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Details

Stereochemistry ACHIRAL
Molecular Formula C6H7NO
Molecular Weight 109.1259
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of P-AMINOPHENOL

SMILES

NC1=CC=C(O)C=C1

InChI

InChIKey=PLIKAWJENQZMHA-UHFFFAOYSA-N
InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2

HIDE SMILES / InChI

Molecular Formula C6H7NO
Molecular Weight 109.1259
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

p-Aminophenol is an active metabolite of paracetamol. p-Aminophenol is conjugated with arachidonic acid by fatty acid amide hydrolase to form AM404. AM404 exerts effect through cannabinoid receptors. p- Aminophenol is a nephrotoxic metabolite of paracetamol and phenacetin. It causes acute renal proximal tubular necrosis after administration to rats. p-Aminophenol may cause skin sensitization, dermatitis. p-Aminophenol is a synthetic dye used in hair coloring.

Approval Year

Targets
PubMed

PubMed

TitleDatePubMed
The degradation of paracetamol (4-hydroxyacetanilide) and other substituted acetanilides by a Penicillium species.
1975
Degradation of p-nitrophenol in a batch biofilter under sequential anaerobic/aerobic environments.
2001
Analysis of the metabolites of the sodium salt of 6-hydroxy-5-(phenylazo)-2-naphthalenesulfonic acid in Sprague-Dawley rat urine.
2001 Apr 25
Contact anaphylaxis due to para-aminophenol and para-methylaminophenol in hair dye.
2001 Dec
Patch testing by additional series of allergens: results of further experiences.
2001 Dec
Potentiation of antitumor immunity by antibody-directed enzyme prodrug therapy.
2001 Dec 15
Peroxidase-catalyzed co-oxidation of 3,3',5,5'-tetramethylbenzidine with 2-amino-4-nitrophenol, 4,4'-dihydroxydiphenylsulfone, and their polydisulfides in aqueous and micellar media.
2001 Jun
Study of a novel cationic calix[4]arene used a selectivity modifier in capillary electrophoresis with electrochemical detection.
2001 Mar 2
Chloroform-soluble schiff-base Zn(II) or Cd(II) complexes from a dynamic combinatorial library.
2001 Mar 26
Enantiospecific synthesis of the proposed structure of the antitubercular marine diterpenoid pseudopteroxazole: revision of stereochemistry.
2001 May 16
Electrochemical enzyme immunoassays on microchip platforms.
2001 Nov 1
Determination of 4-aminophenol impurities in selected pharmaceutical preparations by HPLC method with amperometric detection.
2001 Sep-Oct
[Various mechanisms of the depriming effect of bacterial endotoxin on drug metabolism].
2001 Sep-Oct
Renal PGE2 production in the human and rat following phenacetin, acetaminophen and p-aminophenol.
2002
Synthesis and beta 1-, beta 2-adrenergic receptor binding studies of 4-acylamino-substituted phenoxypropanolamine and 5-acylamino-substituted naphthyloxypropanolamine derivatives.
2002
An in-vitro study of the effects of various disinfectants on prosthetic and surface materials.
2002 Apr
The spectrum of allergic (cross-)sensitivity in clinical patch testing with 'para amino' compounds.
2002 Apr
A glucose dehydrogenase biosensor as an additional signal amplification step in an enzyme-flow immunoassay.
2002 Aug
Advanced oxidation chemistry of paracetamol. UV/H(2)O(2)-induced hydroxylation/degradation pathways and (15)N-aided inventory of nitrogenous breakdown products.
2002 Aug 23
Liver regeneration is an angiogenesis- associated phenomenon.
2002 Dec
GDH biosensor based off-line capillary immunoassay for alkylphenols and their ethoxylates.
2002 Dec
A physiochemical mechanism of hemozoin (beta-hematin) synthesis by malaria parasite.
2002 Jan 11
Pyrolysis of p-benzosemiquinone.
2002 Jan 11
Cytokinin oxidase/cytokinin dehydrogenase assay: optimized procedures and applications.
2002 Jul 1
NMR and Bayesian regularized neural network regression for impurity determination of 4-aminophenol.
2002 Jul 1
Determination of the rate constants and activation energy of acetaminophen hydrolysis by capillary electrophoresis.
2002 Jul 31
Determination of 4-aminophenol using the quartz crystal microbalance sensor.
2002 Mar
Simultaneous LC determination of paracetamol and related compounds in pharmaceutical formulations using a carbon-based column.
2002 Mar 1
PISA. The effect of paracetamol (acetaminophen) and ibuprofen on body temperature in acute stroke: protocol for a phase II double-blind randomised placebo-controlled trial [ISRCTN98608690].
2002 Mar 27
Anti-tumour activity and toxicity of the new prodrug 9-aminocamptothecin glucuronide (9ACG) in mice.
2002 May 20
Deviceless decoupled electrochemical detection of catecholamines in capillary electrophoresis using gold microband array electrodes.
2002 Nov
Rapid and quantitative determination of metabolites from multiple cytochrome P450 probe substrates by gradient liquid chromatography-electrospray ionization-ion trap mass spectrometry.
2002 Nov 25
Novel electrochemical immunosensors for seafood toxin analysis.
2002 Sep
Immobilizing a single pybox ligand onto a library of solid supports.
2003
Reversible and irreversible inhibitory activity of succinic and maleic acid derivatives on acetylcholinesterase.
2003 Apr
Metalloantimalarials: targeting of P. falciparum strains with novel iron(III) and gallium(III) complexes of an amine phenol ligand.
2003 Apr 7
Immobilized enzyme-linked DNA-hybridization assay with electrochemical detection for Cryptosporidium parvum hsp70 mRNA.
2003 Aug 1
Synthesis and activity of novel benzoxazole derivatives of mannopeptimycin glycopeptide antibiotics.
2003 Aug 4
Continuous biotransformation and removal of nitrophenols under denitrifying conditions.
2003 Jul
Validation of a method for quantification of ketobemidone in human plasma with liquid chromatography-tandem mass spectrometry.
2003 Jun 15
A potential biomarker of kidney damage identified by proteomics: preliminary findings.
2003 May-Aug
First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry.
2003 Nov 5
Toxicity and human health risk of hair dyes.
2004 Apr
Degradation of 4-nitrophenol by the lignin-degrading basidiomycete Phanerochaete chrysosporium.
2004 Dec
[Kinetics and mechanism of aniline oxidation with chlorine dioxide in water].
2004 Jan
Effect of unlabeled helper probes on detection of an RNA target by bead-based sandwich hybridization.
2004 Jan
Toxic effects of aminophenols on aquatic life using the zebrafish embryo test and the comet assay.
2004 Oct
Flow injection determination of p-aminophenol at trace level using inhibited luminol-dimethylsulfoxide-NaOH-EDTA chemiluminescence.
2005 Jan-Feb
Patents

Sample Use Guides

In Vitro Use Guide
Concentrations of p-aminophenol from 1 to 100 μg/ml produced significant (p < 0.05) loss of mouse cortical neuron viability at 24 hr compared to the controls.
Substance Class Chemical
Created
by admin
on Tue Oct 22 06:41:17 UTC 2019
Edited
by admin
on Tue Oct 22 06:41:17 UTC 2019
Record UNII
R7P8FRP05V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
P-AMINOPHENOL
INCI   MI  
INCI  
Official Name English
4-AMINOPHENOL
HSDB   USP-RS  
Systematic Name English
P-HYDROXYPHENYLAMINE
Common Name English
PARACETAMOL IMPURITY K [EP]
Common Name English
4-AMINOPHENOL [USP-RS]
Common Name English
4-AMINOPHENOL [HSDB]
Common Name English
CI 76550
Common Name English
4-HYDROXYBENZENAMINE
Systematic Name English
P-HYDROXYANILINE
Common Name English
P-AMINOPHENOL [MI]
Common Name English
P-AMINOPHENOL [INCI]
Common Name English
4-HYDROXYANILINE
Systematic Name English
4-HYDROXYPHENYLAMINE
Systematic Name English
NSC-1545
Code English
PHENOL, 4-AMINO-
Systematic Name English
C.I. 76550
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
204-616-2
Created by admin on Tue Oct 22 06:41:17 UTC 2019 , Edited by admin on Tue Oct 22 06:41:17 UTC 2019
PRIMARY
PUBCHEM
403
Created by admin on Tue Oct 22 06:41:17 UTC 2019 , Edited by admin on Tue Oct 22 06:41:17 UTC 2019
PRIMARY
EVMPD
SUB169709
Created by admin on Tue Oct 22 06:41:17 UTC 2019 , Edited by admin on Tue Oct 22 06:41:17 UTC 2019
PRIMARY
MERCK INDEX
M1728
Created by admin on Tue Oct 22 06:41:17 UTC 2019 , Edited by admin on Tue Oct 22 06:41:17 UTC 2019
PRIMARY Merck Index
MESH
C026729
Created by admin on Tue Oct 22 06:41:17 UTC 2019 , Edited by admin on Tue Oct 22 06:41:17 UTC 2019
PRIMARY
RXCUI
1435279
Created by admin on Tue Oct 22 06:41:17 UTC 2019 , Edited by admin on Tue Oct 22 06:41:17 UTC 2019
PRIMARY RxNorm
EPA CompTox
123-30-8
Created by admin on Tue Oct 22 06:41:17 UTC 2019 , Edited by admin on Tue Oct 22 06:41:17 UTC 2019
PRIMARY
HSDB
123-30-8
Created by admin on Tue Oct 22 06:41:17 UTC 2019 , Edited by admin on Tue Oct 22 06:41:17 UTC 2019
PRIMARY
WIKIPEDIA
4-AMINOPHENOL
Created by admin on Tue Oct 22 06:41:17 UTC 2019 , Edited by admin on Tue Oct 22 06:41:17 UTC 2019
PRIMARY
CAS
123-30-8
Created by admin on Tue Oct 22 06:41:17 UTC 2019 , Edited by admin on Tue Oct 22 06:41:17 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY