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Details

Stereochemistry ACHIRAL
Molecular Formula C8H7N3O2
Molecular Weight 177.1604
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LUMINOL

SMILES

c1cc2c(c(c1)N)c(nnc2O)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)

HIDE SMILES / InChI

Molecular Formula C8H7N3O2
Molecular Weight 177.1604
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

PubMed

TitleDatePubMed
Insulin-induced peroxynitrite production in human platelet-rich plasma.
2001
The antioxidant activity of BHT and new phenolic compounds PYA and PPA measured by chemiluminescence.
2001
Anticonvulsive and free radical scavenging activities of Gastrodia elata Bl. in kainic acid-treated rats.
2001
Menadione-catalyzed O2- production by Escherichia coli cells: application of rapid chemiluminescent assay to antimicrobial susceptibility testing.
2001
Immunomodulation by exogenous surfactant: effect on TNF-alpha secretion and luminol-enhanced chemiluminescence activity by murine macrophages stimulated with group B streptococci.
2001 Apr
In vitro effect of different non-steroidal anti-inflammatory drugs on human polymorphonuclear leukocyte activity measured by luminol-dependent chemiluminescence of the whole blood.
2001 Apr
Evaluation of total reactive antioxidant potential (TRAP) of tissue homogenates and their cytosols.
2001 Apr 15
Different kinds of reactive oxygen and nitrogen species were detected in colon and breast tumors.
2001 Apr 26
Nitric oxide and endothelin relationship in intestinal ischemia/reperfusion injury (II).
2001 Apr-May
Reagentless chemiluminescence flow sensor for the determination of riboflavin in pharmaceutical preparations and human urine.
2001 Aug
Determination of the oxidative burst chemiluminescent response of avian and murine-derived macrophages versus corresponding cell lines in relation to stimulation with Salmonella serotypes.
2001 Aug 10
Chemiluminescence in inflammatory bowel disease patients: a parameter of inflammatory activity.
2001 Aug 20
Reactive oxygen species activity, mucosal lipoperoxidation and glutathione in Helicobacter pylori-infected gastric mucosa.
2001 Dec
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
Cytochrome P450 (P450) isoforms expression, P450 concentration, monooxygenase activities, reactive oxygen species formation, lipid peroxidation, and glutathione content in wild catch carp and tench liver--influence of a two weeks exposure to phenobarbital.
2001 Feb
Chemiluminescence flow sensor for berberine with immobilized reagents.
2001 Jul
Effects of prilocaine and articaine on human leucocytes and reactive oxygen species in vitro.
2001 Jul
LLU-alpha, an endogenous metabolite of gamma-tocopherol, is more effective against metal nephrotoxicity in rats than gamma-tocopherol.
2001 Jul 6
A study of common interferences with the forensic luminol test for blood.
2001 Jul-Aug
Increased carbon disulfide-stimulated chemiluminescence in the pyrogallol-luminol system.
2001 Jul-Aug
Thiols enhance the sensitivity of luminescent assays for non-cross-linked and covalently cross-linked aminophthalhydrazides.
2001 Jul-Aug
Nitric oxide and superoxide radical production by human mononuclear leukocytes.
2001 Jun
A simple chemiluminescence-based method for rapid enumeration of Listeria spp. microcolonies.
2001 Jun
Coronary and myocardial effects of acetaminophen: protection during ischemia-reperfusion.
2001 Jun
Circulating neutrophil priming and systemic inflammation in limb ischaemia-reperfusion injury.
2001 Mar
Luminol-dependent chemiluminescence analysis of chitooligosaccharide-induced rapid production of hydrogen peroxide by intact wheat seedlings.
2001 Mar
Charge-coupled device camera-based detection of fluorescence-labeled proteins immobilized on nitrocellulose membranes.
2001 Mar
Capillary electrophoresis system with flow injection sample introduction and chemiluminescence detection on a chip platform.
2001 Mar
Plant tissue-based chemiluminescence flow biosensor for glycolic acid.
2001 Mar 15
Evaluation and comparison of two improved techniques for the on-line detection of antioxidants in liquid chromatography eluates.
2001 Mar 30
Endothelial regulation of vasomotion in apoE-deficient mice: implications for interactions between peroxynitrite and tetrahydrobiopterin.
2001 Mar 6
Application of an enhanced luminol chemiluminescence reaction using 4-[4,5-di(2-pyridyl)-1H-imidazol-2-yl]phenylboronic acid to photographic detection of horseradish peroxidase on a membrane.
2001 Mar-Apr
Electrogenerated chemiluminescence of luminol for oxidase-based fibre-optic biosensors.
2001 Mar-Apr
Long-term chemiluminescent signal is produced in the course of luminol peroxidation catalyzed by peroxidase isolated from leaves of african oil palm tree.
2001 May
Redox control of oxygen sensing in the rabbit ductus arteriosus.
2001 May 15
Increasing the specificity of the forensic luminol test for blood.
2001 May-Jun
Flow-chemiluminescence: a growing modality of pharmaceutical analysis.
2001 May-Jun
Chemiluminescence flow sensor for folic acid with immobilized reagents.
2001 Nov
Blood transfusions impair anastomotic wound healing, reduce luminol-dependent chemiluminescence, and increase interleukin-8.
2001 Nov-Dec
Antioxidative and antimutagenic activity of yeast cell wall mannans in vitro.
2001 Oct 18
Role of Helicobacter pylori CagA+ infection in determining oxidative DNA damage in gastric mucosa.
2002 Apr
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
Luminol-type chemiluminescence derivatization reagents for liquid chromatography and capillary electrophoresis.
2002 Mar 15
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:30:29 UTC 2021
Edited
by admin
on Sat Jun 26 11:30:29 UTC 2021
Record UNII
5EXP385Q4F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LUMINOL
MI  
Common Name English
O-AMINOPHTHALYLHYDRAZIDE
Common Name English
3-AMINOPHTHALIC HYDRAZIDE
Systematic Name English
O-AMINOPHTHALOYL HYDRAZIDE
Common Name English
5-AMINO-2,3-DIHYDRO-1,4-PHTHALAZINEDIONE
Systematic Name English
LUMINOL [MI]
Common Name English
NSC-5064
Code English
Code System Code Type Description
EPA CompTox
521-31-3
Created by admin on Sat Jun 26 11:30:29 UTC 2021 , Edited by admin on Sat Jun 26 11:30:29 UTC 2021
PRIMARY
CAS
521-31-3
Created by admin on Sat Jun 26 11:30:29 UTC 2021 , Edited by admin on Sat Jun 26 11:30:29 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-309-4
Created by admin on Sat Jun 26 11:30:29 UTC 2021 , Edited by admin on Sat Jun 26 11:30:29 UTC 2021
PRIMARY
PUBCHEM
10638
Created by admin on Sat Jun 26 11:30:29 UTC 2021 , Edited by admin on Sat Jun 26 11:30:29 UTC 2021
PRIMARY
WIKIPEDIA
LUMINOL
Created by admin on Sat Jun 26 11:30:29 UTC 2021 , Edited by admin on Sat Jun 26 11:30:29 UTC 2021
PRIMARY
FDA UNII
5EXP385Q4F
Created by admin on Sat Jun 26 11:30:29 UTC 2021 , Edited by admin on Sat Jun 26 11:30:29 UTC 2021
PRIMARY
MERCK INDEX
M6930
Created by admin on Sat Jun 26 11:30:29 UTC 2021 , Edited by admin on Sat Jun 26 11:30:29 UTC 2021
PRIMARY Merck Index