text:
Methylene blue
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Not to be confused with methyl blue, new methylene blue, or methyl violet.
Methylene blue
Clinical data
Trade names
Urelene blue, Provayblue, Proveblue, other[2][3]
Synonyms
CI 52015
AHFS/Drugs.com
Monograph
Pregnancy
category
AU: D
US: X (Contraindicated) [1]
Routes of
administration
by mouth, IV
ATC code
none
Legal status
Legal status
US: Medication Rx-only[1]
Identifiers
IUPAC name[show]
3,7-bis(Dimethylamino)-phenothiazin-5-ium chloride
CAS Number
61-73-4 Y
PubChem CID
6099
ChemSpider
5874 Y
KEGG
D10537
ChEBI
CHEBI:6872 Y
ChEMBL
CHEMBL405110 Y
ECHA InfoCard
100.000.469
Chemical and physical data
Formula
C16H18ClN3S
Molar mass
319.85 g/mol
3D model (JSmol)
Interactive image
SMILES[show]
CN(C)c1ccc2c(c1)sc-3cc(=[N+](C)C)ccc3n2.[Cl-]
InChI[show]
InChI=1S/C16H18N3S.ClH/c1-18(2)11-5-7-13-15(9-11)20-16-10-12(19(3)4)6-8-14(16)17-13;/h5-10H,1-4H3;1H/q+1;/p-1 Y
Key:CXKWCBBOMKCUKX-UHFFFAOYSA-M Y
(verify)
Methylene blue, also known as methylthioninium chloride, is a medication and dye.[1] As a medication, it is mainly used to treat methemoglobinemia.[1][3] Specifically, it is used to treat methemoglobin levels that are greater than 30% or in which there are symptoms despite oxygen therapy.[3] It has previously been used for cyanide poisoning and urinary tract infections, but this use is no longer recommended.[1] It is typically given by injection into a vein.[1]
Common side effects include headache, vomiting, confusion, shortness of breath, and high blood pressure.[1] Other side effects include serotonin syndrome, red blood cell breakdown, and allergic reactions.[1] Use often turns the urine, sweat, and stool blue to green in color.[3] While use during pregnancy may harm the baby, not using in methemoglobinemia is likely more dangerous.[1][3] Methylene blue is a thiazine dye.[1] It works by converting the ferric iron in hemoglobin to ferrous iron.[3]
Methylene blue was first prepared in 1876 by Heinrich Caro.[4] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[5] In the United States, a 50 mg vial costs about 191.40 USD.[6] In the United Kingdom, a 50 mg vial costs the NHS about £39.38.[3]
Contents
[hide]
1 Medical uses
1.1 Methemoglobinemia
1.2 Combined with light
1.3 Urinary tract infection
1.4 Cyanide poisoning
1.5 Dye or stain
1.6 Placebo
1.7 Ifosfamide toxicity
1.8 Vasoplegic syndrome
2 Side effects
3 Chemistry
3.1 Preparation
3.2 Light absorption properties
4 Other uses
4.1 Redox indicator
4.2 Peroxide generator
4.3 Sulfide analysis
4.4 Water testing
4.5 Methylene blue value of fine aggregate
4.6 Biological staining
4.7 Aquaculture
5 History
6 Names
7 Research
7.1 Malaria
7.2 Alzheimer's
7.3 Bipolar disorder
7.4 Viruses
8 See also
9 References
10 External links
Medical uses[edit]
Methemoglobinemia[edit]
Methylene blue is employed as a medication for the treatment of methemoglobinemia. This can arise from ingestion of certain pharmaceuticals, toxins, or broad beans.[7] Normally, through the NADH or NADPH dependent methemoglobin reductase enzymes, methemoglobin is reduced back to hemoglobin. When large amounts of methemoglobin occur secondary to toxins, methemoglobin reductases are overwhelmed. Methylene blue, when injected intravenously as an antidote, is itself first reduced to leucomethylene blue, which then reduces the heme group from methemoglobin to hemoglobin. Methylene blue can reduce the half life of methemoglobin from hours to minutes.[8] At high doses, however, methylene blue actually induces methemoglobinemia, reversing this pathway.[8]
Combined with light[edit]
Methylene blue combined with light has been used to treat resistant plaque psoriasis.[9]
Urinary tract infection[edit]
Methylene blue is a component of a frequently prescribed urinary analgesic/anti-infective/anti-spasmodic known as "Prosed DS", a combination of drugs which also contains phenyl salicylate, benzoic acid, hyoscyamine sulfate, and methenamine (aka hexamethylenetetramine and not to be confused with 'methanamine').[10]
Cyanide poisoning[edit]
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,[11] although first demonstrated by Bo Sahlin of Lund University, in 1926.[11][12]
Dye or stain[edit]
Human cheek cells stained with methylene blue
Methylene blue is used in endoscopic polypectomy as an adjunct to saline or epinephrine, and is used for injection into the submucosa around the polyp to be removed. This allows the submucosal tissue plane to be identified after the polyp is removed, which is useful in determining if more tissue needs to be removed, or if there has been a high risk for perforation. Methylene blue is also used as a dye in chromoendoscopy, and is sprayed onto the mucosa of the gastrointestinal tract in order to identify dysplasia, or pre-cancerous lesions. Intravenously injected methylene blue is readily released into the urine and thus can be used to test the urinary tract for leaks or fistulas.
In surgeries such as sentinel lymph node dissections, methylene blue can be used to visually trace the lymphatic drainage of tested tissues. Similarly, methylene blue is added to bone cement in orthopedic operations to provide easy discrimination between native bone and cement. Additionally, methylene blue accelerates the hardening of bone cement, increasing the speed at which bone cement can be effectively applied. Methylene blue is used as an aid to visualisation/orientation in a number of medical devices, including a Surgical sealant film, TissuePatch.
When methylene blue is "polychromed" (oxidized in solution or "ripened" by fungal metabolism,[13] as originally noted in the thesis of Dr. D. L. Romanowsky in the 1890s), it gets serially demethylated and forms all the tri-, di-, mono- and non-methyl intermediates, which are Azure B, Azure A, Azure C, and thionine, respectively.[14] This is the basis of the basophilic part of the spectrum of Romanowski-Giemsa effect. If only synthetic Azure B and Eosin Y is used, it may serve as a standardized Giemsa stain; but, without methylene blue, the normal neutrophilic granules tend to overstain and look like toxic granules. On the other hand, if methylene blue is used it might help to give the normal look of neutrophil granules and may also enhance the staining of nucleoli and polychromatophilic RBCs (reticulocytes).[15]
A traditional application of methylene blue is the intravital or supravital staining of nerve fibers, an effect first described by Paul Ehrlich in 1887.[16] A dilute solution of the dye is either injected into tissue or applied to small freshly removed pieces. The selective blue coloration develops with exposure to air (oxygen) and can be fixed by immersion of the stained specimen in an aqueous solution of ammonium molybdate. Vital methylene blue was formerly much used for examining the innervation of muscle, skin and internal organs.[17][18][19] The mechanism of selective dye uptake is incompletely understood; vital staining of nerve fibers in skin is prevented by ouabain, a drug that inhibits the Na/K-ATPase of cell membranes.[20]
Placebo[edit]
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.[21] This same side effect makes methylene blue difficult to test in traditional placebo-controlled clinical studies.[22]
Ifosfamide toxicity[edit]
Another use of methylene blue is to treat ifosfamide neurotoxicity. Methylene blue was first reported for treatment and prophylaxis of ifosfamide neuropsychiatric toxicity in 1994. A toxic metabolite of ifosfamide, chloroacetaldehyde (CAA), disrupts the mitochondrial respiratory chain, leading to an accumulation of nicotinamide adenine dinucleotide hydrogen (NADH). Methylene blue acts as an alternative electron acceptor, and reverses the NADH inhibition of hepatic gluconeogenesis while also inhibiting the transformation of chloroethylamine into chloroacetaldehyde, and inhibits multiple amine oxidase activities, preventing the formation of CAA.[23] The dosing of methylene blue for treatment of ifosfamide neurotoxicity varies, depending upon its use simultaneously as an adjuvant in ifosfamide infusion, versus its use to reverse psychiatric symptoms that manifest after completion of an ifosfamide infusion. Reports suggest that methylene blue up to six doses a day have resulted in improvement of symptoms within 10 minutes to several days.[24] Alternatively, it has been suggested that intravenous methylene blue every six hours for prophylaxis during ifosfamide treatment in patients with history of ifosfamide neuropsychiatric toxicity.[25] Prophylactic administration of methylene blue the day before initiation of ifosfamide, and three times daily during ifosfamide chemotherapy has been recommended to lower the occurrence of ifosfamide neurotoxicity.[26]
Vasoplegic syndrome[edit]
Some literature has reported the use of methylene blue as an adjunct in the management of people experiencing vasoplegic syndrome after cardiac surgery.[27][28][29]
Side effects[edit]
Cardiovascular
Central Nervous System
Dermatologic
Gastrointestinal
Genito-urinary
Hematologic
• Hypertension
• Precordial pain • Dizziness
• Mental confusion
• Headache
• Fever • Staining of skin
• Injection site necrosis (SC) • Fecal discoloration
• Nausea
• Vomiting
• Abdominal pain • Discoloration of urine (doses over 80 µg)
• Bladder irritation • Anemia
[30][31]
Methylene blue is a monoamine oxidase inhibitor (MAOI),[32] 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).[33]
It causes hemolytic anemia in carriers of the G6PD (favism) enzymatic deficiency.
Chemistry[edit]
Methylene blue is a formal derivative of phenothiazine. It is a dark green powder that yields a blue solution in water. The hydrated form has 3 molecules of water per unit of methylene blue. Methylene blue has a pH of 3 in water(10g/l) at 25 °C (77 °F).
Preparation[edit]
This compound is prepared by oxidation of dimethyl-4-phenylenediamine in the presence of sodium thiosulfate.[34]
Light absorption properties[edit]
Absorption spectrum of methylene blue, in terms of the molar extinction coefficient (base 10 logarithm). In this dataset a peak absorbance of 1.7 (i.e. 98% of transmitted light absorbed) was observed with 665 nm light passing through 1 cm of 10 micromolar methylene blue solution.
The maximum absorption of light is near 670 nm. The specifics of absorption depend on a number of factors, including protonation, adsorption to other materials, and metachromasy - the formation of dimers and higher-order aggregates depending on concentration and other interactions:[35]
Species
Absorption peak
Extinction coefficient (dm3/mole·cm)
MB+ (solution) 664 95000
MBH2+ (solution) 741 76000
(MB+)2 (solution) 605 132000
(MB+)3 (solution) 580 110000
MB+ (adsorbed on clay) 673 116000
MBH2+ (adsorbed on clay) 763 86000
(MB+)2 (adsorbed on clay) 596 80000
(MB+)3 (adsorbed on clay) 570 114000
Other uses[edit]
A volumetric flask of a methylene blue solution
Redox indicator[edit]
Methylene blue is widely used as a redox indicator in analytical chemistry. Solutions of this substance are blue when in an oxidizing environment, but will turn colorless if exposed to a reducing agent. The redox properties can be seen in a classical demonstration of chemical kinetics in general chemistry, the "blue bottle" experiment. Typically, a solution is made of glucose (dextrose), methylene blue, and sodium hydroxide. Upon shaking the bottle, oxygen oxidizes methylene blue, and the solution turns blue. The dextrose will gradually reduce the methylene blue to its colorless, reduced form. Hence, when the dissolved dextrose is entirely consumed, the solution will turn blue again. The redox midpoint potential E0' is +0.011 mV.[36]
Peroxide generator[edit]
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[edit]
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[37] facilitate routine analyses. The methylene blue sulfide test is a convenient method often used in soil microbiology to quickly detect in water the metabolic activity of sulfate reducing bacteria (SRB). It should be observed that in this test, methylene blue is a product of reaction and not a reagent.
The addition of a strong reducing agent, such as ascorbic acid, to a sulfide-containing solution is sometimes used to prevent sulfide oxidation from atmospheric oxygen. Although it is certainly a sound precaution for the determination of sulfide with an ion selective electrode, it might however hamper the development of the blue color if the freshly formed methylene blue is also reduced, as described here above in the paragraph on redox indicator.
Water testing[edit]
Further information: MBAS assay
A color reaction in an acidified, aqueous methylene blue solution containing chloroform can detect anionic surfactants in a water sample. Such a test is known as an MBAS assay (methylene blue active substances assay).
The MBAS assay cannot distinguish between specific surfactants, however. Some examples of anionic surfactants are carboxylates, phosphates, sulfates, and sulfonates.
Methylene blue value of fine aggregate[edit]
Methylene blue value reflects the amount of clay minerals in aggregate samples.[38] Methylene blue solution is successively added to fine aggregate which is being agitating in water. The presence of free dye solution can be checked with stain test on a filter paper.[39]
Biological staining[edit]
In biology methylene blue is used as a dye for a number of different staining procedures, such as Wright's stain and Jenner's stain. Since it is a temporary staining technique, methylene blue can also be used to examine RNA or DNA under the microscope or in a gel: as an example, a solution of methylene blue can be used to stain RNA on hybridization membranes in northern blotting to verify the amount of nucleic acid present. While methylene blue is not as sensitive as ethidium bromide, it is less toxic and it does not intercalate in nucleic acid chains, thus avoiding interference with nucleic acid retention on hybridization membranes or with the hybridization process itself.
It can also be used as an indicator to determine whether eukaryotic cells such as yeast are alive or dead. The methylene blue is reduced in viable cells, leaving them unstained. However dead cells are unable to reduce the oxidized methylene blue and the cells are stained blue. Methylene blue can interfere with the respiration of the yeast as it picks up hydrogen ions made during the process.
