Difference between revisions of "Methylene blue"
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'''Methylene blue''' is a [[Heterocyclic ring|heterocyclic]] [[aromaticity|aromatic]] [[chemical compound]] with the [[molecular formula]] [[carbon|C]]<sub>16</sub>[[hydrogen|H]]<sub>18</sub>[[nitrogen|N]]<sub>3</sub>[[sulfur|S]][[chlorine|Cl]]. It has many uses in a range of different fields, such as [[biology]] and [[chemistry]]. At room temperature it appears as a solid, odorless, dark green powder, that yields a blue solution when dissolved in [[water (molecule)|water]]. The hydrated form has 3 molecules of water per molecule of MB.<ref>http://www.methylene-blue.com/substance.php</ref> Methylene blue should not be confused with [[methyl blue]], another [[histology]] stain, [[new methylene blue]], nor with the [[methyl violet]]s often used as [[pH indicator]]s. | '''Methylene blue''' is a [[Heterocyclic ring|heterocyclic]] [[aromaticity|aromatic]] [[chemical compound]] with the [[molecular formula]] [[carbon|C]]<sub>16</sub>[[hydrogen|H]]<sub>18</sub>[[nitrogen|N]]<sub>3</sub>[[sulfur|S]][[chlorine|Cl]]. It has many uses in a range of different fields, such as [[biology]] and [[chemistry]]. At room temperature it appears as a solid, odorless, dark green powder, that yields a blue solution when dissolved in [[water (molecule)|water]]. The hydrated form has 3 molecules of water per molecule of MB.<ref>http://www.methylene-blue.com/substance.php</ref> Methylene blue should not be confused with [[methyl blue]], another [[histology]] stain, [[new methylene blue]], nor with the [[methyl violet]]s often used as [[pH indicator]]s. | ||
| − | The | + | The [[International Nonproprietary Name]] (INN) of methylene blue is '''methylthioninium chloride'''.<ref name="pmid18037845">{{Cite journal|author=Adams V, Marley J, McCarroll C |title=Prilocaine induced methaemoglobinaemia in a medically compromised patient. Was this an inevitable consequence of the dose administered? |journal=Br Dent J |volume=203 |issue=10 |pages=585–7 |year=2007 |month=November |pmid=18037845 |doi=10.1038/bdj.2007.1045}}</ref><ref name="pmid16688009">{{Cite journal|author=Linz AJ, Greenham RK, Fallon LF |title=Methemoglobinemia: an industrial outbreak among rubber molding workers |journal=J. Occup. Environ. Med. |volume=48 |issue=5 |pages=523–8 |year=2006 |month=May |pmid=16688009 |doi=10.1097/01.jom.0000201815.32098.99 |url=http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?an=00043764-200605000-00010}}</ref> |
==Uses== | ==Uses== | ||
| Line 37: | Line 37: | ||
====Sulfide analysis==== | ====Sulfide analysis==== | ||
| − | The formation of methylene blue after the reaction of [[hydrogen sulfide]] with [[dimethyl-p-phenylenediamine]] and [[Ferric|iron(III)]] at pH 0.4 – 0.7 is used to determine by [[Ultraviolet-visible spectroscopy|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<sub>2</sub>S is stable for 60 min. Ready-to-use kits such as the ''Spectroquant'' [[sulfide]] test<ref>[http://photometry.merck.de/ Spectroquant 114779 Sulfide Test. Method: photometric 0.020 - 1.50 mg/l S<sup>2-</sup>]</ref> 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 must be well noted that in this test, methylene blue is a product of reaction and not a reagent. | + | The formation of methylene blue after the reaction of [[hydrogen sulfide]] with [[dimethyl-p-phenylenediamine]] and [[Ferric|iron(III)]] at pH 0.4 – 0.7 is used to determine by [[Ultraviolet-visible spectroscopy|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<sub>2</sub>S is stable for 60 min. Ready-to-use kits such as the ''Spectroquant'' [[sulfide]] test<ref>[http://photometry.merck.de/ Spectroquant 114779 Sulfide Test. Method: photometric 0.020 - 1.50 mg/l S<sup>2-</sup>]</ref> 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 must be{{Citation needed|date=September 2010}} well noted 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. | 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. | ||
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===Medicine=== | ===Medicine=== | ||
Methylene blue is a [[monoamine oxidase inhibitor]] (MAOI),<ref> | Methylene blue is a [[monoamine oxidase inhibitor]] (MAOI),<ref> | ||
| − | {{ | + | {{Cite journal |
|author=Gillman PK | |author=Gillman PK | ||
|title=Methylene blue is a potent monoamine oxidase inhibitor | |title=Methylene blue is a potent monoamine oxidase inhibitor | ||
| Line 67: | Line 67: | ||
|last4=Liang | |last4=Liang | ||
|first4=Rhea W. Y. | |first4=Rhea W. Y. | ||
| − | }}</ref> 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]]).<ref name="pmid16978328">{{ | + | }}</ref> 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]]).<ref name="pmid16978328">{{Cite journal |
| author = Gillman PK | | author = Gillman PK | ||
| title = Methylene blue implicated in potentially fatal serotonin toxicity | | title = Methylene blue implicated in potentially fatal serotonin toxicity | ||
