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Record Information
Version1.0
Creation Date2009-03-06 18:58:30 UTC
Update Date2016-11-09 01:08:12 UTC
Accession NumberCHEM000264
Identification
Common NameNitarsone
ClassSmall Molecule
DescriptionAntiprotozoal, antihistomonad; mainly used for poultry Nitarsone belongs to the family of Nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
Contaminant Sources
  • FooDB Chemicals
  • IARC Carcinogens Group 3
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Arsenic Compound
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Organometallic
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
(p-Nitrophenyl)arsonic acidChEBI
4-Nitrobenzenearsonic acidChEBI
4-Nitrophenylarsonic acidChEBI
4-O2c6h4AsO3h2ChEBI
HistostatChEBI
NitarsonChEBI
NitarsonumChEBI
p-Nitrobenzenearsonic acidChEBI
p-Nitrophenylarsonic acidChEBI
(p-Nitrophenyl)arsonateGenerator
4-NitrobenzenearsonateGenerator
4-NitrophenylarsonateGenerator
p-NitrobenzenearsonateGenerator
p-NitrophenylarsonateGenerator
(4-Nitrophenyl)-arsonic acidHMDB
4-(Hydroxy(oxido)amino)phenylarsonic acidHMDB
Arsonic acid, 4-nitrophenylHMDB
C6H6AsNO5HMDB
Hep-a-statHMDB
Histostat 50HMDB
Histostat-50HMDB
Nitarsone(usan)HMDB
Nitarsone, inn, usanHMDB
NSC 5085HMDB
p-Nitro-benzenearsonic acidHMDB
p-Nitrobenzenearsonic acid, 8ciHMDB
Nitarsone, monosodium saltHMDB
Nitarsone, disodium saltHMDB
Chemical FormulaC6H6AsNO5
Average Molecular Mass247.037 g/mol
Monoisotopic Mass246.946 g/mol
CAS Registry Number98-72-6
IUPAC Name(4-nitrophenyl)arsonic acid
Traditional Namehistostat
SMILESO[As](O)(=O)C1=CC=C(C=C1)N(=O)=O
InChI IdentifierInChI=1S/C6H6AsNO5/c9-7(10,11)5-1-3-6(4-2-5)8(12)13/h1-4H,(H2,9,10,11)
InChI KeyFUUFQLXAIUOWML-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Nitroaromatic compound
  • Pentaorganoarsane
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Oxygen-containing organoarsenic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic metalloid salt
  • Organic 1,3-dipolar compound
  • Organic nitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organoarsenic compound
  • Organopnictogen compound
  • Organic oxygen compound
  • 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
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceNo data.
Experimental Properties
PropertyValue
Melting Point298 - 300°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.83 g/LALOGPS
logP0.06ALOGPS
logP0.88ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area103.35 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.37 m³·mol⁻¹ChemAxon
Polarizability17.23 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-004i-2890000000-a3acf3293eae7a0684b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-62891226aa9ca258ede2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0090000000-2d936ca40f0bface1726View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-1970000000-dfc529b0f93c6dcc8d1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-a16175bbc62ffed663b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-0cadf4e759362c6d473eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1930000000-16f839acf98e7ba63149View in MoNA
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5); dermal (5)
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, 1)
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. (6)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (7)
Uses/Sources(4-nitrophenyl)arsonic acid is found in animal feed.
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (8) Chronic Oral: 0.0003 mg/kg/day (8) Chronic Inhalation: 0.01 mg/m3 (8)
Health EffectsHypovolemia from capillary leakage (third-spacing of fluids) is a common, serious, early effect. Muscle cramps, facial edema, bronchitis, dyspnea, chest pain, dehydration, intense thirst, and fluid-electrolyte disturbances are also common following significant exposures. A garlic-like odor of the breath and feces may also occur. After absorption, arsenic may cause multi-organ failure by inhibiting sulfhydryl-containing enzymes. Encephalopathy, with headache, lethargy, mental confusion, hallucinations, emotional lability, memory loss and delirium may occur; seizures, stupor, convulsions, coma, and death may follow within 24 hours of a severe acute exposure. Dysrhythmias (particularly QTc prolongation and torsade de pointes), cardiomyopathy, ARDS, hepatitis, rhabdomyolysis, hemolysis, and renal failure may develop over several days. The sequence of chronic poisoning involves hyperpigmentation, and eczematoid and allergic dermatitis. muscle fasciculations; gross tremors; ataxia; incoordination; and mental confusion. Muscular weakness, limb tenderness and difficulty walking may follow. The final phase consists of peripheral sensory neuropathy of the hands and feet. That may be associated with a motor neuropathy as well (2).
SymptomsInitial signs and symptoms of arsenic ingestion include burning lips, throat constriction and dysphagia, followed by excruciating abdominal pain, hemorrhagic gastritis, gastroenteritis, severe nausea, projectile voting, profuse "rice water-like" diarrhea, with hypovolemia that may result in hypotension and an irregular pulse. The sequence of chronic poisoning involves weakness, anorexia, hepatomegaly, jaundice, and gastrointestinal complaints, followed by conjunctivitis, irritation of the throat and respiratory tract. ther effects of chronic exposure include conjunctivitis with irritation and lacrimation; hair, skin and nail changes; hyperkeratosis of feet and hands; and melanosis, with pigment spots in corneal and conjunctival epithelium. Peripheral nervous system symptoms may include numbness, burning, and tingling of the hands and feet; pain; paresthesias; tenderness (2).
TreatmentAggressive decontamination with gastric lavage is recommended if the patient has consumed a potentially life-threatening dose and if the patient is not vomiting (2).
Concentrations
Not Available
DrugBank IDDB11437
HMDB IDHMDB0031822
FooDB IDFDB008500
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNitarsone
Chemspider ID60190
ChEBI ID62629
PubChem Compound ID66826
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16550417
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21388897
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=4674928
4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.