A5752
Adrenochrome
>95% purity (HPLC), powder
Synonym(s):
3-Hydroxy-1-methyl-5,6-indolinedione
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About This Item
Empirical Formula (Hill Notation):
C9H9NO3
CAS Number:
Molecular Weight:
179.17
NACRES:
NA.47
PubChem Substance ID:
UNSPSC Code:
12171500
EC Number:
200-192-8
MDL number:
Product Name
Adrenochrome, ≥95% (HPLC)
InChI key
RPHLQSHHTJORHI-UHFFFAOYSA-N
InChI
1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3
SMILES string
CN1CC(O)C2=CC(=O)C(=O)C=C12
assay
≥95% (HPLC)
form
powder
color
red to brown
εmax
3-4.5 at 485-490 nm in water, 9.0-10.5 at 299-304 nm in water
application(s)
diagnostic assay manufacturing
hematology
histology
storage temp.
−20°C
Quality Level
Related Categories
Application
Adrenochrome has been used to study the effect of adrenochrome on coronary artery constriction in the rat heart.
Biochem/physiol Actions
Adrenochrome is an oxidation product of adrenaline. It has been implicated in cardiotoxicity. It is a short-lived cytotoxic molecule and is part of the leukocyte response used to kill bacteria. Adrenochrome is also suggested to exhibit psychotomimetic effects. It is used to determine superoxide dismutase activity.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Maria Luisa Genova et al.
Archives of biochemistry and biophysics, 447(2), 167-173 (2006-02-21)
Complex I in bovine heart submitochondrial particles catalyses the NADH-supported generation of superoxide anion; adrenaline is oxidised by superoxide to adrenochrome that, on its hand, is reduced by Complex I, thus establishing a redox cycle that amplifies the superoxide production.
Adrenochrome-induced coronary artery constriction in the rat heart.
Karmazyn M, et al.
Journal of Pharmacology and Experimental Therapeutics, 219, 225-225 (1981)
Viviana S Fluxá et al.
Nature protocols, 3(8), 1270-1277 (2008-08-21)
The adrenaline test for enzymes is a colorimetric enzyme assay based on the quantification of periodate-sensitive reaction products such as 1,2-diols and 1,2-aminoalcohols by back-titration of the oxidant with adrenaline to produce adrenochrome as an easily detectable red product. The
Janna Shainsky et al.
Applied and environmental microbiology, 75(14), 4711-4719 (2009-05-26)
Enantiopure sulfoxides are prevalent in drugs and are useful chiral auxiliaries in organic synthesis. The biocatalytic enantioselective oxidation of prochiral sulfides is a direct and economical approach for the synthesis of optically pure sulfoxides. The selection of suitable biocatalysts requires
The adrenochrome hypothesis of schizophrenia revisited.
Smythies J
Neurotoxicity Research, 4, 147-147 (2002)
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