| Line 78: | Line 78: | ||
| pmid = 16978328 | | pmid = 16978328 | ||
| doi = 10.1111/j.1365-2044.2006.04808.x | | doi = 10.1111/j.1365-2044.2006.04808.x | ||
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
}}</ref> | }}</ref> | ||
| − | Methylene blue is also structurally similar to the [[chlorpromazine]] and the [[typical antipsychotics]]. It is the basic compound from which chlorpromazine and many other antipsychotics are made.<ref>{{ | + | Methylene blue is also structurally similar to the [[chlorpromazine]] and the [[typical antipsychotics]]. It is the basic compound from which chlorpromazine and many other antipsychotics are made.<ref>{{Cite book |
|last = Healy | |last = Healy | ||
|first = David | |first = David | ||
| − | |authorlink = David Healy | + | |authorlink = David Healy (psychiatrist) |
|title = The Creation of Psychopharmacology | |title = The Creation of Psychopharmacology | ||
|publisher = [[Harvard University Press]] | |publisher = [[Harvard University Press]] | ||
|year = 2002 | |year = 2002 | ||
|isbn = 0674006194}}</ref> | |isbn = 0674006194}}</ref> | ||
| + | |||
====Malaria==== | ====Malaria==== | ||
Methylene blue was identified by [[Paul Ehrlich]] about 1891 as a successful 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]] green, and the [[sclera]] (the whites of the eyes) blue. Interest in its use as an anti-malarial has recently been revived,<ref> | Methylene blue was identified by [[Paul Ehrlich]] about 1891 as a successful 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]] green, and the [[sclera]] (the whites of the eyes) blue. Interest in its use as an anti-malarial has recently been revived,<ref> | ||
| − | {{ | + | {{Cite journal |
| author=Schirmer H, Coulibaly B, Stich A, ''et al.'' | | author=Schirmer H, Coulibaly B, Stich A, ''et al.'' | ||
| title=Methylene blue as an antimalarial agent—past and future | | title=Methylene blue as an antimalarial agent—past and future | ||
| Line 103: | Line 104: | ||
| issue=5 | | issue=5 | ||
}}</ref> especially due to its low price. Several clinical trials are in progress, trying to find a suitable drug combination. Initial attempts to combine methylene blue with [[chloroquine]] were disappointing;<ref> | }}</ref> especially due to its low price. Several clinical trials are in progress, trying to find a suitable drug combination. Initial attempts to combine methylene blue with [[chloroquine]] were disappointing;<ref> | ||
| − | {{ | + | {{Cite journal |
| − | | title=Methylene blue for malaria in Africa: results from a dose-finding study in combination with chloroquine | + | | title=Methylene blue for malaria in Africa: results from a dose-finding study in combination with chloroquine |
| author=Meissner PE, Mandi G, Coulibaly B, ''et al.'' | | author=Meissner PE, Mandi G, Coulibaly B, ''et al.'' | ||
| journal=Malaria Journal | | journal=Malaria Journal | ||
| Line 119: | Line 120: | ||
====Combined with light==== | ====Combined with light==== | ||
| − | Methylene blue combined with light has been used to treat resistant plaque psoriasis,<ref name="pmid19180895">{{ | + | Methylene blue combined with light has been used to treat resistant plaque psoriasis,<ref name="pmid19180895">{{Cite journal |
| author = Salah M, Samy N, Fadel M | | author = Salah M, Samy N, Fadel M | ||
| title = Methylene blue mediated photodynamic therapy for resistant plaque psoriasis | | title = Methylene blue mediated photodynamic therapy for resistant plaque psoriasis | ||
| Line 129: | Line 130: | ||
| month = January | | month = January | ||
| pmid = 19180895 | | pmid = 19180895 | ||
| − | | doi = | + | | doi = |
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
| − | }}</ref> AIDS-related Kaposi's sarcoma,<ref name="pmid16942436">{{ | + | }}</ref> AIDS-related Kaposi's sarcoma,<ref name="pmid16942436">{{Cite journal |
| author = Tardivo JP, Del Giglio A, Paschoal LH, Baptista MS | | author = Tardivo JP, Del Giglio A, Paschoal LH, Baptista MS | ||
| title = New photodynamic therapy protocol to treat AIDS-related Kaposi's sarcoma | | title = New photodynamic therapy protocol to treat AIDS-related Kaposi's sarcoma | ||
| Line 143: | Line 144: | ||
| pmid = 16942436 | | pmid = 16942436 | ||
| doi = 10.1089/pho.2006.24.528 | | doi = 10.1089/pho.2006.24.528 | ||
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
| − | }}</ref> West Nile virus,<ref name="pmid16118025">{{ | + | }}</ref> West Nile virus,<ref name="pmid16118025">{{Cite journal |
| author = Papin JF, Floyd RA, Dittmer DP | | author = Papin JF, Floyd RA, Dittmer DP | ||
| title = Methylene blue photoinactivation abolishes West Nile virus infectivity in vivo | | title = Methylene blue photoinactivation abolishes West Nile virus infectivity in vivo | ||
| Line 156: | Line 157: | ||
| pmid = 16118025 | | pmid = 16118025 | ||
| doi = 10.1016/j.antiviral.2005.07.001 | | doi = 10.1016/j.antiviral.2005.07.001 | ||
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
| − | }}</ref> and to inactivate staphylococcus aureus,<ref name="pmid19193212">{{ | + | }}</ref> and to inactivate staphylococcus aureus,<ref name="pmid19193212">{{Cite journal |
| author = Zolfaghari PS, Packer S, Singer M, Nair SP, Bennett J, Street C, Wilson M | | author = Zolfaghari PS, Packer S, Singer M, Nair SP, Bennett J, Street C, Wilson M | ||
| title = In vivo killing of Staphylococcus aureus using a light-activated antimicrobial agent | | title = In vivo killing of Staphylococcus aureus using a light-activated antimicrobial agent | ||
| journal = [[BMC Microbiol.]] | | journal = [[BMC Microbiol.]] | ||
| volume = 9 | | volume = 9 | ||
| − | | issue = | + | | issue = |
| pages = 27 | | pages = 27 | ||
| year = 2009 | | year = 2009 | ||
| Line 169: | Line 170: | ||
| pmc = 2642833 | | pmc = 2642833 | ||
| doi = 10.1186/1471-2180-9-27 | | doi = 10.1186/1471-2180-9-27 | ||
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
| − | }}</ref> HIV-1,<ref name="pmid15168794">{{ | + | }}</ref> HIV-1,<ref name="pmid15168794">{{Cite journal |
| author = Floyd RA, Schneider JE, Dittmer DP | | author = Floyd RA, Schneider JE, Dittmer DP | ||
| title = Methylene blue photoinactivation of RNA viruses | | title = Methylene blue photoinactivation of RNA viruses | ||
| Line 182: | Line 183: | ||
| pmid = 15168794 | | pmid = 15168794 | ||
| doi = 10.1016/j.antiviral.2003.11.004 | | doi = 10.1016/j.antiviral.2003.11.004 | ||
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
| − | }}</ref> Duck hepatitis B,<ref name="pmid11552074">{{ | + | }}</ref> Duck hepatitis B,<ref name="pmid11552074">{{Cite journal |
| author = Wagner SJ, Skripchenko A, Pugh JC, Suchmann DB, Ijaz MK | | author = Wagner SJ, Skripchenko A, Pugh JC, Suchmann DB, Ijaz MK | ||
| title = Duck hepatitis B photoinactivation bydimethylmethylene blue in RBC suspensions | | title = Duck hepatitis B photoinactivation bydimethylmethylene blue in RBC suspensions | ||
| − | | journal = [[Transfusion]] | + | | journal = [[Transfusion (journal)|Transfusion]] |
| volume = 41 | | volume = 41 | ||
| issue = 9 | | issue = 9 | ||
| Line 195: | Line 196: | ||
| pmid = 11552074 | | pmid = 11552074 | ||
| doi = 10.1046/j.1537-2995.2001.41091154.x | | doi = 10.1046/j.1537-2995.2001.41091154.x | ||
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
| − | }}</ref> adenovirus vectors,<ref name="pmid10505113">{{ | + | }}</ref> adenovirus vectors,<ref name="pmid10505113">{{Cite journal |
| author = Schagen FH, Moor AC, Cheong SC, Cramer SJ, van Ormondt H, van der Eb AJ, Dubbelman TM, Hoeben RC | | author = Schagen FH, Moor AC, Cheong SC, Cramer SJ, van Ormondt H, van der Eb AJ, Dubbelman TM, Hoeben RC | ||
| title = Photodynamic treatment of adenoviral vectors with visible light: an easy and convenient method for viral inactivation | | title = Photodynamic treatment of adenoviral vectors with visible light: an easy and convenient method for viral inactivation | ||
| Line 208: | Line 209: | ||
| pmid = 10505113 | | pmid = 10505113 | ||
| doi = 10.1038/sj.gt.3300897 | | doi = 10.1038/sj.gt.3300897 | ||
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
| − | }}</ref> and hepatitis C.<ref name="pmid9783692">{{ | + | }}</ref> and hepatitis C.<ref name="pmid9783692">{{Cite journal |
| author = Müller-Breitkreutz K, Mohr H | | author = Müller-Breitkreutz K, Mohr H | ||
| title = Hepatitis C and human immunodeficiency virus RNA degradation by methylene blue/light treatment of human plasma | | title = Hepatitis C and human immunodeficiency virus RNA degradation by methylene blue/light treatment of human plasma | ||
| Line 221: | Line 222: | ||
| pmid = 9783692 | | pmid = 9783692 | ||
| doi = 10.1002/(SICI)1096-9071(199811)56:3<239::AID-JMV11>3.0.CO;2-9 | | doi = 10.1002/(SICI)1096-9071(199811)56:3<239::AID-JMV11>3.0.CO;2-9 | ||
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
| − | }}</ref> Phenothiazine dyes and light have been known to have virucidal properties for over 80 years.<ref name="pmid10794099">{{ | + | }}</ref> Phenothiazine dyes and light have been known to have virucidal properties for over 80 years.<ref name="pmid10794099">{{Cite journal |
| author = Wagner SJ, Skripchenko A, Robinette D, Mallory DA, Hirayama J, Cincotta L, Foley J | | author = Wagner SJ, Skripchenko A, Robinette D, Mallory DA, Hirayama J, Cincotta L, Foley J | ||
| title = The use of dimethylmethylene blue for virus photoinactivation of red cell suspensions | | title = The use of dimethylmethylene blue for virus photoinactivation of red cell suspensions | ||
| journal = [[Dev Biol (Basel)]] | | journal = [[Dev Biol (Basel)]] | ||
| volume = 102 | | volume = 102 | ||
| − | | issue = | + | | issue = |
| pages = 125–9 | | pages = 125–9 | ||
| year = 2000 | | year = 2000 | ||
| pmid = 10794099 | | pmid = 10794099 | ||
| − | | doi = | + | | doi = |
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
| − | }}</ref> In some circumstances, the combination can cause DNA damage that may lead to cancer.<ref name="pmid19218330">{{ | + | }}</ref> In some circumstances, the combination can cause DNA damage that may lead to cancer.<ref name="pmid19218330">{{Cite journal |
| author = Sturmey RG, Wild CP, Hardie LJ | | author = Sturmey RG, Wild CP, Hardie LJ | ||
| title = Removal of red light minimizes methylene blue-stimulated DNA damage in oesophageal cells: implications for chromoendoscopy | | title = Removal of red light minimizes methylene blue-stimulated DNA damage in oesophageal cells: implications for chromoendoscopy | ||
| Line 246: | Line 247: | ||
| pmid = 19218330 | | pmid = 19218330 | ||
| doi = 10.1093/mutage/gep004 | | doi = 10.1093/mutage/gep004 | ||
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
| − | }}</ref><ref name="pmid12907012">{{ | + | }}</ref><ref name="pmid12907012">{{Cite journal |
| author = Olliver JR, Wild CP, Sahay P, Dexter S, Hardie LJ | | author = Olliver JR, Wild CP, Sahay P, Dexter S, Hardie LJ | ||
| title = Chromoendoscopy with methylene blue and associated DNA damage in Barrett's oesophagus | | title = Chromoendoscopy with methylene blue and associated DNA damage in Barrett's oesophagus | ||
| Line 259: | Line 260: | ||
| pmid = 12907012 | | pmid = 12907012 | ||
| doi = 10.1016/S0140-6736(03)14026-3 | | doi = 10.1016/S0140-6736(03)14026-3 | ||
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
| − | }}</ref> | + | }}</ref> |
====Methemoglobinemia==== | ====Methemoglobinemia==== | ||
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====Cyanide poisoning==== | ====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.<ref name = brooks> | 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.<ref name = brooks> | ||
| − | {{ | + | {{Cite journal |
| title = Methylene Blue as an Antidote for Cyanide and Carbon Monoxide Poisoning | | title = Methylene Blue as an Antidote for Cyanide and Carbon Monoxide Poisoning | ||
| author = Matilda Moldenhauer Brooks | | author = Matilda Moldenhauer Brooks | ||
| Line 277: | Line 278: | ||
| pages = 585–586 | | pages = 585–586 | ||
| url =http://links.jstor.org/sici?sici=0096-3771%28193612%2943%3A6%3C585%3AMBAAAF%3E2.0.CO%3B2-%23 | | url =http://links.jstor.org/sici?sici=0096-3771%28193612%2943%3A6%3C585%3AMBAAAF%3E2.0.CO%3B2-%23 | ||
| − | }}</ref> | + | }}</ref> |
====Carbon monoxide poisoning==== | ====Carbon monoxide poisoning==== | ||
| Line 287: | Line 288: | ||
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. | 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. | ||
| − | It can also be used to stain lymph nodes | + | It can also be used to stain lymph nodes. |
====Placebo==== | ====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.<ref>{{ | + | 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.<ref>{{Cite web |
|url= http://www.sciencebasedmedicine.org/?p=29 | |url= http://www.sciencebasedmedicine.org/?p=29 | ||
|title=The Ethics of Deception in Medicine | |title=The Ethics of Deception in Medicine | ||
| Line 298: | Line 299: | ||
|work= Science Based Medicine | |work= Science Based Medicine | ||
|publisher= | |publisher= | ||
| − | }}</ref> This same side effect makes methylene blue difficult to test in traditional placebo-controlled [[clinical studies]].<ref>{{ | + | }}</ref> This same side effect makes methylene blue difficult to test in traditional placebo-controlled [[clinical studies]].<ref>{{Cite web |
|url=http://clinicaltrials.gov/ct2/show/NCT00214877 | |url=http://clinicaltrials.gov/ct2/show/NCT00214877 | ||
|title=Methylene blue for cognitive dysfunction in bipolar disorder | |title=Methylene blue for cognitive dysfunction in bipolar disorder | ||
| Line 308: | Line 309: | ||
====Ifosfamide neurotoxicity==== | ====Ifosfamide neurotoxicity==== | ||
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<ref> | 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<ref> | ||
| − | {{ | + | {{Cite journal|author=Alici-Evcimen Y, Breitbart WS |
|title=Ifosfamide neuropsychiatric toxicity in patients with cancer | |title=Ifosfamide neuropsychiatric toxicity in patients with cancer | ||
|journal=Psychooncology | |journal=Psychooncology | ||
| Line 319: | Line 320: | ||
|doi=10.1002/pon.1161 | |doi=10.1002/pon.1161 | ||
}}</ref> 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 50–60 mg up to six doses a day have resulted in improvement of symptoms within 10 minutes to several days.<ref> | }}</ref> 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 50–60 mg up to six doses a day have resulted in improvement of symptoms within 10 minutes to several days.<ref> | ||
| − | {{ | + | {{Cite journal |
| author=Patel PN | | author=Patel PN | ||
| year=2006 | | year=2006 | ||
| Line 330: | Line 331: | ||
| issue=2 | | issue=2 | ||
}}</ref> Alternatively, it has been suggested that intravenous methylene blue 50 mg every six hours for prophylaxis during ifosfamide treatment in patients with history of ifosfamide neuropsychiatric toxicity.<ref> | }}</ref> Alternatively, it has been suggested that intravenous methylene blue 50 mg every six hours for prophylaxis during ifosfamide treatment in patients with history of ifosfamide neuropsychiatric toxicity.<ref> | ||
| − | {{ | + | {{Cite journal |
|author=Dufour C, Grill J, Sabouraud P, ''et al.'' | |author=Dufour C, Grill J, Sabouraud P, ''et al.'' | ||
|title=Ifosfamide induced encephalopathy: 15 observations | |title=Ifosfamide induced encephalopathy: 15 observations | ||
| Line 341: | Line 342: | ||
|month=February | |month=February | ||
|pmid=16364615 | |pmid=16364615 | ||
| − | |doi=10.1016/j.arcped.2005.10.021 | + | |doi=10.1016/j.arcped.2005.10.021 |
}}</ref> Prophylactic administration of 50 mg of methylene blue the day before initiation of ifosfamide, and 50 mg three times daily during ifosfamide chemotherapy has been recommended to lower the occurrence of ifosfamide neurotoxicity.<ref> | }}</ref> Prophylactic administration of 50 mg of methylene blue the day before initiation of ifosfamide, and 50 mg three times daily during ifosfamide chemotherapy has been recommended to lower the occurrence of ifosfamide neurotoxicity.<ref> | ||
| − | {{ | + | {{Cite journal |
| author=Aeschlimann T | | author=Aeschlimann T | ||
| year=1996 | | year=1996 | ||
| Line 360: | Line 361: | ||
====Clinical trials==== | ====Clinical trials==== | ||
[[TauRx Therapeutics]] has reported that methylene blue (methylthioninium chloride), under the tradename [[rember]], may provide a way of halting or slowing the progression of Alzheimer's dementia.<ref name="BBCNews"> | [[TauRx Therapeutics]] has reported that methylene blue (methylthioninium chloride), under the tradename [[rember]], may provide a way of halting or slowing the progression of Alzheimer's dementia.<ref name="BBCNews"> | ||
| − | {{ | + | {{Cite web |
| url=http://news.bbc.co.uk/1/hi/health/7525115.stm | | url=http://news.bbc.co.uk/1/hi/health/7525115.stm | ||
| title=Alzheimer's drug 'halts' decline | | title=Alzheimer's drug 'halts' decline | ||
| date=2008-07-30 | | date=2008-07-30 | ||
| publisher=[[BBC News]] | | publisher=[[BBC News]] | ||
| − | | accessdate=2008-07-30 | + | | accessdate=2008-07-30 |
}}</ref> However, the formulation used was different from that commonly available as a medicine and caution has been expressed about use of methylene blue as a treatment for Alzheimer's.<ref> | }}</ref> However, the formulation used was different from that commonly available as a medicine and caution has been expressed about use of methylene blue as a treatment for Alzheimer's.<ref> | ||
| − | {{ | + | {{Cite web |
| url=http://www.chicagotribune.com/features/lifestyle/health/chi-alzheimers-wedjul30,0,3112870.story | | url=http://www.chicagotribune.com/features/lifestyle/health/chi-alzheimers-wedjul30,0,3112870.story | ||
| publisher=[[Chicago Tribune]] | | publisher=[[Chicago Tribune]] | ||
| date=2008-07-30 | | date=2008-07-30 | ||
| title=Slowing disease's mental ravages | | title=Slowing disease's mental ravages | ||
| − | }}</ref> TauRx Therapeutics has suggested that the mechanism by which methylene blue might delay or reverse neurodegeneration in Alzheimer's disease is as an inhibitor of Tau protein aggregation. While methylene blue arguably has an effect on Tau aggregation, it also has an effect on mitochondrial function which is likely to play an important role. In vitro studies suggest that methylene blue might be an effective remedy for both Alzheimer's and Parkinson's disease by enhancing key [[mitochondrial]] biochemical pathways. It can disinhibit and increase [[complex IV]], whose inhibition correlates with Alzheimer's disease. | + | }}</ref> TauRx Therapeutics has suggested that the mechanism by which methylene blue might delay or reverse neurodegeneration in Alzheimer's disease is as an inhibitor of Tau protein aggregation. While methylene blue arguably has an effect on Tau aggregation, it also has an effect on mitochondrial function which is likely to play an important role. In vitro studies suggest that methylene blue might be an effective remedy for both Alzheimer's and Parkinson's disease by enhancing key [[mitochondrial]] biochemical pathways. It can disinhibit and increase [[complex IV]], whose inhibition correlates with Alzheimer's disease. |
Methylene blue might also delay [[senescence]] as one study has shown that it extended the lifespan of [[IMR90]] fibroblasts by more than 20 population doublings.<ref> | Methylene blue might also delay [[senescence]] as one study has shown that it extended the lifespan of [[IMR90]] fibroblasts by more than 20 population doublings.<ref> | ||
| − | {{ | + | {{Cite journal |
|author=Atamna H, Nguyen A, Schultz C, Boyle K, Newberry J, Kato H, Ames BN | |author=Atamna H, Nguyen A, Schultz C, Boyle K, Newberry J, Kato H, Ames BN | ||
|title=Methylene blue delays cellular senescence and enhances key mitochondrial biochemical pathways | |title=Methylene blue delays cellular senescence and enhances key mitochondrial biochemical pathways | ||
| Line 392: | Line 393: | ||
===Aquaculture=== | ===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]]''. 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 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]]''. 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"<ref>[http://www.americanaquariumproducts.com/AquariumMedication3.html] Aquarium Chemical Treatments</ref> | + | 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".<ref>[http://www.americanaquariumproducts.com/AquariumMedication3.html] Aquarium Chemical Treatments</ref> |
| − | ===As a prank === | + | ===As a prank=== |
It is, or was at one time, a common prank among college students in biomedical fields to spike someone's drink with methylene blue, thus creating amusement at the victim's expense when he reacts with alarm to his urine turning blue. With concern over date rape drugs, spiking someone's drink is considered far more serious than it used to be, and the prank has somewhat gone out of fashion. | It is, or was at one time, a common prank among college students in biomedical fields to spike someone's drink with methylene blue, thus creating amusement at the victim's expense when he reacts with alarm to his urine turning blue. With concern over date rape drugs, spiking someone's drink is considered far more serious than it used to be, and the prank has somewhat gone out of fashion. | ||
| Line 400: | Line 401: | ||
An episode of ''[[M*A*S*H (TV series)|M*A*S*H]]'', "Sons and Bowlers", showed [[Major Charles Emerson Winchester III|Major Winchester]] using a dose of methylene blue to take down a rival camp's [[bowling]] champion—who had been a high-ranked professional bowler in civilian life—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. In an episode of "ER" from the 5th season they use it to play an [[April Fools' Day]] [[prank]] on the desk clerk Jerry.<ref> | An episode of ''[[M*A*S*H (TV series)|M*A*S*H]]'', "Sons and Bowlers", showed [[Major Charles Emerson Winchester III|Major Winchester]] using a dose of methylene blue to take down a rival camp's [[bowling]] champion—who had been a high-ranked professional bowler in civilian life—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. In an episode of "ER" from the 5th season they use it to play an [[April Fools' Day]] [[prank]] on the desk clerk Jerry.<ref> | ||
| − | {{ | + | {{Cite web |
|url=http://www.medicinenet.com/methylene_blue-oral/article.htm | |url=http://www.medicinenet.com/methylene_blue-oral/article.htm | ||
|title=Medical use with side effects indicating blue urine | |title=Medical use with side effects indicating blue urine | ||
| Line 408: | Line 409: | ||
===Adverse reactions=== | ===Adverse reactions=== | ||
| − | |||
{| class="wikitable" | {| class="wikitable" | ||
|- | |- | ||
| Line 424: | Line 424: | ||
| • Discoloration of [[urine]]<br />• [[Bladder]] irritation | | • Discoloration of [[urine]]<br />• [[Bladder]] irritation | ||
| • [[Anemia]] | | • [[Anemia]] | ||
| − | |}<ref name="pmid12628894">{{ | + | |}<ref name="pmid12628894">{{Cite journal |
| author = Mokhlesi B, Leikin JB, Murray P, Corbridge TC | | author = Mokhlesi B, Leikin JB, Murray P, Corbridge TC | ||
| title = Adult toxicology in critical care: Part II: specific poisonings | | title = Adult toxicology in critical care: Part II: specific poisonings | ||
| Line 435: | Line 435: | ||
| pmid = 12628894 | | pmid = 12628894 | ||
| doi = 10.1378/chest.123.3.897 | | doi = 10.1378/chest.123.3.897 | ||
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
| − | }}</ref><ref name="pmid6849836">{{ | + | }}</ref><ref name="pmid6849836">{{Cite journal |
| author = Harvey JW, Keitt AS | | author = Harvey JW, Keitt AS | ||
| title = Studies of the efficacy and potential hazards of methylene blue therapy in aniline-induced methaemoglobinaemia | | title = Studies of the efficacy and potential hazards of methylene blue therapy in aniline-induced methaemoglobinaemia | ||
| Line 448: | Line 448: | ||
| pmid = 6849836 | | pmid = 6849836 | ||
| doi = 10.1111/j.1365-2141.1983.tb02064.x | | doi = 10.1111/j.1365-2141.1983.tb02064.x | ||
| − | | url = | + | | url = |
| − | | issn = | + | | issn = |
}}</ref> | }}</ref> | ||
Latest revision as of 15:46, 27 September 2010
| Methylene blue | |
|---|---|
| Methylene blue | |
| Space-filling model of methylene blue in its oxidised form | |
| 3,7-bis(Dimethylamino)- phenothiazin-5-ium chloride | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 61-73-4 
|
| PubChem | 6099 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C16H18N3SCl |
| Molar mass | 319.85 g/mol |
| Melting point |
100-110 °C (with decomposition) |
| Boiling point |
Decomposes |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Methylene blue is a heterocyclic aromatic chemical compound with the molecular formula C16H18N3SCl. It has many uses in a range of different fields, such as biology and chemistry. At room temperature it appears as a solid, odorless, dark green powder, that yields a blue solution when dissolved in water. The hydrated form has 3 molecules of water per molecule of MB.[1] 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 International Nonproprietary Name (INN) of methylene blue is methylthioninium chloride.[2][3]
Contents
Uses
Chemistry
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 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.
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 H2S is stable for 60 min. Ready-to-use kits such as the Spectroquant sulfide test[4] 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 must be[citation needed] well noted 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.
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. 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 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.
Medicine
Methylene blue is a monoamine oxidase inhibitor (MAOI),[5] 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).[6]
Methylene blue is also structurally similar to the chlorpromazine and the typical antipsychotics. It is the basic compound from which chlorpromazine and many other antipsychotics are made.[7]
Malaria
Methylene blue was identified by Paul Ehrlich about 1891 as a successful 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 green, and the sclera (the whites of the eyes) blue. Interest in its use as an anti-malarial has recently been revived,[8] especially due to its low price. Several clinical trials are in progress, trying to find a suitable drug combination. Initial attempts to combine methylene blue with chloroquine were disappointing;[9] however, more recent attempts have appeared more promising.
Cancer
Recent research suggests that methylene blue, toluidine blue, and other 3,7-diaminophenothiazinium-based redox cyclers induce selective cancer cell apoptosis by NAD(P)H:quinone oxidoreductase (NQO1)-dependent bioreductive generation of cellular oxidative stress.[10] Combined with plant auxin (indole-3-acetic acid), methylene blue is being investigated for the photodynamic treatment of cancer.[11]
Combined with light
Methylene blue combined with light has been used to treat resistant plaque psoriasis,[12] AIDS-related Kaposi's sarcoma,[13] West Nile virus,[14] and to inactivate staphylococcus aureus,[15] HIV-1,[16] Duck hepatitis B,[17] adenovirus vectors,[18] and hepatitis C.[19] Phenothiazine dyes and light have been known to have virucidal properties for over 80 years.[20] In some circumstances, the combination can cause DNA damage that may lead to cancer.[21][22]
Methemoglobinemia
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[citation needed]. 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.
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.[23]
Carbon monoxide poisoning
Methylene blue was also used in the mid-twentieth century in the treatment of carbon monoxide poisoning.[23]
Dye
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 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.
It can also be used to stain lymph nodes.
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.[24] This same side effect makes methylene blue difficult to test in traditional placebo-controlled clinical studies.[25]
Ifosfamide neurotoxicity
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[26] 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 50–60 mg up to six doses a day have resulted in improvement of symptoms within 10 minutes to several days.[27] Alternatively, it has been suggested that intravenous methylene blue 50 mg every six hours for prophylaxis during ifosfamide treatment in patients with history of ifosfamide neuropsychiatric toxicity.[28] Prophylactic administration of 50 mg of methylene blue the day before initiation of ifosfamide, and 50 mg three times daily during ifosfamide chemotherapy has been recommended to lower the occurrence of ifosfamide neurotoxicity.[29]
Clinical trials
TauRx Therapeutics has reported that methylene blue (methylthioninium chloride), under the tradename rember, may provide a way of halting or slowing the progression of Alzheimer's dementia.[30] However, the formulation used was different from that commonly available as a medicine and caution has been expressed about use of methylene blue as a treatment for Alzheimer's.[31] TauRx Therapeutics has suggested that the mechanism by which methylene blue might delay or reverse neurodegeneration in Alzheimer's disease is as an inhibitor of Tau protein aggregation. While methylene blue arguably has an effect on Tau aggregation, it also has an effect on mitochondrial function which is likely to play an important role. In vitro studies suggest that methylene blue might be an effective remedy for both Alzheimer's and Parkinson's disease by enhancing key mitochondrial biochemical pathways. It can disinhibit and increase complex IV, whose inhibition correlates with Alzheimer's disease.
