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
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
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL5101 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10692486 |
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Target ID: CHEMBL5101 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10692486 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Isolation and characterization of a pseudomonas strain that degrades 4-acetamidophenol and 4-aminophenol. | 2001 |
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Contact anaphylaxis due to para-aminophenol and para-methylaminophenol in hair dye. | 2001 Dec |
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Determination of 4-aminophenol impurities in selected pharmaceutical preparations by HPLC method with amperometric detection. | 2001 Sep-Oct |
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Renal PGE2 production in the human and rat following phenacetin, acetaminophen and p-aminophenol. | 2002 |
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Synthesis and beta 1-, beta 2-adrenergic receptor binding studies of 4-acylamino-substituted phenoxypropanolamine and 5-acylamino-substituted naphthyloxypropanolamine derivatives. | 2002 |
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An in-vitro study of the effects of various disinfectants on prosthetic and surface materials. | 2002 Apr |
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The spectrum of allergic (cross-)sensitivity in clinical patch testing with 'para amino' compounds. | 2002 Apr |
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A glucose dehydrogenase biosensor as an additional signal amplification step in an enzyme-flow immunoassay. | 2002 Aug |
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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 |
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Liver regeneration is an angiogenesis- associated phenomenon. | 2002 Dec |
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GDH biosensor based off-line capillary immunoassay for alkylphenols and their ethoxylates. | 2002 Dec |
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A physiochemical mechanism of hemozoin (beta-hematin) synthesis by malaria parasite. | 2002 Jan 11 |
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Cytokinin oxidase/cytokinin dehydrogenase assay: optimized procedures and applications. | 2002 Jul 1 |
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NMR and Bayesian regularized neural network regression for impurity determination of 4-aminophenol. | 2002 Jul 1 |
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Determination of the rate constants and activation energy of acetaminophen hydrolysis by capillary electrophoresis. | 2002 Jul 31 |
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[Research into simultaneous spectrophotometric determination of components in cough syrup by principal component regression method]. | 2002 Jun |
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Determination of 4-aminophenol using the quartz crystal microbalance sensor. | 2002 Mar |
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Simultaneous LC determination of paracetamol and related compounds in pharmaceutical formulations using a carbon-based column. | 2002 Mar 1 |
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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 |
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Cross-sensitization to haptens: formation of common haptenic metabolites, T cell recognition of cryptic peptides, and true T cell cross-reactivity. | 2002 May |
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Anti-tumour activity and toxicity of the new prodrug 9-aminocamptothecin glucuronide (9ACG) in mice. | 2002 May 20 |
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Design and synthesis of aminophenol-based factor Xa inhibitors. | 2002 May 6 |
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Deviceless decoupled electrochemical detection of catecholamines in capillary electrophoresis using gold microband array electrodes. | 2002 Nov |
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Biological activity of p-methylaminophenol, an essential structural component of N-(4-hydroxyphenyl)retinamide, fenretinide. | 2002 Nov |
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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 |
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Novel electrochemical immunosensors for seafood toxin analysis. | 2002 Sep |
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Immobilizing a single pybox ligand onto a library of solid supports. | 2003 |
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The use of thermal lensing for the determination of pyrogens. | 2003 Apr |
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Generation of ligand conformations in continuum solvent consistent with protein active site topology: application to thrombin. | 2003 Apr 10 |
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Metalloantimalarials: targeting of P. falciparum strains with novel iron(III) and gallium(III) complexes of an amine phenol ligand. | 2003 Apr 7 |
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Evolution of catabolic pathways for synthetic compounds: bacterial pathways for degradation of 2,4-dinitrotoluene and nitrobenzene. | 2003 Aug |
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Synthesis and activity of novel benzoxazole derivatives of mannopeptimycin glycopeptide antibiotics. | 2003 Aug 4 |
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A capillary-based amperometric flow immunoassay for 2,4,6-trichlorophenol. | 2003 Jan |
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Continuous biotransformation and removal of nitrophenols under denitrifying conditions. | 2003 Jul |
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Validation of a method for quantification of ketobemidone in human plasma with liquid chromatography-tandem mass spectrometry. | 2003 Jun 15 |
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A potential biomarker of kidney damage identified by proteomics: preliminary findings. | 2003 May-Aug |
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Enzyme-amplified electrochemical detection of DNA using electrocatalysis of ferrocenyl-tethered dendrimer. | 2003 Nov 1 |
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First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry. | 2003 Nov 5 |
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A new dynamic electrochemical transduction mechanism for interdigitated array microelectrodes. | 2004 Dec |
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Degradation of 4-nitrophenol by the lignin-degrading basidiomycete Phanerochaete chrysosporium. | 2004 Dec |
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Express detection of nonylphenol in water samples by fluorescence polarization immunoassay. | 2004 Feb |
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[Kinetics and mechanism of aniline oxidation with chlorine dioxide in water]. | 2004 Jan |
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Electric chips for rapid detection and quantification of nucleic acids. | 2004 Jan 15 |
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Hair dye contact allergy: quantitative exposure assessment of selected products and clinical cases. | 2004 Jun |
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Toxic effects of aminophenols on aquatic life using the zebrafish embryo test and the comet assay. | 2004 Oct |
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Microchip capillary electrophoresis with a boron-doped diamond electrochemical detector for analysis of aromatic amines. | 2004 Sep |
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Pharmacophore based synthesis of 3-chloroquinoxaline-2-carboxamides as serotonin3 (5-HT3) receptor antagonist. | 2004 Sep |
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Automated spectrophotometric assay for urine p-aminophenol by an oxidative coupling reaction. | 2004 Summer |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21771276
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
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on
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Record UNII |
R7P8FRP05V
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Validated (UNII)
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1545
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403
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M1728
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C026729
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4-AMINOPHENOL
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE |
May be substrate for formation of AM-404
MINOR
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (GC)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |