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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
A new dynamic electrochemical transduction mechanism for interdigitated array microelectrodes.
2004-12
Degradation of 4-nitrophenol by the lignin-degrading basidiomycete Phanerochaete chrysosporium.
2004-12
Reactions of arylamine and aminophenol derivatives, and riboflavin with organic radicals.
2004-11
Toxic effects of aminophenols on aquatic life using the zebrafish embryo test and the comet assay.
2004-10
Microchip capillary electrophoresis with a boron-doped diamond electrochemical detector for analysis of aromatic amines.
2004-09
Pharmacophore based synthesis of 3-chloroquinoxaline-2-carboxamides as serotonin3 (5-HT3) receptor antagonist.
2004-09
Poly(dimethylsiloxane) microchip capillary electrophoresis with electrochemical detection for rapid measurement of acetaminophen and its hydrolysate.
2004-08
The measurement of alkaline phosphatase at nanomolar concentration within 70 s using a disposable microelectrochemical transistor.
2004-08
The demonstration of an enhanced microelectrochemical transistor for measurements in neutral solution at low analyte concentration.
2004-08
Spectrophotometric determination of paracetamol with microwave assisted alkaline hydrolysis.
2004-07
Scanning electrochemical microscopy of quinoprotein glucose dehydrogenase.
2004-06-01
Hair dye contact allergy: quantitative exposure assessment of selected products and clinical cases.
2004-06
Bead-based immunoassays with microelectrode detection.
2004-06
Bead-based electrochemical immunoassay for bacteriophage MS2.
2004-05-15
Microbead-based electrochemical immunoassay with interdigitated array electrodes.
2004-05-15
Synthesis and biological activity of novel retinamide and retinoate derivatives.
2004-05
Hapten-directed targeting to single-chain antibody receptors.
2004-05
Toxicity and human health risk of hair dyes.
2004-04
Flow injection determination of p-aminophenol at trace level using inhibited luminol-dimethylsulfoxide-NaOH-EDTA chemiluminescence.
2004-03-25
Electrical detection of viral DNA using ultramicroelectrode arrays.
2004-02-01
Express detection of nonylphenol in water samples by fluorescence polarization immunoassay.
2004-02
Electric chips for rapid detection and quantification of nucleic acids.
2004-01-15
[Kinetics and mechanism of aniline oxidation with chlorine dioxide in water].
2004-01
Effect of unlabeled helper probes on detection of an RNA target by bead-based sandwich hybridization.
2004-01
Automated spectrophotometric assay for urine p-aminophenol by an oxidative coupling reaction.
2004
Kinetics of aniline oxidation with chlorine dioxide.
2004
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.
2003-12-25
Oxidation-reduction potential as a control variable for the anaerobic stage during anaerobic-aerobic p-nitrophenol degradation.
2003-12-06
First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry.
2003-11-05
Enzyme-amplified electrochemical detection of DNA using electrocatalysis of ferrocenyl-tethered dendrimer.
2003-11-01
A potential biomarker of kidney damage identified by proteomics: preliminary findings.
2003-08-29
Determination of 4-aminophenol impurities in multicomponent analgesic preparations by HPLC with amperometric detection.
2003-08-08
Synthesis and activity of novel benzoxazole derivatives of mannopeptimycin glycopeptide antibiotics.
2003-08-04
Immobilized enzyme-linked DNA-hybridization assay with electrochemical detection for Cryptosporidium parvum hsp70 mRNA.
2003-08-01
Evolution of catabolic pathways for synthetic compounds: bacterial pathways for degradation of 2,4-dinitrotoluene and nitrobenzene.
2003-08
Enhancement of antioxidant activity of p-alkylaminophenols by alkyl chain elongation.
2003-07-31
Continuous biotransformation and removal of nitrophenols under denitrifying conditions.
2003-07
Validation of a method for quantification of ketobemidone in human plasma with liquid chromatography-tandem mass spectrometry.
2003-06-15
Unbiased spectrophotometric method for estimating phenol or o-cresol in unknown water samples.
2003-06
Generation of ligand conformations in continuum solvent consistent with protein active site topology: application to thrombin.
2003-04-10
Metalloantimalarials: targeting of P. falciparum strains with novel iron(III) and gallium(III) complexes of an amine phenol ligand.
2003-04-07
Sorption and diffusion of phenols onto well-defined ordered nanoporous monolithic silicas.
2003-04-01
The use of thermal lensing for the determination of pyrogens.
2003-04
Reversible and irreversible inhibitory activity of succinic and maleic acid derivatives on acetylcholinesterase.
2003-04
Dlf complexes with uniform coordination geometry: structural and magnetic properties of an LnNi2 core supported by a heptadentate amine phenol ligand.
2003-03-10
Synthesis of 11C-amides using [11C]carbon monoxide and in situ activated amines by palladium-mediated carboxaminations.
2003-02-07
Immobilizing a single pybox ligand onto a library of solid supports.
2003
[Research into simultaneous spectrophotometric determination of components in cough syrup by principal component regression method].
2002-06
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
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
ACTIVE MOIETY
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