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Details

Stereochemistry ACHIRAL
Molecular Formula C6H7NO
Molecular Weight 109.1261
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of P-AMINOPHENOL

SMILES

c1cc(ccc1N)O

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 109.1261
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
520
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
609
Substrate
609
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
The degradation of paracetamol (4-hydroxyacetanilide) and other substituted acetanilides by a Penicillium species.
1975
Analysis of the metabolites of the sodium salt of 6-hydroxy-5-(phenylazo)-2-naphthalenesulfonic acid in Sprague-Dawley rat urine.
2001 Apr 25
Patch testing by additional series of allergens: results of further experiences.
2001 Dec
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
Small volume bead assay for ovalbumin with electrochemical detection.
2001 Mar
Quantitative analysis of analgoantipyretics in dosage form using planar chromatography.
2001 Mar
Study of a novel cationic calix[4]arene used a selectivity modifier in capillary electrophoresis with electrochemical detection.
2001 Mar 2
Enantiospecific synthesis of the proposed structure of the antitubercular marine diterpenoid pseudopteroxazole: revision of stereochemistry.
2001 May 16
[Various mechanisms of the depriming effect of bacterial endotoxin on drug metabolism].
2001 Sep-Oct
Effects of alternative carbon sources on biological transformation of nitrophenols.
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
Liver regeneration is an angiogenesis- associated phenomenon.
2002 Dec
GDH biosensor based off-line capillary immunoassay for alkylphenols and their ethoxylates.
2002 Dec
[Research into simultaneous spectrophotometric determination of components in cough syrup by principal component regression method].
2002 Jun
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
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
Sorption and diffusion of phenols onto well-defined ordered nanoporous monolithic silicas.
2003 Apr 1
Generation of ligand conformations in continuum solvent consistent with protein active site topology: application to thrombin.
2003 Apr 10
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
Determination of 4-aminophenol impurities in multicomponent analgesic preparations by HPLC with amperometric detection.
2003 Aug 8
Toxicological detection of the new designer drug 1-(4-methoxyphenyl)piperazine and its metabolites in urine and differentiation from an intake of structurally related medicaments using gas chromatography-mass spectrometry.
2003 Dec 25
Continuous biotransformation and removal of nitrophenols under denitrifying conditions.
2003 Jul
Enhancement of antioxidant activity of p-alkylaminophenols by alkyl chain elongation.
2003 Jul 31
Unbiased spectrophotometric method for estimating phenol or o-cresol in unknown water samples.
2003 Jun
Poly(ethyleneglycol) column for the determination of acetaminophen, phenylephrine and chlorpheniramine in pharmaceutical formulations.
2003 Mar 5
A potential biomarker of kidney damage identified by proteomics: preliminary findings.
2003 May-Aug
The demonstration of an enhanced microelectrochemical transistor for measurements in neutral solution at low analyte concentration.
2004 Aug
A new dynamic electrochemical transduction mechanism for interdigitated array microelectrodes.
2004 Dec
Electrical detection of viral DNA using ultramicroelectrode arrays.
2004 Feb 1
Spectrophotometric determination of paracetamol with microwave assisted alkaline hydrolysis.
2004 Jul
Scanning electrochemical microscopy of quinoprotein glucose dehydrogenase.
2004 Jun 1
Synthesis and biological activity of novel retinamide and retinoate derivatives.
2004 May
Hapten-directed targeting to single-chain antibody receptors.
2004 May
Bead-based electrochemical immunoassay for bacteriophage MS2.
2004 May 15
Reactions of arylamine and aminophenol derivatives, and riboflavin with organic radicals.
2004 Nov
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
Flow injection determination of p-aminophenol at trace level using inhibited luminol-dimethylsulfoxide-NaOH-EDTA chemiluminescence.
2005 Jan-Feb
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 Sat Jun 26 05:45:18 UTC 2021
Edited
by admin
on Sat Jun 26 05:45:18 UTC 2021
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
4-AMINOPHENOL [USP]
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]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
204-616-2
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
PRIMARY
PUBCHEM
403
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
PRIMARY
DRUG BANK
DB14144
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
PRIMARY
EVMPD
SUB169709
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
PRIMARY
MERCK INDEX
M1728
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
PRIMARY Merck Index
MESH
C026729
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
PRIMARY
RXCUI
1435279
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
PRIMARY RxNorm
FDA UNII
R7P8FRP05V
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
PRIMARY
EPA CompTox
123-30-8
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
PRIMARY
USP_CATALOG
1021204
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
PRIMARY USP-RS
HSDB
2640
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
PRIMARY
WIKIPEDIA
4-AMINOPHENOL
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
PRIMARY
CAS
123-30-8
Created by admin on Sat Jun 26 05:45:19 UTC 2021 , Edited by admin on Sat Jun 26 05:45:19 UTC 2021
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 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)
EP
Related Record Type Details
Structure of P-AMINOPHENOL
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