ADRENOCHROME

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C9H9NO3
Molecular Weight	179.1727
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28392416 | https://www.ncbi.nlm.nih.gov/pubmed/25855923

Adrenochrome is a member of a class of chemicals known as aminochromes, each one derived by the oxidation of its precursor amine. Adrenochrome was proposed for the biogenesis of schizophrenia in 1952. Since that time the adrenochrome theory has been one of the most established and discussed theories in this field. It is known, that adrenochrome is toxic to myocar-dial tissue and may be responsible for fibril-lation and sudden death under stress. Aminochrome has been suggested as a physiological preclinical model capable of inducing five of the six mechanisms of Parkinson's disease. Until now, there is no evidence that aminochrome induces glial activation related to neuroinflammation, an important mechanism involved in the loss of dopaminergic neurons, but was shown, aminochrome neuroinflammatory ability and supported the hypothesis that it might be a better PD preclinical model to find new pharmacological treatment that stop the development of this disease.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
The inhibitory effects of adrenochrome on cell metabolism.	1948 Apr	18910690
Adrenochrome and related compounds.	1972	4581204
Hallucinogens as hard science: the adrenochrome hypothesis for the biogenesis of schizophrenia.	2010 May	20533770
Adrenochrome and related oxidative metabolites of catecholamines: effects on dopamine neurons and receptor binding profiles.	2011 Dec	21906912
Niacin-respondent subset of schizophrenia – a therapeutic review.	2015	25855923
The chemical interaction between adrenochrome, three different classes of antipsychotic drugs and metabolites of the kynurenine pathway.	2015 Mar	25554565

Patents

Sample Use Guides

In Vivo Use Guide

In rats

Route of Administration: Intraperitoneal

In Vitro Use Guide

Aminochrome was found to be toxic in a mouse-derived neuronal cell line (CNh). The effect was concentration dependent (10-150 microM). The issue whether aminochrome toxicity involves glutamate transmission was studied with several glutamate receptors antagonists. Incubation of the cells with aminochrome (150 microM) in the presence of 100 microM of the AMPA antagonist, NBQX resulted in an increase of cell survival, from 52 to 73%. However, this protective effect did not seem to be related to activation of ionotropic glutamate receptors since incubation of CNh cells with 200 microM of glutamate resulted in only 10% decrease of cell survival. However, NBQX was found to inhibit in vitro the autoxidation process. One hundred microM AP-5 did not have any effect on aminochrome toxicity. The toxic effect of aminochrome on CNh cells seems to be dependent of extracellular activation since addition of dicoumarol, a specific inhibitor of DT-diaphorase, did not affect that toxicity, which can be explained perhaps by a lack of a transport system for aminochrome into the CNh cells.

Name

Type

Language

ADRENOCHROME

Common Name

English

1H-INDOLE-5,6-DIONE, 2,3-DIHYDRO-3-HYDROXY-1-METHYL-

Systematic Name

English

ADRENOCHROME [MI]

Common Name

English

ADRAXONE

Common Name

English

3-HYDROXY-1-METHYL-5,6-INDOLINEDIONE

Systematic Name

English

2,3-DIHYDRO-3-HYDROXY-1-METHYL-1H-INDOLE-5,6-DIONE

Systematic Name

English

Code System Code Type Description

CAS

54-06-8