You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Database of hazardous chemicals.
Record Information
Version1.0
Creation Date2009-06-19 21:58:35 UTC
Update Date2016-11-09 01:08:27 UTC
Accession NumberCHEM001130
Identification
Common NameLewisite
ClassSmall Molecule
DescriptionLewisite is a organoarsenic compound which belongs to the group of chemical warfare agents known as blister agents or vesicants. Due to its toxicity, it is nowadays considered obsolete. Arsenic is a chemical element that has the symbol As and atomic number 33. It is a poisonous metalloid that has many allotropic forms: yellow (molecular non-metallic) and several black and grey forms (metalloids) are a few that are seen. Three metalloidal forms of arsenic with different crystal structures are found free in nature (the minerals arsenopyrite and the much rarer arsenolamprite and pararsenolamprite), but it is more commonly found as a compound with other elements. (3, 10)
Contaminant Sources
  • Clean Air Act Chemicals
  • IARC Carcinogens Group 3
  • T3DB toxins
Contaminant Type
  • Arsenic Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Organometallic
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
Dichloro(2-chlorovinyl)arsineMeSH
Lewisite, (Z)-isomerMeSH
Chemical FormulaC2H2AsCl3
Average Molecular Mass207.318 g/mol
Monoisotopic Mass205.844 g/mol
CAS Registry Number541-25-3
IUPAC Namedichloro[(E)-2-chloroethenyl]arsane
Traditional Namelewisite
SMILESCl\C=C\[As](Cl)Cl
InChI IdentifierInChI=1S/C2H2AsCl3/c4-2-1-3(5)6/h1-2H/b2-1+
InChI KeyGIKLTQKNOXNBNY-OWOJBTEDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dihaloarsines. These are organoarsenic compounds with the general formula R[As](X)X, where R = Organyl group, and X = halogen atom.
KingdomOrganic compounds
Super ClassOrganometallic compounds
ClassOrganometalloid compounds
Sub ClassOrganoarsenic compounds
Direct ParentDihaloarsines
Alternative Parents
Substituents
  • Dihaloarsine
  • Trivalent organic arsenic compound
  • Organic metalloid salt
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organochloride
  • Organohalogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateGas
AppearanceColorless gas.
Experimental Properties
PropertyValue
Melting Point0.1°C
Boiling Point190°C
Solubility0.5 mg/mL [GOLDMAN,M & DACRE,JC (1989)]
Predicted Properties
PropertyValueSource
Water Solubility2.88 g/LALOGPS
logP2.49ALOGPS
logP2.5ChemAxon
logS-1.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.56 m³·mol⁻¹ChemAxon
Polarizability13.41 ųChemAxon
Number of Rings0ChemAxon
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, Positivesplash10-0a4i-1090000000-bc69ceb35a1b531333b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0390000000-d89ca9d73a220190a6f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-9500000000-f8321d06c32eb3899437View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-2bde254b481305d69798View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-1000-6790000000-9b5f0b31760f947c2fb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3490000000-c6fddd151089b2308e46View in MoNA
MSMass Spectrum (Electron Ionization)splash10-06rt-1930000000-4ac317d46c530a07be84View 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 carginogenicity 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. (2, 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 ValuesLD50: 50 mg/kg (Oral, Rat) (4) LD50: 0.5 mg/kg (Intravenous, Rat) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (9)
Uses/SourcesLewisite belongs to the group of chemical warfare agents known as blister agents or vesicants. Due to its toxicity, it is nowadays considered obsolete. (10)
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 EffectsArsenic poisoning can lead to death from multi-system organ failure, probably from necrotic cell death, not apoptosis. Arsenic is also a known carcinogen, esepcially in skin, liver, bladder and lung cancers. (2, 6)
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
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. (6)
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 LinkLewisite
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5372798
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available