Aquaculture[edit]
Methylene blue is used in aquaculture and by tropical fish hobbyists as a treatment for fungal infections. It can also be effective in treating fish infected with ich although a combination of malachite green and formaldehyde is far more effective against the parasitic protozoa Ichthyophthirius multifiliis. It is usually used to protect newly laid fish eggs from being infected by fungus or bacteria. This is useful when the hobbyist wants to artificially hatch the fish eggs. Methylene Blue is also very effective when used as part of a "medicated fish bath" for treatment of ammonia, nitrite, and cyanide poisoning as well as for topical and internal treatment of injured or sick fish as a "first response".[40]
History[edit]
Methylene blue has been described as "the first fully synthetic drug used in medicine." Methylene blue was first prepared in 1876 by German chemist Heinrich Caro.[41]
Its use in the treatment of malaria was pioneered by Paul Guttmann and Paul Ehrlich in 1891. During this period before the first World War, researchers like Ehrlich believed that drugs and dyes worked in the same way, by preferentially staining pathogens and possibly harming them. Methylene blue continued to be used in the second World War, where it was not well liked by soldiers, who observed, "Even at the loo, we see, we pee, navy blue." Antimalarial use of the drug has recently been revived.[42] It was discovered to be an antidote to carbon monoxide poisoning and cyanide poisoning in 1933 by Matilda Brooks.[43]
The blue urine was used to monitor psychiatric patients' compliance with medication regimes. This led to interest - from the 1890s to the present day - in the drug's antidepressant and other psychotropic effects. It became the lead compound in research leading to the discovery of chlorpromazine.[44]
Names[edit]
The International Nonproprietary Name (INN) of methylene blue is methylthioninium chloride.[45][46]
Research[edit]
Malaria[edit]
Methylene blue was identified by Paul Ehrlich about 1891 as a possible treatment for malaria.[47] It disappeared as an anti-malarial during the Pacific War in the tropics, since American and Allied soldiers disliked its two prominent, but reversible side effects: turning the urine blue or green, and the sclera (the whites of the eyes) blue. Interest in its use as an anti-malarial has recently been revived,[44] especially due to its low price. Several clinical trials are in progress, trying to find a suitable drug combination. According to studies on children in Africa, it appears to have efficacy against malaria, but the attempts to combine methylene blue with chloroquine were disappointing.[48]
Alzheimer's[edit]
A Phase 3 clinical trial of LMTM (TauRx0237 or LMT-X), a derivative of methylene blue, failed to show any benefit against cognitive or functional decline in people with mild to moderate Alzheimer’s disease. Disease progression for both the drug and the placebo were practically identical.[49][50]
Bipolar disorder[edit]
Methylene blue has been studied as an adjunctive medication in the treatment of bipolar disorder.[51]
Viruses[edit]
It has been studied in AIDS-related Kaposi's sarcoma,[52] West Nile virus,[53] and to inactivate staphylococcus aureus,[54] and HIV-1.[55] Phenothiazine dyes and light have been known to have virucidal properties for over 70 years.[56]
See also[edit]
New methylene blue
Phenothiazine structure
Rember, investigational drug for Alzheimer's disease containing methylene blue
Romanowsky stain
Methyl violet
Gentian violet
Fluorescein
Prussian blue
Egyptian Blue
Methyl blue
Han Purple
Potassium ferrocyanide
Potassium ferricyanide
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Jump up ^ Tardivo J.P.; Del Giglio A.; Paschoal L.H.; Baptista M.S. (August 2006). "New photodynamic therapy protocol to treat AIDS-related Kaposi's sarcoma". Photomedical Laser Surg. 24 (4): 528–31. doi:10.1089/pho.2006.24.528. PMID 16942436.
Jump up ^ Papin J.F.; Floyd R.A.; Dittmer D.P. (November 2005). "Methylene blue photoinactivation abolishes West Nile virus infectivity in vivo". Antiviral Res. 68 (2): 84–7. doi:10.1016/j.antiviral.2005.07.001. PMID 16118025.
Jump up ^ Zolfaghari P.S.; Packer S.; Singer M.; Nair S.P.; 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  . PMID 19193212.
Jump up ^ Floyd R.A.; Schneider J.E.; Dittmer D.P. (March 2004). "Methylene blue photoinactivation of RNA viruses". Antiviral Res. 61 (3): 141–51. doi:10.1016/j.antiviral.2003.11.004. PMID 15168794.
Jump up ^ Wagner S.J.; Skripchenko A.; Robinette D.; Mallory D.A.; 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.
