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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 NumberCHEM000261
Identification
Common Name4,4-Arsenobis(2-aminophenol) dihydrochloride
ClassSmall Molecule
Description4,4-arsenobis(2-aminophenol) dihydrochloride is an arsenical drug believed to be the first modern chemotherapeutic agent. It was used to treat syphilis and trypanosomiasis.
Contaminant Sources
  • IARC Carcinogens Group 3
  • T3DB toxins
Contaminant Type
  • Amine
  • Aromatic Hydrocarbon
  • Arsenic Compound
  • Drug
  • Organic Compound
  • Organometallic
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
3,3'-Diamino-4,4'-dihydroxyarsenobenzene dihydrochlorideChEBI
4,4'-(1,2-Diarsenediyl)bis(2-aminophenol) dihydrochlorideChEBI
4,4'-(Diarsene-1,2-diyl)bis(2-aminophenol) dihydrochlorideChEBI
4,4'-Arsenobis(2-aminophenol) dihydrochlorideChEBI
6,6'-Dihydroxy-3,3'-diarsene-1,2-diyldianilinium dichlorideChEBI
Arsenphenolamine hydrochlorideChEBI
Ehrlich 606ChEBI
SalvarsanChEBI
ArsphenamineKegg
Arsenobenzol, sodiumMeSH
Sodium arsenobenzolMeSH
ArsenobenzolMeSH
Chemical FormulaC12H14As2Cl2N2O2
Average Molecular Mass439.001 g/mol
Monoisotopic Mass437.886 g/mol
CAS Registry Number139-93-5
IUPAC Name2-amino-4-[2-(3-amino-4-hydroxyphenyl)diarsen-1-yl]phenol dihydrochloride
Traditional Name2-amino-4-[2-(3-amino-4-hydroxyphenyl)diarsen-1-yl]phenol dihydrochloride
SMILESCl.Cl.NC1=CC(=CC=C1O)[As]=[As]C1=CC=C(O)C(N)=C1
InChI IdentifierInChI=1S/C12H12As2N2O2.2ClH/c15-9-5-7(1-3-11(9)17)13-14-8-2-4-12(18)10(16)6-8;;/h1-6,17-18H,15-16H2;2*1H
InChI KeyVLAXZGHHBIJLAD-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
  • Aminophenol
  • O-aminophenol
  • Aniline or substituted anilines
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Oxygen-containing organoarsenic compound
  • Organic metalloid salt
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Hydrochloride
  • Organic salt
  • Primary amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organoarsenic compound
  • Organic nitrogen 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 Point190°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
logP1.92ChemAxon
pKa (Strongest Acidic)10.08ChemAxon
pKa (Strongest Basic)4.35ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area92.5 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.31 m³·mol⁻¹ChemAxon
Polarizability27.23 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-000i-0000900000-c0a907d8d95426c9aa30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-c0a907d8d95426c9aa30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0000900000-c0a907d8d95426c9aa30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-7a31815ef2245d0fd6f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-7a31815ef2245d0fd6f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0000900000-7a31815ef2245d0fd6f8View 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. (4)
Uses/Sources4,4-arsenobis(2-aminophenol) dihydrochloride was used to treat syphilis and trypanosomiasis.
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (7) Chronic Oral: 0.0003 mg/kg/day (7) Chronic Inhalation: 0.01 mg/m3 (7)
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 IDNot Available
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 LinkNot Available
Chemspider IDNot Available
ChEBI ID9016
PubChem Compound ID8774
Kegg Compound IDC11744
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available