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Record Information
Version1.0
Creation Date2009-03-06 18:58:28 UTC
Update Date2016-11-09 01:08:12 UTC
Accession NumberCHEM000251
Identification
Common NameArsanilic acid
ClassSmall Molecule
DescriptionArsanilic acid is an organoarsenic compound derived from orthoarsenic acid. It was once used as a human drug, but is now only found in veterinary medicine, where its use is controversial. (11)
Contaminant Sources
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Aromatic Hydrocarbon
  • Arsenic Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organometallic
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
(p-Aminophenyl)arsonic acidChEBI
4-Aminobenzenearsonic acidChEBI
4-AMINOPHENYLARSONIC ACIDChEBI
4-AminophenylarsonsaeureChEBI
4-Arsanilic acidChEBI
ArsanilsaeureChEBI
Atoxylic acidChEBI
p-Arsanilic acidChEBI
(p-Aminophenyl)arsonateGenerator
4-AminobenzenearsonateGenerator
4-AMINOPHENYLARSONateGenerator
4-ArsanilateGenerator
AtoxylateGenerator
p-ArsanilateGenerator
ArsanilateGenerator
p-Aminophenylarsonic acidMeSH
Sodium arsanilateMeSH
Sodium arsenilateMeSH
Acid, 4-aminobenzenearsonicMeSH
Arsanilate, sodiumMeSH
Arsenilate, sodiumMeSH
4 Aminobenzenearsonic acidMeSH
Acid, arsanilicMeSH
p Aminophenylarsonic acidMeSH
Acid, p-aminophenylarsonicMeSH
AtoxylMeSH
Chemical FormulaC6H8AsNO3
Average Molecular Mass217.054 g/mol
Monoisotopic Mass216.972 g/mol
CAS Registry Number98-50-0
IUPAC Name(4-aminophenyl)arsonic acid
Traditional Namearsanilic acid
SMILESNC1=CC=C(C=C1)[As](O)(O)=O
InChI IdentifierInChI=1S/C6H8AsNO3/c8-6-3-1-5(2-4-6)7(9,10)11/h1-4H,8H2,(H2,9,10,11)
InChI KeyXKNKHVGWJDPIRJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentAniline and substituted anilines
Alternative Parents
Substituents
  • Aniline or substituted anilines
  • Pentaorganoarsane
  • Oxygen-containing organoarsenic compound
  • Organic metalloid salt
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Primary amine
  • Organonitrogen compound
  • Organoarsenic compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point232°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility11 g/LALOGPS
logP-0.42ALOGPS
logP-0.17ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.95ChemAxon
pKa (Strongest Basic)2.73ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.75 m³·mol⁻¹ChemAxon
Polarizability16.29 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-30f0559de8fcde9d1269View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0790000000-3c61577b3f67c3581d93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-4910000000-0087634d59ed9ee64e5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-2960000000-85e6e166870124b6f622View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014l-6090000000-c2bc171b4453965b1702View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-009f-9700000000-36a1a6665c8d0889bc74View in MoNA
Toxicity Profile
Route of ExposureOral (6) ; inhalation (6); dermal (6)
Mechanism of ToxicityArsenic and its metabolites disrupt ATP production through several mechanisms. At the level of the citric acid cycle, arsenic inhibits pyruvate dehydrogenase and by competing with phosphate it uncouples oxidative phosphorylation, thus inhibiting energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is also increased, which might form reactive oxygen species and oxidative stress. Arsenic's carcinogenicity is influenced by the arsenical binding of tubulin, which results in aneuploidy, polyploidy and mitotic arrests. The binding of other arsenic protein targets may also cause altered DNA repair enzyme activity, altered DNA methylation patterns and cell proliferation. (3, 2)
MetabolismArsenic is absorbed mainly by inhalation or ingestion, as to a lesser extent, dermal exposure. It is then distributed throughout the body, where it is reduced into arsenite if necessary, then methylated into monomethylarsenic (MMA) and dimethylarsenic acid (DMA) by arsenite methyltransferase. Arsenic and its metabolites are primarily excreted in the urine. Arsenic is known to induce the metal-binding protein metallothionein, which decreases the toxic effects of arsenic and other metals by binding them and making them biologically inactive, as well as acting as an antioxidant. (7)
Toxicity ValuesLD50: 248 mg/kg (Intraperitoneal, Mouse) (4) LD50: 100 mg/kg (Intravenous, Mouse) (4)
Lethal Dose130 mg for an adult human. (5)
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (10)
Uses/SourcesArsanilic acid is used to treate dysentery in swine. (11)
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (9) Chronic Oral: 0.0003 mg/kg/day (9) Chronic Inhalation: 0.01 mg/m3 (9)
Health EffectsArsenic poisoning can lead to death from multi-system organ failure, probably from necrotic cell death, not apoptosis. Arsenic is also a known carcinogen, especially in skin, liver, bladder and lung cancers. (3, 7)
SymptomsExposure to lower levels of arsenic can cause nausea and vomiting, decreased production of red and white blood cells, abnormal heart rhythm, damage to blood vessels, and a sensation of “pins and needles” in hands and feet. Breathing high levels of inorganic arsenic can give you a sore throat or irritated lungs. Arsenic also affects the brain, causing neurological disturbances such as headaches, confusion, and drowsiness. (1)
TreatmentArsenic poisoning can be treated by chelation therapy, using chelating agents such as dimercaprol, EDTA or DMSA. Charcoal tablets may also be used for less severe cases. In addition, maintaining a diet high in sulfur helps eliminate arsenic from the body. (7)
Concentrations
Not Available
DrugBank IDDB03006
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkArsanilic acid
Chemspider IDNot Available
ChEBI ID49477
PubChem Compound ID7389
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available