chain couples a chemical reaction between an electron donor (such as NADH) and an electron acceptor (such as O2) to the transfer Potassium cyanide is an Inorganic compound with the formula KCN Matilda M. Brooks in San Francisco. [3] Methylene blue was also used at mid-century in the treatment of carbon monoxide poisoning. Carbon monoxide, with the chemical formula CO is a colorless odorless tasteless yet highly toxic Gas. [3]
Methylene blue is a monoamine oxidase inhibitor,[4] 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. Monoamine oxidase inhibitors ( MAOIs) are a class of powerful antidepressant drugs prescribed for the treatment of depression. Serotonin syndrome is a potentially life-threatening adverse drug reaction that may occur following therapeutic drug use inadvertent interactions between drugs or the recreational Selective serotonin reuptake inhibitors ( SSRIs) are a class of Antidepressants used in the treatment of depression, Anxiety disorders g. , duloxetine, sibutramine, venlafaxine, clomipramine, imipramine). Duloxetine (brand names Cymbalta, Yentreve) is a Serotonin-norepinephrine reuptake inhibitor (SNRI used for Major depressive disorder (MDD Sibutramine (trade name Meridia in the US and Canada Reductil in Europe and most other countries usually as sibutramine hydrochloride monohydrate is an orally Venlafaxine (Effexor Efexor 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. Imipramine (sold as Antideprin, Deprenil, Deprimin, Deprinol, Depsonil, Dynaprin, Eupramin, Imipramil [5]
Another, less well-known use of methylene blue is its utility for treating ifosfamide neurotoxicity. Ifosfamide (pronounced eyefos'famide (also marketed as Mitoxana and Ifex) is a Nitrogen mustard alkylating agent used in 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). An electron transport chain couples a chemical reaction between an electron donor (such as NADH) and an electron acceptor (such as O2) to the transfer Nicotinamide adenine dinucleotide, abbreviated NAD+, is a Coenzyme found in all living cells The compound is a dinucleotide since it consists 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. Gluconeogenesis (abreviated GNG) is a Metabolic pathway that results in the generation of Glucose from non- Carbohydrate carbon substrates such [6] 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. [7] 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. [8] 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. [9]
Aquaculture
Methylene blue is used in aquaculture and by tropical fish hobbyists as a treatment for fungal infections. Aquaculture is the farming of freshwater and saltwater organisms including Molluscs Crustaceans and aquatic plants It can also be effective in treating fish infected with ich, the parasitic protozoa Ichthyophthirius multifiliis. Protozoa (in Greek πρῶτον proton "first" and ζῷα zoia "animals" are unicellular Eukaryotes (singular Ichthyophthirius multifiliis is a species of Ciliate protozoan which parasitizes freshwater fish the disease it causes is usually called ich
As a Prank on TV
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. M*A*S*H was a Medical drama / Black comedy produced by 20th Television Fox for CBS. Major Charles Emerson Winchester III is a fictional character a principal on the Television series, M*A*S*H, played by David Ogden Stiers. Bowling is a Game / Sport in which players attempt to score points by rolling a Bowling ball along a flat surface either into objects called pins 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. In an episode of "ER" from the 5th season they use it to play a Aprils fools day prank on the desk clerk Jerry. Small methylene blue amounts cause faint green or blue colors; larger amounts cause a deeper blue color. [10] It is not known if this prank is realistic because of the bitterness and color that will be added to the drink.
Methylene blue has been used as a placebo. Placebo is a substance or procedure a patient accepts as medicine or therapy but which has no specific therapeutic activity [11]
Adverse Reactions
| Cardiovascular | Central Nervous System | Dematologic | Gastrointestinal | Genitourinary | 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 •Bladder irritation | •Anemia |
References
- ^ Schirmer H, Coulibaly B, Stich A, et al. Hypertension, also referred to as high blood pressure, HTN or HPN, is a medical condition in which the Blood pressure is chronically elevated Anemia ( AmE) or anæmia/anaemia ( BrE) (from the Ancient Greek grc-Latn anaîmia, meaning “without blood” is defined as a qualitative (2003). "Methylene blue as an antimalarial agent—past and future". Redox Rep. 8: 272–76. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ 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:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ a b Matilda Moldenhauer Brooks (1936). "Methylene Blue as an Antidote for Cyanide and Carbon Monoxide Poisoning". The Scientific Monthly 43 (6): 585-586.
- ^ Gillman PK (May 2008). "Methylene blue is a potent monoamine oxidase inhibitor". Can J Anaesth 55 (5): 311–2. PMID 18451123.
- ^ Gillman PK. (2006). "Methylene Blue implicated in potentially fatal serotonin toxicity". Anaesthesia 61: 1013-14. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ Alici-Evcimen Y, Breitbart WS (October 2007). "Ifosfamide neuropsychiatric toxicity in patients with cancer". Psychooncology 16 (10): 956–60. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 17278152.
- ^ Patel PN. (2006). "Methylene blue for management of ifosfamide induced encephalopathy". Ann Pharmacother 40: 266-303. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ Dufour C, Grill J, Sabouraud P, et al (February 2006). "[Ifosfamide induced encephalopathy: 15 observations]" (in French). Arch Pediatr 13 (2): 140–5. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 16364615.
- ^ Aeschlimann T. (1996). "Inhibition of (mono)amine oxidase activity and prevention of ifosfamide encephalopathy by methylene blue". Drug Metab Dispos 24: 1336-1339.
- ^ Medical use with side effects indicating blue urine. Medicinenet. com.
- ^ Steve Novella. Steven P Novella is an American clinical neurologist, assistant professor and Director of General Neurology at Yale University School of Medicine. The Ethics of Deception in Medicine. Science Based Medicine. Retrieved on 2008-01-24. 2008 ( MMVIII) is the current year in accordance with the Gregorian calendar, a Leap year that started on Tuesday of the Common Events 41 - Gaius Caesar (Caligula, known for his eccentricity and cruel Despotism, is Assassinated by his disgruntled
- ^ Mokhlesi B. (2003). "Adult Toxicology in Critical Care: Part II: Specific Poisonings". Chest 123: 897.
- ^ Harvey JW. (1983). "Studies of the Efficacy and Potential Hazards of Methylene Blue Therapy in Aniline-Induced Methaemoglobinaemia". Br J Haemotol 54: 29. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
See also
External links
Prussian blue is a very dark blue colorfast non-toxic Pigment – one of the first synthetic Dyes – which was discovered accidentally in Berlin in 1704 Gentian violet ( Crystal violet, Methyl Violet 10B, hexamethyl Pararosaniline chloride is an antifungal agent,the primary agent used in the Fluorescein is a Fluorophore commonly used in Microscopy, in a type of Dye laser as the Gain medium, in Forensics and SerologyDapyx Software network: MP3 Explorer | Ebook Manager | Zenithic