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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
589
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
661
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Renal PGE2 production in the human and rat following phenacetin, acetaminophen and p-aminophenol.
2002
Effects of alternative carbon sources on biological transformation of nitrophenols.
2002
[Research into simultaneous spectrophotometric determination of components in cough syrup by principal component regression method].
2002 Jun
Immobilizing a single pybox ligand onto a library of solid supports.
2003
The use of thermal lensing for the determination of pyrogens.
2003 Apr
Reversible and irreversible inhibitory activity of succinic and maleic acid derivatives on acetylcholinesterase.
2003 Apr
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
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
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
Synthesis of 11C-amides using [11C]carbon monoxide and in situ activated amines by palladium-mediated carboxaminations.
2003 Feb 7
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
Validation of a method for quantification of ketobemidone in human plasma with liquid chromatography-tandem mass spectrometry.
2003 Jun 15
Dlf complexes with uniform coordination geometry: structural and magnetic properties of an LnNi2 core supported by a heptadentate amine phenol ligand.
2003 Mar 10
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
Oxidation-reduction potential as a control variable for the anaerobic stage during anaerobic-aerobic p-nitrophenol degradation.
2003 Nov-Dec
Kinetics of aniline oxidation with chlorine dioxide.
2004
Toxicity and human health risk of hair dyes.
2004 Apr
Poly(dimethylsiloxane) microchip capillary electrophoresis with electrochemical detection for rapid measurement of acetaminophen and its hydrolysate.
2004 Aug
The measurement of alkaline phosphatase at nanomolar concentration within 70 s using a disposable microelectrochemical transistor.
2004 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
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
Electrical detection of viral DNA using ultramicroelectrode arrays.
2004 Feb 1
[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
Electric chips for rapid detection and quantification of nucleic acids.
2004 Jan 15
Spectrophotometric determination of paracetamol with microwave assisted alkaline hydrolysis.
2004 Jul
Hair dye contact allergy: quantitative exposure assessment of selected products and clinical cases.
2004 Jun
Bead-based immunoassays with microelectrode detection.
2004 Jun
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
Microbead-based electrochemical immunoassay with interdigitated array electrodes.
2004 May 15
Reactions of arylamine and aminophenol derivatives, and riboflavin with organic radicals.
2004 Nov
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
Flow injection determination of p-aminophenol at trace level using inhibited luminol-dimethylsulfoxide-NaOH-EDTA chemiluminescence.
2005 Jan-Feb
Patents

Patents

JP1004635A
4
JP2000026572A
3
JP2000103975A
6
JP2000248077A
3
JP2001183835A
3
JP2001192500A
3
JP2001342238A
3
JP2002088066A
3
JP2002533511A
3
JP2003128513A
3
JP2005029590A
6
JP2005082628A
3
JP2005306866A
3
JP2005527113A
4
JP2006008642A
3
JP2006028082A
3
JP2006278197A
3
JP2006321834A
3
JP2006523256A
8
JP2007084524A
3
JP2007308427A
4
JP2008214479A
3
JP2009263324A
5
JP2011529977A
3
JP2012500104A
108
JP3016599B2
3
JP4550838B2
3
JP4728230B2
5
JP4820369B2
7
JPH01174526A
3
JPH01319528A
3
JPH0211551A
3
JPH02170862A
3
JPH02188556A
3
JPH0219368A
3
JPH02232224A
3
JPH02240138A
3
JPH0269448A
3
JPH03112946A
5
JPH03127762A
5
JPH03177419A
3
JPH04108824A
3
JPH04154860A
3
JPH0496924A
3
JPH05156007A
3
JPH05170902A
4
JPH05174621A
3
JPH05221937A
3
JPH0551450A
3
JPH06219999A
3
JPH06228303A
3
US3079435 A
3

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 Mon Mar 31 18:38:47 GMT 2025
Edited
by admin
on Mon Mar 31 18:38:47 GMT 2025
Record UNII
R7P8FRP05V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-AMINOPHENOL
HSDB   USP-RS  
Preferred Name English
p-Aminophenol
INCI   MI  
INCI  
Official Name English
4-AMINOPHENOL [USP IMPURITY]
Common 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
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 Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
NSC
1545
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
PUBCHEM
403
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
DAILYMED
R7P8FRP05V
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
DRUG BANK
DB14144
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
EVMPD
SUB169709
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
RS_ITEM_NUM
1021204
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
MERCK INDEX
m1728
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY Merck Index
MESH
C026729
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
RXCUI
1435279
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY RxNorm
FDA UNII
R7P8FRP05V
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
EPA CompTox
DTXSID3024499
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
HSDB
2640
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
WIKIPEDIA
4-AMINOPHENOL
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
CHEBI
17602
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
CAS
123-30-8
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
SMS_ID
100000159523
Created by admin on Mon Mar 31 18:38:47 GMT 2025 , Edited by admin on Mon Mar 31 18:38:47 GMT 2025
PRIMARY
Related Record Type Details
Structure of P-AMINOPHENOL SULFATE
SALT/SOLVATE -> PARENT
Structure of P-AMINOPHENOL HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of Sodium 4-aminophenolate
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
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