49607-15-0

Basic information

• Product Name: 3-NITROTYRAMINE
• Synonyms: 3-NITROTYRAMINE;Phenol, 4-(2-aMinoethyl)-2-nitro-
• CAS NO: 49607-15-0
• Molecular Formula: C₈H₁₀N₂O₃
• Molecular Weight: 182.18
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 49607-15-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 217 °C (decomp)
• Boiling Point: 326.785°C at 760 mmHg
• Flash Point: 151.434°C
• Appearance: /
• Density: 1.338g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 6.53±0.35(Predicted)
• CAS DataBase Reference: 3-NITROTYRAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-NITROTYRAMINE(49607-15-0)
• EPA Substance Registry System: 3-NITROTYRAMINE(49607-15-0)

Safety Data

• Hazardous Substances Data: 49607-15-0(Hazardous Substances Data)

Usage

General Description

3-NITROTYRAMINE is a chemical compound that is formed through the nitration of the amino acid tyramine. It is a nitroaryl compound with a nitro group attached to the aromatic ring. 3-NITROTYRAMINE has been studied for its potential pharmacological effects, particularly in relation to its role as a neurotransmitter and its impact on the central nervous system. It is also being investigated for its potential use in the treatment of neurological disorders. Additionally, 3-NITROTYRAMINE has been identified as a biomarker for oxidative stress and is associated with various pathological conditions, making it an important molecule for medical research and diagnostics.

InChI:InChI=1/C8H10N2O3/c9-4-3-6-1-2-8(11)7(5-6)10(12)13/h1-2,5,11H,3-4,9H2

Upstream product

• 51-67-2 tyrosamine 
• 7697-37-2 nitric acid 
• 60-19-5 tyramine hydrochloride 

Downstream Products

• 49640-22-4 2-(4-(benzyloxy)-3-nitrophenyl)ethanamine 
• 81666-88-8 3-amino-4-hydroxyphenylethylamine 

Relevant articles and documents

An Azo Coupling Strategy for Protein 3-Nitrotyrosine Derivatization

Herein, a strategy for the selective derivatization of 3-nitrotyrosine-containing proteins using the classic azo coupling reaction as the key step is described. This novel approach featured multiple advantages and was successfully applied to detect picomole levels of protein tyrosine nitration in biological samples.

Reduction of the nitro group to amine by hydroiodic acid to synthesize o-aminophenol derivatives as putative degradative markers of neuromelanin

Neuromelanin (NM) is produced in dopaminergic neurons of the substantia nigra (SN) and in noradrenergic neurons of the locus coeruleus (LC). The synthesis of NM in those neurons is a component of brain aging and there is the evidence that this pigment can be involved in the pathogenesis of neurodegenerative diseases such as Parkinson's disease. NM is believed to derive from the oxidative polymerization of dopamine (DA) or norepinephrine (NE) with the participation of cysteine, dolichols and proteins. However, there are still unknown aspects in the chemical structure of NM from SN (SN-NM) and LC (LC-NM). In this study, we designed a new method to synthesize o-aminophenol compounds as putative degradation products of catecholamines and their metabolites which may be incorporated into NM. Those compounds are aminohydroxyphenylethylamine (AHPEA) isomers, aminohydroxyphenylacetic acid (AHPAA) isomers and aminohydroxyethylbenzene (AHEB) isomers, which are expected to arise from DA or NE, 3,4-dihydroxyphenylacetic acid (DOPAC) or 3,4-dihydroxyphenylmandelic acid (DOMA) and 3,4-dihydroxyphenylethanol (DOPE) or 3,4- dihydroxyphenylethyleneglycol (DOPEG), respectively. These o-aminophenol compounds were synthesized by the nitration of phenol derivatives followed by reduction with hydroiodic acid (HI), and they could be identified by HPLC in HI hydrolysates of SN-NM and LC-NM. This degradative approach by HI hydrolysis allows the identification of catecholic precursors unique to SN-NM and LC-NM, which are present in catecholaminergic neurons.