Methylene blue might also delay senescence as one study has shown that it extended the lifespan of IMR90 fibroblasts by more than 20 population doublings.[32]
These findings are highly controversial, and a clear dosage response curve has not been found.
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. 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".[33]
As a prank
It is, or was at one time, a common prank among college students in biomedical fields to spike someone's drink with methylene blue, thus creating amusement at the victim's expense when he reacts with alarm to his urine turning blue. With concern over date rape drugs, spiking someone's drink is considered far more serious than it used to be, and the prank has somewhat gone out of fashion.
This prank has been used in television shows; for example:
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—who had been a high-ranked professional bowler in civilian life—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. In an episode of "ER" from the 5th season they use it to play an April Fools' Day prank on the desk clerk Jerry.[34]
Adverse reactions
| 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 • Bladder irritation |
• Anemia |
Causes hemolytic anemia in carriers of the G6PD (favism) enzymatic deficiency.
See also
- Gentian violet
- Methyl violet
- Dichlorophenolindophenol
- Fluorescein
- Prussian blue
- Egyptian Blue
- Han Purple
- Potassium ferrocyanide
- Potassium ferricyanide
- Phenothiazine structure
- Rember, investigational drug for Alzheimer's disease containing methylene blue
External links
References
Cite error: Invalid <references> tag;
parameter "group" is allowed only.
<references />, or <references group="..." />da:Methylenblåt de:Methylenblau es:Azul de metileno fa:متیلن بلو fr:Bleu de méthylène is:Metýlenblátt it:Blu di metilene nl:Methyleenblauw ja:メチレンブルー pl:Błękit metylenowy pt:Azul de metileno ru:Метиленовый синий fi:Metyleenisininen sv:Metylenblått uk:Метиленовий синій
zh:亞甲藍- ↑ http://www.methylene-blue.com/substance.php
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Spectroquant 114779 Sulfide Test. Method: photometric 0.020 - 1.50 mg/l S2-
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Healy, David (2002). The Creation of Psychopharmacology. Harvard University Press. ISBN 0674006194.
- ↑ Schirmer H, Coulibaly B, Stich A; et al. (2003). "Methylene blue as an antimalarial agent—past and future". Redox Rep. 8 (5): 272–276. doi:10.1179/135100003225002899. PMID 14962363.
- ↑ 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. PMC 1617109 Freely accessible. PMID 17026773.
- ↑ NQO1-activated phenothiazinium redox cyclers for the targeted bioreductive induction of cancer cell apoptosis. Wondrak GT. Free Radic Biol Med. 2007 Jul 15;43(2):178-90
- ↑ http://cancerres.aacrjournals.org/cgi/content/full/63/4/776
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ 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 Microbiol. 9: 27. doi:10.1186/1471-2180-9-27. PMC 2642833 Freely accessible. PMID 19193212.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Wagner SJ, Skripchenko A, Robinette D, Mallory DA, Hirayama J, Cincotta L, Foley J (2000). "The use of dimethylmethylene blue for virus photoinactivation of red cell suspensions". Dev Biol (Basel). 102: 125–9. PMID 10794099.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ 23.0 23.1 Matilda Moldenhauer Brooks (1936). "Methylene Blue as an Antidote for Cyanide and Carbon Monoxide Poisoning". The Scientific Monthly. 43 (6): 585–586.
- ↑ Novella Steve. "The Ethics of Deception in Medicine". Science Based Medicine. Retrieved 2008-01-24.
- ↑ "Methylene blue for cognitive dysfunction in bipolar disorder". United States National Library of Medicine. September 20, 2005. Retrieved 2009-02-15.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Patel PN (2006). "Methylene blue for management of ifosfamide induced encephalopathy". Ann Pharmacother. 40 (2): 266–303. doi:10.1345/aph.1G114. PMID 16391008.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Aeschlimann T; Cerny, T; Küpfer, A (1996). "Inhibition of (mono)amine oxidase activity and prevention of ifosfamide encephalopathy by methylene blue". Drug Metab Dispos. 24 (12): 1336–1339. PMID 8971139.
- ↑ "Alzheimer's drug 'halts' decline". BBC News. 2008-07-30. Retrieved 2008-07-30.
- ↑ "Slowing disease's mental ravages". Chicago Tribune. 2008-07-30.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ [1] Aquarium Chemical Treatments
- ↑ "Medical use with side effects indicating blue urine". Medicinenet.com.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- Pages with script errors
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- Chemboxes which contain changes to watched fields
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- Antidotes
- Histology
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