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Details

Stereochemistry ACHIRAL
Molecular Formula C6H7NO
Molecular Weight 109.1259
Optical Activity NONE
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 No
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

2013
530
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
656
Substrate
656
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Isolation and characterization of a pseudomonas strain that degrades 4-acetamidophenol and 4-aminophenol.
2001
Contact anaphylaxis due to para-aminophenol and para-methylaminophenol in hair dye.
2001 Dec
Determination of 4-aminophenol impurities in selected pharmaceutical preparations by HPLC method with amperometric detection.
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
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
[Research into simultaneous spectrophotometric determination of components in cough syrup by principal component regression method].
2002 Jun
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
Cross-sensitization to haptens: formation of common haptenic metabolites, T cell recognition of cryptic peptides, and true T cell cross-reactivity.
2002 May
Anti-tumour activity and toxicity of the new prodrug 9-aminocamptothecin glucuronide (9ACG) in mice.
2002 May 20
Design and synthesis of aminophenol-based factor Xa inhibitors.
2002 May 6
Deviceless decoupled electrochemical detection of catecholamines in capillary electrophoresis using gold microband array electrodes.
2002 Nov
Biological activity of p-methylaminophenol, an essential structural component of N-(4-hydroxyphenyl)retinamide, fenretinide.
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
The use of thermal lensing for the determination of pyrogens.
2003 Apr
Generation of ligand conformations in continuum solvent consistent with protein active site topology: application to thrombin.
2003 Apr 10
Metalloantimalarials: targeting of P. falciparum strains with novel iron(III) and gallium(III) complexes of an amine phenol ligand.
2003 Apr 7
Evolution of catabolic pathways for synthetic compounds: bacterial pathways for degradation of 2,4-dinitrotoluene and nitrobenzene.
2003 Aug
Synthesis and activity of novel benzoxazole derivatives of mannopeptimycin glycopeptide antibiotics.
2003 Aug 4
A capillary-based amperometric flow immunoassay for 2,4,6-trichlorophenol.
2003 Jan
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
Enzyme-amplified electrochemical detection of DNA using electrocatalysis of ferrocenyl-tethered dendrimer.
2003 Nov 1
First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry.
2003 Nov 5
A new dynamic electrochemical transduction mechanism for interdigitated array microelectrodes.
2004 Dec
Degradation of 4-nitrophenol by the lignin-degrading basidiomycete Phanerochaete chrysosporium.
2004 Dec
Express detection of nonylphenol in water samples by fluorescence polarization immunoassay.
2004 Feb
[Kinetics and mechanism of aniline oxidation with chlorine dioxide in water].
2004 Jan
Electric chips for rapid detection and quantification of nucleic acids.
2004 Jan 15
Hair dye contact allergy: quantitative exposure assessment of selected products and clinical cases.
2004 Jun
Toxic effects of aminophenols on aquatic life using the zebrafish embryo test and the comet assay.
2004 Oct
Microchip capillary electrophoresis with a boron-doped diamond electrochemical detector for analysis of aromatic amines.
2004 Sep
Pharmacophore based synthesis of 3-chloroquinoxaline-2-carboxamides as serotonin3 (5-HT3) receptor antagonist.
2004 Sep
Automated spectrophotometric assay for urine p-aminophenol by an oxidative coupling reaction.
2004 Summer
Patents

Patents

JP1004635A
3
JP2000026572A
2
JP2000103975A
5
JP2000248077A
2
JP2001183835A
2
JP2001192500A
2
JP2001342238A
2
JP2002088066A
2
JP2002533511A
2
JP2003128513A
2
JP2005029590A
5
JP2005082628A
2
JP2005306866A
2
JP2005527113A
3
JP2006008642A
2
JP2006028082A
2
JP2006278197A
2
JP2006321834A
2
JP2006523256A
7
JP2007084524A
2
JP2007308427A
3
JP2008214479A
2
JP2009263324A
4
JP2011529977A
2
JP2012500104A
106
JP3016599B2
2
JP4550838B2
2
JP4728230B2
4
JP4820369B2
6
JPH01174526A
2
JPH01319528A
2
JPH0211551A
2
JPH02170862A
2
JPH02188556A
2
JPH0219368A
2
JPH02232224A
2
JPH02240138A
2
JPH0269448A
2
JPH03112946A
4
JPH03127762A
4
JPH03177419A
2
JPH04108824A
2
JPH04154860A
2
JPH0496924A
2
JPH05156007A
2
JPH05170902A
3
JPH05174621A
2
JPH05221937A
2
JPH0551450A
2
JPH06219999A
2
JPH06228303A
2
US3079435 A
2

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Thu Jul 06 00:22:14 UTC 2023
Edited
by admin
on Thu Jul 06 00:22:14 UTC 2023
Record UNII
R7P8FRP05V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
P-AMINOPHENOL
INCI   MI  
INCI  
Official Name English
4-AMINOPHENOL [USP IMPURITY]
Common Name English
4-AMINOPHENOL
HSDB   USP-RS  
Systematic Name English
P-HYDROXYPHENYLAMINE
Common Name English
PARACETAMOL IMPURITY K [EP IMPURITY]
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
MESALAZINE IMPURITY A [EP IMPURITY]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
204-616-2
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
NSC
1545
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
PUBCHEM
403
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
DAILYMED
R7P8FRP05V
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
DRUG BANK
DB14144
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
EVMPD
SUB169709
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
RS_ITEM_NUM
1021204
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
MERCK INDEX
M1728
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY Merck Index
MESH
C026729
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
RXCUI
1435279
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY RxNorm
FDA UNII
R7P8FRP05V
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID3024499
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
HSDB
2640
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
WIKIPEDIA
4-AMINOPHENOL
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
CHEBI
17602
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
CAS
123-30-8
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
SMS_ID
100000159523
Created by admin on Thu Jul 06 00:22:14 UTC 2023 , Edited by admin on Thu Jul 06 00:22:14 UTC 2023
PRIMARY
Related Record Type Details
Structure of P-AMINOPHENOL SULFATE
SALT/SOLVATE -> PARENT
Structure of P-AMINOPHENOL HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of ACETAMINOPHEN
PARENT -> METABOLITE ACTIVE
May be substrate for formation of AM-404
MINOR
Related Record Type Details
Structure of MESALAMINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of MESALAMINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
USP
Structure of ACETAMINOPHEN
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of P-AMINOPHENOL
ACTIVE MOIETY
NIH
NCATS
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