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 Germany

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

The oxidative metabolism of catecholamines in the brain: a review.
Smythies J and Galzigna L
Biochimica et Biophysica Acta, 1380, 159-159 (1998)
The adrenochrome hypothesis of schizophrenia revisited.
Smythies J
Neurotoxicity Research, 4, 147-147 (2002)
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...
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...
John A Mills
History of psychology, 13(2), 178-195 (2010-06-11)
Working in a psychiatrically innovative environment created by the Government of Saskatchewan, Canada, Abram Hoffer and Humphry F. Osmond enunciated the adrenochrome hypothesis for the biogenesis of schizophrenia in 1952, slightly later proposing and, apparently, demonstrating, in a double-blind study...

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