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Merck
CN

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:
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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

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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Cardiotoxicity of adrenochrome in isolated rabbit hearts assessed by epicardial NADH fluorescence.
Rump AF, et al.
Archives of Toxicology, 68, 571-571 (1994)
Effect of Bacillus coagulans and B. firmus incorporated probiotic diet on Superoxide dismutase activity and catalase activity in Penaeus monodon.
Raghu P, et al.
World Scientific News, 44, 224-224 (2016)
Towards an adrenaline biosensor based on substrate recycling amplification in combination with an enzyme logic gate.
Molinnus D, et al.
Sensors and Actuators B, Chemical, 237, 190-195 (2016)
Ventricular dysfunction and necrosis produced by adrenochrome metabolite of epinephrine: relation to pathogenesis of catecholamine cardiomyopathy.
Yates JC, et al.
American Heart Journal, 102, 210-210 (1981)
Zhimin Tao et al.
Langmuir : the ACS journal of surfaces and colloids, 25(17), 10183-10188 (2009-05-27)
We have measured the influence of mesoporous silica (MCM-41 and SBA-15) nanoparticles and dense silica nanoparticles on epinephrine oxidation, a pH-dependent reaction, whose rate is small in acidic or neutral solutions but much greater at higher pH. The reaction was

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