External links[edit]
NIH - Methylene blue test
Methylene blue at stainsfile
[show]
v
t
e
Antidotes (V03AB)
Nervous
system
Nerve agent /
Organophosphate
poisoning
Atropine#
Biperiden
Diazepam#
Oximes
Obidoxime
Pralidoxime
see also: Cholinesterase
Barbiturate
overdose
Bemegride
Ethamivan
Benzodiazepine
overdose
Cyprodenate
Flumazenil
GHB overdose
Physostigmine
SCH-50911
Opioid overdose
Diprenorphine
Doxapram
Nalmefene
Nalorphine
Naloxone#
Naltrexone
Reversal of
neuromuscular blockade
Sugammadex
Circulatory
system
Beta blocker
Glucagon
Digoxin toxicity
Digoxin Immune Fab
Heparin
Protamine#
Other
Arsenic poisoning
Dimercaprol#
Succimer
Cyanide poisoning
4-Dimethylaminophenol
Hydroxocobalamin
nitrite
Amyl nitrite
Sodium nitrite#
Sodium thiosulfate#
Hydrofluoric acid
Calcium gluconate#
Methanol /
Ethylene glycol
poisoning
Primary alcohols: Ethanol
Fomepizole
Paracetamol toxicity
(Acetaminophen)
Acetylcysteine#
Glutathione
Methionine#
Toxic metals (cadmium
lead
mercury
thallium)
Dimercaprol#
Edetates
Prussian blue#
Other
iodine-131
Potassium iodide
Methylthioninium chloride#
oxidizing agent
Potassium permanganate
Prednisolone/promethazine
Emetic
Copper sulfate
Ipecacuanha
Syrup of ipecac
#WHO-EM
‡Withdrawn from market
Clinical trials:
†Phase III
§Never to phase III
[show]
v
t
e
Microbial and histological stains
Iron/hemosiderin
Prussian blue
Lipids
Sudan stain
Sudan II
Sudan III
Sudan IV
Oil Red O
Sudan Black B
Carbohydrates
Periodic acid–Schiff stain
Amyloid
Congo red
Bacteria
Gram stain
Methyl violet/Gentian violet
Safranin
Ziehl–Neelsen stain/acid-fast
Carbol fuchsin/Fuchsine
Methylene blue
Auramine-rhodamine stain
Auramine O
Rhodamine B
Connective tissue
trichrome stain: Masson's trichrome stain/Lillie's trichrome
Light Green SF yellowish
Biebrich scarlet
Phosphomolybdic acid
Fast Green FCF
Van Gieson's stain
Other
H&E stain
Haematoxylin
Eosin Y
Silver stain
Grocott's methenamine silver stain
Warthin–Starry stain
Methyl blue
Wright's stain
Giemsa stain
Gömöri trichrome stain
Neutral red
Janus Green B
Alcian blue stain
Movat's stain
Jaswant Singh–Bhattacharji (JSB) stain
Tissue stainability
Acidophilic
Basophilic
Chromophobic
[show]
Glutamate receptor modulators
[show]
v
t
e
Ionotropic glutamate receptor modulators
AMPAR
Agonists: Main site agonists: 5-Fluorowillardiine
Acromelic acid (acromelate)
AMPA
BOAA
Domoic acid
Glutamate
Ibotenic acid
Proline
Quisqualic acid
Willardiine; Positive allosteric modulators: Aniracetam
Cyclothiazide
CX-516
CX-546
CX-614
Farampator (CX-691, ORG-24448)
CX-717
CX-1739
CX-1942
Diazoxide
Hydrochlorothiazide (HCTZ)
IDRA-21
LY-392098
LY-395153
LY-404187
LY-451646
LY-503430
Mibampator (LY-451395)
Nooglutyl
ORG-26576
Oxiracetam
PEPA
PF-04958242
Piracetam
Pramiracetam
S-18986
Tulrampator (S-47445, CX-1632)
Antagonists: ACEA-1011
ATPO
Becampanel
Caroverine
CNQX
Dasolampanel
DNQX
Fanapanel (MPQX)
GAMS
Kaitocephalin
Kynurenic acid
Kynurenine
Licostinel (ACEA-1021)
NBQX
PNQX
Selurampanel
Tezampanel
Theanine
Topiramate
YM90K
Zonampanel; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental)
Cyclopropane
Enflurane
Ethanol (alcohol)
Evans blue
GYKI-52466
GYKI-53655
Halothane
Irampanel
Isoflurane
Perampanel
Pregnenolone sulfate
Sevoflurane
Talampanel; Unknown/unsorted antagonists: Minocycline
KAR
Agonists: Main site agonists: 5-Bromowillardiine
5-Iodowillardiine
Acromelic acid (acromelate)
AMPA
ATPA
Domoic acid
Glutamate
Ibotenic acid
Kainic acid
LY-339434
Proline
Quisqualic acid
SYM-2081; Positive allosteric modulators: Cyclothiazide
Diazoxide
Enflurane
Halothane
Isoflurane
Antagonists: ACEA-1011
CNQX
Dasolampanel
DNQX
GAMS
Kaitocephalin
Kynurenic acid
Licostinel (ACEA-1021)
LY-382884
NBQX
NS102
Selurampanel
Tezampanel
Theanine
Topiramate
UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental)
Enflurane
Ethanol (alcohol)
Evans blue
NS-3763
Pregnenolone sulfate
NMDAR
Agonists: Main site agonists: AMAA
Aspartate
Glutamate
Homocysteic acid (L-HCA)
Homoquinolinic acid
Ibotenic acid
NMDA
Proline
Quinolinic acid
Tetrazolylglycine
Theanine; Glycine site agonists: β-Fluoro-D-alanine
ACBD
ACC (ACPC)
ACPD
AK-51
Apimostinel (NRX-1074)
B6B21
CCG
D-Alanine
D-Cycloserine
D-Serine
DHPG
Dimethylglycine
Glycine
HA-966
L-687414
L-Alanine
L-Serine
Milacemide
Neboglamine (nebostinel)
Rapastinel (GLYX-13)
Sarcosine; Polyamine site agonists: Neomycin
Spermidine
Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol
DHEA (prasterone)
DHEA sulfate (prasterone sulfate)
Epipregnanolone sulfate
Pregnenolone sulfate
SAGE-201
SAGE-301
SAGE-718
Antagonists: Competitive antagonists: AP5 (APV)
AP7
CGP-37849
CGP-39551
CGP-39653
CGP-40116
CGS-19755
CPP
Kaitocephalin
LY-233053
LY-235959
LY-274614
MDL-100453
Midafotel (d-CPPene)
NPC-12626
NPC-17742
PBPD
PEAQX
Perzinfotel
PPDA
SDZ-220581
Selfotel; Glycine site antagonists: 4-Cl-KYN (AV-101)
5,7-DCKA
7-CKA
ACC
ACEA-1011
ACEA-1328
Apimostinel (NRX-1074)
AV-101
Carisoprodol
CGP-39653
CNQX
D-Cycloserine
DNQX
Felbamate
Gavestinel
GV-196771
Harkoseride
Kynurenic acid
Kynurenine
L-689560
L-701324
Licostinel (ACEA-1021)
LU-73068
MDL-105519
Meprobamate
MRZ 2/576
PNQX
Rapastinel (GLYX-13)
ZD-9379; Polyamine site antagonists: Arcaine
Co 101676
Diaminopropane
Diethylenetriamine
Huperzine A
Putrescine; Uncompetitive pore blockers (mostly dizocilpine site): 2-MDP
3-HO-PCP
3-MeO-PCE
3-MeO-PCMo
3-MeO-PCP
4-MeO-PCP
8A-PDHQ
18-MC
α-Endopsychosin
Alaproclate
Alazocine (SKF-10047)
Amantadine
Aptiganel
Argiotoxin-636
Arketamine
ARL-12495
ARL-15896-AR
ARL-16247
Budipine
Coronaridine
Delucemine (NPS-1506)
Dexoxadrol
Dextrallorphan
Dextromethadone
Dextromethorphan
Dextrorphan
Dieticyclidine
Diphenidine
Dizocilpine
Ephenidine
Esketamine
Etoxadrol
Eticyclidine
Fluorolintane
Gacyclidine
Ibogaine
Ibogamine
Indantadol
Ketamine
Ketobemidone
Lanicemine
Levomethadone
Levomethorphan
Levomilnacipran
Levorphanol
Loperamide
Memantine
Methadone
Methorphan
Methoxetamine
Methoxphenidine
Milnacipran
Morphanol
NEFA
Neramexane
Nitromemantine
Noribogaine
Norketamine
Orphenadrine
PCPr
PD-137889
Pethidine (meperidine)
Phencyclamine
Phencyclidine
Propoxyphene
Remacemide
Rhynchophylline
Rimantadine
Rolicyclidine
Sabeluzole
Tabernanthine
Tenocyclidine
Tiletamine
Tramadol; Ifenprodil (NR2B) site antagonists:
Besonprodil
Buphenine (nylidrin)
CO-101244 (PD-174494)
Eliprodil
Haloperidol
Isoxsuprine
Radiprodil (RGH-896)
Rislenemdaz (CERC-301, MK-0657)
Ro 8-4304
Ro 25-6981
Safaprodil
Traxoprodil (CP-101606); NR2A-selective antagonists: MPX-004
