Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H7N3O2 |
| Molecular Weight | 177.1601 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=CC=CC2=C1C(=O)NNC2=O
InChI
InChIKey=HWYHZTIRURJOHG-UHFFFAOYSA-N
InChI=1S/C8H7N3O2/c9-5-3-1-2-4-6(5)8(13)11-10-7(4)12/h1-3H,9H2,(H,10,12)(H,11,13)
| Molecular Formula | C8H7N3O2 |
| Molecular Weight | 177.1601 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Luminol (5-amino-2,3-dihydro-1,4-phthalazinedione) is a yellow-colored crystalline solid powder and soluble in most polar organic solvents, but insoluble in water. An alkaline solution of luminol oxidized by oxidizing agents exhibits chemiluminescence. Luminol was first synthesized by Schmitz in 1902, the chemiluminescence property of luminol was first discovered by Albrecht in 1928. Luminol is one of the most widely used chemiluminescent compounds because of its availability and low cost. Luminol-based methods are used in environmental monitoring as biosensors, in the pharmaceutical industry for cellular localization and as biological tracers, and in reporter gene-based assays and several other immunoassays.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Priming-phenomenon of neutrophils in patients with Flexner infection]. | 2001 |
|
| Menadione-catalyzed luminol chemiluminescent assay for the viability of Escherichia coli ATCC 25922. | 2001 |
|
| Generation of choline for acetylcholine synthesis by phospholipase D isoforms. | 2001 |
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| Insulin-induced peroxynitrite production in human platelet-rich plasma. | 2001 |
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| Flow-through chemiluminescence sensor using immobilized oxidases for the selective determination of L-glutamate in a flow-injection system. | 2001 Aug |
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| Capillary electrophoresis with chemiluminescent detection for luminol using potassium ferricyanide as a catalyst. | 2001 Aug |
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| Reactive oxygen species activity, mucosal lipoperoxidation and glutathione in Helicobacter pylori-infected gastric mucosa. | 2001 Dec |
|
| Chemiluminescence investigation of detection of rutin in medicine and human urine using controlled-reagent-release technology. | 2001 Dec |
|
| Interaction of lidocaine with reactive oxygen and nitrogen species. | 2001 Dec |
|
| Protection by glutathione of neutrophils against the toxic effects of peritoneal dialysis fluid. | 2001 Dec |
|
| A chemiluminescence reaction between hydrogen peroxide and acetonitrile and its applications. | 2001 Dec 15 |
|
| Chemiluminescence of luminol in the presence of iron(II) and oxygen: oxidation mechanism and implications for its analytical use. | 2001 Dec 15 |
|
| Cooperation of chloroquine and blood platelets in inhibition of polymorphonuclear leukocyte chemiluminescence. | 2001 Dec 15 |
|
| Ultrasensitive chemiluminescence detection of sub-fM level Co(II) in capillary electrophoresis. | 2001 Dec 21 |
|
| Effects of methoxylation of apocynin and analogs on the inhibition of reactive oxygen species production by stimulated human neutrophils. | 2001 Dec 21 |
|
| Inhibition of phosphatidylinositol 4-kinase results in a significant reduced respiratory burst in formyl-methionyl-leucyl-phenylalanine-stimulated human neutrophils. | 2001 Dec 28 |
|
| Effects of inhibitors on chicken polymorphonuclear leukocyte oxygenation activity measured by use of selective chemiluminigenic substrates. | 2001 Feb |
|
| Is homocysteine a pro-oxidant? | 2001 Nov |
|
| Chemiluminescence flow sensor for folic acid with immobilized reagents. | 2001 Nov |
|
| Luminol chemiluminescence in unbuffered solutions with a cobalt(II)-ethanolamine complex immobilized on resin as catalyst and its application to analysis. | 2001 Nov 1 |
|
| Blood transfusions impair anastomotic wound healing, reduce luminol-dependent chemiluminescence, and increase interleukin-8. | 2001 Nov-Dec |
|
| Changes in phagocyte activity in patients with ischaemic stroke. | 2001 Nov-Dec |
|
| A comparative study of bovine blood and milk neutrophil functions with luminol-dependent chemiluminescence. | 2001 Nov-Dec |
|
| Flow-through chemiluminescence sensor using immobilized histamine oxidase from Arthrobacter crystallopoietes KAIT-B-007 and peroxidase for selective determination of histamine. | 2001 Oct |
|
| Biomaterials for molecular electronics development of optical biosensor for retinol. | 2001 Oct-Dec |
|
| Flow-injection electrogenerated chemiluminescence determination of isoniazid using luminol. | 2001 Sep |
|
| Altered prostanoid production by fibroblasts cultured from the lungs of human subjects with idiopathic pulmonary fibrosis. | 2002 |
|
| Proinflammatory activity of TWEAK on human dermal fibroblasts and synoviocytes: blocking and enhancing effects of anti-TWEAK monoclonal antibodies. | 2002 |
|
| Role of Helicobacter pylori CagA+ infection in determining oxidative DNA damage in gastric mucosa. | 2002 Apr |
|
| Smoking induces oxidative stress inside the Graafian follicle. | 2002 Apr |
|
| Increased free radical production in hypertension due to increased expression of the NADPH oxidase subunit p22(phox) in lymphoblast cell lines. | 2002 Apr |
|
| Study of expression of myelin basic proteins (MBPs) in developing rat brain using a novel antibody reacting with four major isoforms of MBP. | 2002 Apr 1 |
|
| Macrophage activation includes high intracellular myeloperoxidase activity. | 2002 Apr 12 |
|
| Enhanced chemiluminescence for the oxidation of luminol with m-chloroperoxybenzoic acid catalyzed by microperoxidase 8. | 2002 Feb |
|
| Activation of phagocytic cell NADPH oxidase by norfloxacin: a potential mechanism to explain its bactericidal action. | 2002 Feb |
|
| Chemiluminescence assay for uric acid in human serum and urine using flow-injection with immobilized reagents technology. | 2002 Jan |
|
| Dioxin increases reactive oxygen production in mouse liver mitochondria. | 2002 Jan 1 |
|
| [Enhancement of luminol-dependent chemiluminescence in an aqueous NaCl/H2O2 solution by argon]. | 2002 Jan-Feb |
|
| [Chemiluminescence in oxidation of luminol by chloramine derivatives of biogenic compounds]. | 2002 Jan-Feb |
|
| In vitro monitoring sub-nanogram amounts analgin in human urine by its inhibitory of the luminol-periodate chemiluminescence reaction using reagent immobilization release technique. | 2002 Jul |
|
| Differential particulate air pollution induced oxidant stress in human granulocytes, monocytes and alveolar macrophages. | 2002 Jun |
|
| Plant tissue-based chemiluminescence flow biosensor for determination of unbound dopamine in rabbit blood with on-line microdialysis sampling. | 2002 Jun |
|
| Kinetic considerations on the electrogenerated luminescence of luminol at platinum electrode in the presence of hydrogen peroxide and oxygen. | 2002 Mar |
|
| Reactive oxygen species (ROS) production by amoebocytes of Asterias rubens (Echinodermata). | 2002 Mar |
|
| Estradiol, testosterone, dehydroepiandrosterone and androstenedione: novel derivatives and enantiomers. Interactions with rat liver microsomal cytochrome P450 and antioxidant/radical scavenger activities in vitro. | 2002 Mar 10 |
|
| Luminol-type chemiluminescence derivatization reagents for liquid chromatography and capillary electrophoresis. | 2002 Mar 15 |
|
| [Kinetic characteristics of luminol chemiluminescence caused by chloramine compounds]. | 2002 Mar-Apr |
|
| Carbon dioxide effects on luminol and 1,10-phenanthroline chemiluminescence. | 2002 May 1 |
|
| Determination of picomole amounts of thiamine through flow-injection analysis based on the suppression of luminol-KIO(4) chemiluminescence system. | 2002 May 15 |
|
| Is the neutrophil reactive oxygen species production measured by luminol and lucigenin chemiluminescence intra or extracellular? Comparison with DCFH-DA flow cytometry and cytochrome c reduction. | 2002 May 7 |
Patents
Sample Use Guides
Intraperitoneal injection of luminol (5-amino-2,3-dihydro-1,4-phthalazinedione, sodium salt) enables detection of acute inflammation largely mediated by tissue-infiltrating neutrophils. While the animal is still under anesthesia, intraperitoneally (i.p.) inject the luminol solution (10 mg/ml) for acute inflammation imaging. The final dosage is 100 mg/kg for luminol.
Route of Administration:
Intraperitoneal
Presumptive test for blood: Sodium perborate (3.5 g of Aldrich product number 24,412-0) is added to 500 mL distilled water and thoroughly dissolved. Sodium carbonate (25 g) and luminol (9.5 g) are then added and dissolved. The solution is allowed to stand for five minutes to allow any undissolved chemicals to settle. The solution is then decanted into a plastic spray bottle and is ready to use. It should be applied as a fine mist on the surface to be tested. True bloodstains will luminesce with an even glow that will last for several seconds; for better viewing, the scene should be as dark as possible.
It is significant to note that this test is only presumptive, since it is the iron in the heme which catalyzes the oxidation and subsequent light emission. The presence of copper as a contaminant will accelerate oxidation. Try the spray on a freshly cleaned copper penny.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:12:16 UTC 2023
by
admin
on
Fri Dec 15 19:12:16 UTC 2023
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| Record UNII |
5EXP385Q4F
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID5024504
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5064
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LUMINOL
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300000036126
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5EXP385Q4F
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m6930
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PRIMARY | Merck Index |
| Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
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