All Photos(2)

A5752

Sigma-Aldrich

Adrenochrome

Synonym(s):
3-Hydroxy-1-methyl-5,6-indolinedione
Empirical Formula (Hill Notation):
C9H9NO3
CAS Number:
Molecular Weight:
179.17
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.47

Quality Level

assay

>95% (HPLC)

form

powder

application(s)

hematology: suitable
histology: suitable

εmax

3-4.5 at 485-490 nm in water
9.0-10.5 at 299-304 nm in water

Featured Industry

Diagnostic Assay Manufacturing

storage temp.

−20°C

SMILES string

CN1CC(O)C2=CC(=O)C(=O)C=C12

InChI

1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3

InChI key

RPHLQSHHTJORHI-UHFFFAOYSA-N

Related Categories

Application

Adrenochrome has been used to study the effect of adrenochrome on coronary artery constriction in the rat heart.

Packaging

25, 250 mg in glass insert

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A5752.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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 oxidative metabolism of catecholamines in the brain: a review.
Smythies J and Galzigna L
Biochimica et Biophysica Acta, 1380, 159-159 (1998)
Vera Marisa Costa et al.
Chemical research in toxicology, 20(8), 1183-1191 (2007-07-17)
High concentrations of circulating biogenic catecholamines often exist during the course of several cardiovascular disorders. Additionally, coronary dysfunctions are prominent and frequently related to the ischemic and reperfusion phenomenon (I/R) in the heart, which leads to the release of large...
The adrenochrome hypothesis of schizophrenia revisited.
Smythies J
Neurotoxicity Research, 4, 147-147 (2002)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service