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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 of ADRENOCHROME

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

Molecular Formula C9H9NO3
Molecular Weight 179.1727
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
The inhibitory effects of adrenochrome on cell metabolism.
1948 Apr
Hallucinogens as hard science: the adrenochrome hypothesis for the biogenesis of schizophrenia.
2010 May
Patents

Sample Use Guides

In rats
Route of Administration: Intraperitoneal
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:02:51 UTC 2023
Edited
by admin
on Sat Dec 16 02:02:51 UTC 2023
Record UNII
70G54NQL71
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ADRENOCHROME
MI  
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
Created by admin on Sat Dec 16 02:02:51 UTC 2023 , Edited by admin on Sat Dec 16 02:02:51 UTC 2023
PRIMARY
MESH
D000323
Created by admin on Sat Dec 16 02:02:51 UTC 2023 , Edited by admin on Sat Dec 16 02:02:51 UTC 2023
PRIMARY
WIKIPEDIA
ADRENOCHROME
Created by admin on Sat Dec 16 02:02:51 UTC 2023 , Edited by admin on Sat Dec 16 02:02:51 UTC 2023
PRIMARY
PUBCHEM
5898
Created by admin on Sat Dec 16 02:02:51 UTC 2023 , Edited by admin on Sat Dec 16 02:02:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID00871530
Created by admin on Sat Dec 16 02:02:51 UTC 2023 , Edited by admin on Sat Dec 16 02:02:51 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-192-8
Created by admin on Sat Dec 16 02:02:51 UTC 2023 , Edited by admin on Sat Dec 16 02:02:51 UTC 2023
PRIMARY
MERCK INDEX
m1431
Created by admin on Sat Dec 16 02:02:51 UTC 2023 , Edited by admin on Sat Dec 16 02:02:51 UTC 2023
PRIMARY Merck Index
FDA UNII
70G54NQL71
Created by admin on Sat Dec 16 02:02:51 UTC 2023 , Edited by admin on Sat Dec 16 02:02:51 UTC 2023
PRIMARY