MPX-007
TCN-201
TCN-213; Cations: Hydrogen
Magnesium
Zinc; Alcohols/volatile anesthetics/related: Benzene
Butane
Chloroform
Cyclopropane
Desflurane
Diethyl ether
Enflurane
Ethanol (alcohol)
Halothane
Hexanol
Isoflurane
Methoxyflurane
Nitrous oxide
Octanol
Sevoflurane
Toluene
Trichloroethane
Trichloroethanol
Trichloroethylene
Urethane
Xenon
Xylene; Unknown/unsorted antagonists: ARR-15896
Bumetanide
Caroverine
Conantokin
D-αAA
Dexanabinol
Flufenamic acid
Flupirtine
FPL-12495
FR-115427
Furosemide
Hodgkinsine
Ipenoxazone (MLV-6976)
MDL-27266
Metaphit
Minocycline
MPEP
Niflumic acid
Pentamidine
Pentamidine isethionate
Piretanide
Psychotridine
Transcrocetin (saffron)
See also: Receptor/signaling modulators
Metabotropic glutamate receptor modulators
Glutamate metabolism/transport modulators
[show]
v
t
e
Metabotropic glutamate receptor modulators
Group I
mGluR1
Agonists: ACPD
DHPG
Glutamate
Ibotenic acid
Quisqualic acid
Ro01-6128
Ro67-4853
Ro67-7476
VU-71
Theanine
Antagonists: BAY 36-7620
CPCCOEt
Cyclothiazide
LY-367,385
LY-456,236
MCPG
NPS-2390
mGluR5
Agonists: ACPD
ADX-47273
CDPPB
CHPG
DFB
DHPG
Glutamate
Ibotenic acid
Quisqualic acid
VU-1545
Antagonists: CTEP
DMeOB
LY-344,545
Mavoglurant
MCPG
NPS-2390
Remeglurant
SIB-1757
SIB-1893; Negative allosteric modulators: Basimglurant
Dipraglurant
Fenobam
GRN-529
MPEP
MTEP
Raseglurant
Group II
mGluR2
Agonists: BINA
CBiPES
DCG-IV
Eglumegad
Glutamate
Ibotenic acid
LY-379,268
LY-404,039 (pomaglumetad)
LY-487,379
LY-566,332
MGS-0028
Pomaglumetad methionil (LY-2140023)
Talaglumetad; Positive allosteric modulators: JNJ-40411813 (ADX-71149)
Antagonists: APICA
CECXG
EGLU
HYDIA
LY-307,452
LY-341,495
MCPG
MGS-0039
PCCG-4; Negative allosteric modulators: Decoglurant
RO4491533
mGluR3
Agonists: CBiPES
DCG-IV
Eglumegad
Glutamate
Ibotenic acid
LY-379,268
LY-404,039 (pomaglumetad)
LY-487,379
MGS-0028
Pomaglumetad methionil (LY-2140023)
Talaglumetad
Antagonists: APICA
CECXG
EGLU
HYDIA
LY-307,452
LY-341,495
MCPG
MGS-0039; Negative allosteric modulators: Decoglurant
RO4491533
Group III
mGluR4
Agonists: Glutamate
L-AP4
PHCCC
VU-001,171
VU-0155,041; Positive allosteric modulators: Foliglurax
MPEP
Antagonists: CPPG
MAP4
MPPG
MSOP
MTPG
UBP-1112
mGluR6
Agonists: Glutamate
L-AP4
Antagonists: CPPG
MAP4
MPPG
MSOP
MTPG
UBP-1112
mGluR7
Agonists: AMN082
Glutamate
L-AP4
Antagonists: CPPG
MAP4
MMPIP
MPPG
MSOP
MTPG
UBP-1112
mGluR8
Agonists: DCPG
Glutamate
L-AP4
Antagonists: CPPG
MAP4
MPPG
MSOP
MTPG
UBP-1112
See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Glutamate metabolism/transport modulators
[show]
v
t
e
Monoamine metabolism modulators
Non-specific
AAAD
Substrates→Products: L-DOPA (levodopa)→Dopamine
5-HTP→Serotonin
L-Histidine→Histamine
Phenylalanine→Phenethylamine
L-Tyrosine→Tyramine
Tryptophan→Tryptamine
Inhibitors: Benserazide
Carbidopa
DFMD
Genistein
Methyldopa
MAO
Substrates→Products (with ALDH/ALR): Epinephrine (adrenaline)→DHMA
Metanephrine→MHPG/VMA
Norepinephrine (noradrenaline)→DHMA
Normetanephrine→MHPG/VMA
Dopamine→DOPAC
3-Methoxytyramine→HVA
Serotonin→5-HIAA
Inhibitors: Non-selective: Benmoxin
Caroxazone
Echinopsidine
Furazolidone
Guineesine
Hydralazine
Indantadol
Iproclozide
Iproniazid
Isocarboxazid
Isoniazid
Linezolid
Mebanazine
Metfendrazine
Nialamide
Octamoxin
Paraxazone
Phenelzine
Pheniprazine
Phenoxypropazine
Pivhydrazine
Procarbazine
Safrazine
Tranylcypromine
Inhibitors: MAO-A-selective: Amiflamine
Bazinaprine
Befloxatone
Brofaromine
Cimoxatone
Clorgiline
CX157 (Tyrima)
Eprobemide
Esuprone
Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine)
Methylene blue
Metralindole
Minaprine
Moclobemide
Pirlindole
Sercloremine
Tetrindole
Toloxatone
Inhibitors: MAO-B selective: Adarigiline
Almoxatone
D-Deprenyl
Ethanol
Ladostigil
Lazabemide
Milacemide
Mofegiline
Nicotine
Pargyline‡
Rasagiline
Safinamide
Selegiline (L-Deprenyl)
Sembragiline
Phenethylamines
(dopamine, epinephrine,
norepinephrine)
PAH
Substrates→Products: Phenylalanine→Tyrosine
Inhibitors: 3,4-Dihydroxystyrene
TH
Substrates→Products: Tyrosine→L-DOPA (levodopa)
Inhibitors: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Iodotyrosine
Aquayamycin
Bulbocapnine
Metirosine
Oudenone
DBH
Substrates→Products: Dopamine→Norepinephrine (Noradrenaline)
Inhibitors: Bupicomide
Disulfiram
Dopastin
Fusaric acid
Nepicastat
Phenopicolinic acid
Tropolone
PNMT
Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine (adrenaline)
Inhibitors: CGS-19281A
SKF-64139
SKF-7698
COMT
Substrates→Products: Dopamine→3-Methoxytyramine
DOPAC→Homovanillic acid
Norepinephrine→Normetanephrine
Epinephrine→Metanephrine
DOPEG→MOPEG
DOMA→VMA
2-Hydroxyestradiol→2-Methoxyestradiol
2-Hydroxyestrone→2-Methoxyestrone
4-Hydroxyestradiol→4-Methoxyestradiol
4-Hydroxyestrone→4-Methoxyestrone
Inhibitors: 2-Hydroxyestradiol
2-Hydroxyestrone
Entacapone
Nitecapone
Opicapone
Tolcapone
Tryptamines
(serotonin, melatonin)
TPH
Substrates→Products: Tryptophan→5-HTP
Inhibitors: AGN-2979
Fenclonine (PCPA)
Telotristat ethyl
AANAT
Substrates→Products: Serotonin→N-Acetylserotonin
ASMT
Substrates→Products: N-Acetylserotonin→Melatonin
Histamine
HDC
Substrates→Products: L-Histidine→Histamine
Inhibitors: Catechin
Meciadanol
Naringenin
Tritoqualine
HNMT
Substrates→Products: Histamine→N-Methylhistamine
Inhibitors: Amodiaquine
Diphenhydramine
Harmaline
Metoprine
Quinacrine
SKF-91,488
Tacrine
DAO
Substrates→Products: Histamine→Imidazole acetic acid
Inhibitors: Pimagedine (aminoguanidine)
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins
[show]
v
t
e
Tricyclics
Classes
Acridine
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Dibenzothiazepine
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Pyridazinobenzoxazine
Pyridinobenzodiazepine
Thioxanthene
Antidepressants
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7-OH-Amoxapine
Amezepine
Amineptine
Amitriptyline
Amitriptylinoxide
Amoxapine
Aptazapine
Azepindole
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Batelapine
Butriptyline
Cianopramine
Ciclazindol
Ciclopramine
Cidoxepin
Clomipramine
Cotriptyline
Cyanodothiepin
Demexiptiline
Depramine (balipramine)
Desipramine (desmethylimipramine)
Desmethylclomipramine
Desmethyltrimipramine
Dibenzepin
Dimetacrine
Dosulepin (dothiepin)
Doxepin
Enprazepine
Esmirtazapine
Fantridone
Fluotracen
Hepzidine
Homopipramol
Imipramine
Imipraminoxide
Intriptyline
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Litracen
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