67992-45-4

Basic information

• Product Name: dopaminechrome
• Synonyms: 2,3-Dihydro-1H-indole-5,6-dione;Aminochrome;Dopaminochrome;Indoline-5,6-dione;dopaminechrome
• CAS NO: 67992-45-4
• Molecular Formula: C₈H₇NO₂
• Molecular Weight: 149.14668
• Mol File: 67992-45-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 323.7°Cat760mmHg
• Flash Point: 160.1°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 0.000258mmHg at 25°C
• Refractive Index: 1.599
• PKA: 4.37±0.20(Predicted)
• CAS DataBase Reference: dopaminechrome(CAS DataBase Reference)
• NIST Chemistry Reference: dopaminechrome(67992-45-4)
• EPA Substance Registry System: dopaminechrome(67992-45-4)

Safety Data

• Hazardous Substances Data: 67992-45-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h3-4,9H,1-2H2

Upstream product

• 51-61-6 dopamine 
• 62-31-7 dopamine hydrochloride 

Relevant articles and documents

Regulatory Activities of Dopamine and Its Derivatives towards Metal-Free and Metal-Induced Amyloid-β Aggregation, Oxidative Stress, and Inflammation in Alzheimer's Disease

A catecholamine neurotransmitter, dopamine (DA), is suggested to be linked to the pathology of dementia; however, the involvement of DA and its structural analogues in the pathogenesis of Alzheimer's disease (AD), the most common form of dementia, composed of multiple pathogenic factors has not been clear. Herein, we report that DA and its rationally designed structural derivatives (1-6) based on DA's oxidative transformation are able to modulate multiple pathological elements found in AD [i.e., metal ions, metal-free amyloid-β (Aβ), metal-bound Aβ (metal-Aβ), and reactive oxygen species (ROS)], with demonstration of detailed molecular-level mechanisms. Our multidisciplinary studies validate that the protective effects of DA and its derivatives on Aβ aggregation and Aβ-mediated toxicity are induced by their oxidative transformation with concomitant ROS generation under aerobic conditions. In particular, DA and the derivatives (i.e., 3 and 4) show their noticeable anti-amyloidogenic ability towards metal-free Aβ and/or metal-Aβ, verified to occur via their oxidative transformation that facilitates Aβ oxidation. Moreover, in primary pan-microglial marker (CD11b)-positive cells, the major producers of inflammatory mediators in the brain, DA and its derivatives significantly diminish inflammation and oxidative stress triggered by lipopolysaccharides and Aβ through the reduced induction of inflammatory mediators as well as upregulated expression of heme oxygenase-1, the enzyme responsible for production of antioxidants. Collectively, we illuminate how DA and its derivatives can prevent multiple pathological features found in AD with identification of molecular-level mechanisms. The overall studies could advance our understanding regarding distinct roles of neurotransmitters in AD and identify key interactions for alleviation of AD pathology.

The participation of Singlet Oxygen in Dye-Sensitized Photooxidation Reaction of Catecholamines

The photooxidation of catecholamines (adrenaline, noradrenaline and dopamine) sensitized by methylene blue (MB), rose bengal (RB) and fluoresceine (FL) proceed via aminochromes and an indolic pathway.In D2O rate constants of sensitized photooxidation are increased for about 2,7 times over rates in water. 1,3-diphenylisobenzofuran (DPBF), 1,4-diazobicyclooctane (DABCO) and azide anion were more effective inhibitors of the reaction in D2O than in H2O.Superoxide dismutase markedly decreases the rates of photooxidation in H2O and in D2O.Isotope effects and 1O2-quenchers sensitivities indicate that singlet oxygen participates on photooxidation processes of catecholamines.