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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

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

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
The degradation of paracetamol (4-hydroxyacetanilide) and other substituted acetanilides by a Penicillium species.
1975
Isolation and characterization of a pseudomonas strain that degrades 4-acetamidophenol and 4-aminophenol.
2001
p-Aminophenol-induced liver toxicity: tentative evidence of a role for acetaminophen.
2001
Metabolism of (R)- and (S)-3-(phenylamino)propane-1,2-diol in C57BL/6- and A/J-strain mice. Identification of new metabolites with potential toxicological significance to the toxic oil syndrome.
2001 Aug
Contact anaphylaxis due to para-aminophenol and para-methylaminophenol in hair dye.
2001 Dec
Potentiation of antitumor immunity by antibody-directed enzyme prodrug therapy.
2001 Dec 15
Small volume bead assay for ovalbumin with electrochemical detection.
2001 Mar
Quantitative analysis of analgoantipyretics in dosage form using planar chromatography.
2001 Mar
Chloroform-soluble schiff-base Zn(II) or Cd(II) complexes from a dynamic combinatorial library.
2001 Mar 26
Determination of 5-aminosalicylic acid related impurities by micellar electrokinetic chromatography with an ion-pair reagent.
2001 May 4
Determination of salicylate in blood serum by flow injection with immobilized salicylate hydroxylase.
2001 Sep-Oct
Renal PGE2 production in the human and rat following phenacetin, acetaminophen and p-aminophenol.
2002
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
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
Biological activity of p-methylaminophenol, an essential structural component of N-(4-hydroxyphenyl)retinamide, fenretinide.
2002 Nov
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
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
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
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
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
The measurement of alkaline phosphatase at nanomolar concentration within 70 s using a disposable microelectrochemical transistor.
2004 Aug
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
Scanning electrochemical microscopy of quinoprotein glucose dehydrogenase.
2004 Jun 1
Microbead-based electrochemical immunoassay with interdigitated array electrodes.
2004 May 15
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 Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Fri Dec 15 16:58:58 GMT 2023
Edited
by admin
on Fri Dec 15 16:58:58 GMT 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 Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
NSC
1545
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
PUBCHEM
403
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
DAILYMED
R7P8FRP05V
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
DRUG BANK
DB14144
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
EVMPD
SUB169709
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
RS_ITEM_NUM
1021204
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
MERCK INDEX
m1728
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY Merck Index
MESH
C026729
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
RXCUI
1435279
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY RxNorm
FDA UNII
R7P8FRP05V
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID3024499
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
HSDB
2640
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
WIKIPEDIA
4-AMINOPHENOL
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
CHEBI
17602
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
CAS
123-30-8
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
SMS_ID
100000159523
Created by admin on Fri Dec 15 16:58:58 GMT 2023 , Edited by admin on Fri Dec 15 16:58:58 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE ACTIVE
May be substrate for formation of AM-404
MINOR
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY