Ethyldichloroarsine (CHEM001129)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (70)XML
Record Information
Version1.0
Creation Date2009-06-19 21:58:35 UTC
Update Date2026-08-22 09:47:19 UTC
Accession NumberCHEM001129
Identification
Common NameEthyldichloroarsine
ClassSmall Molecule
DescriptionEthyldichloroarsine is an exogenous organoarsenic compound with the formula C2H5AsCl2 and an average molecular weight of 174.89 g/mol. It exists as a gas at room temperature. Ethyldichloroarsine belongs to the organoarsenic compounds, a subclass of organometalloid compounds within the organic compounds. The compound interacts with 33 recorded protein targets. Arsenic binds to hemoglobin (HBA1, HBB), haptoglobin, and the glucocorticoid receptor (NR3C1). It also binds to actin in several forms, including alpha skeletal muscle (ACTA1), aortic smooth muscle (ACTA2), cytoplasmic 1 (ACTB), and cytoplasmic 2 (ACTG1). In humans, it causes endocrine disruption by binding to and inhibiting the estrogen receptor (ESR1, ESR2). Furthermore, arsenic binds glutathione reductase (GSR), resulting in the inhibition of essential biochemical reactions, alteration of cellular redox status, and eventual cytotoxicity. Arsenic disrupts ATP production through several mechanisms. Within the citric acid cycle, it inhibits pyruvate dehydrogenase—specifically the PDHA1, PDHA2, and PDHB subunits, as well as the dihydrolipoyllysine-residue acetyltransferase component (DLAT). By competing with phosphate, it uncouples oxidative phosphorylation, which inhibits mitochondrial respiration, ATP synthesis, and the energy-linked reduction of NAD+. This process also increases hydrogen peroxide production, which may lead to oxidative stress and the formation of reactive oxygen species. Additionally, arsenic binding of XPA is believed to induce carcinogenesis by affecting DNA repair.
Contaminant Sources
  • IARC Carcinogens Group 3
  • T3DB toxins
Contaminant Type
  • Arsenic Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Organometallic
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC2H5AsCl2
Average Molecular Mass174.889 g/mol
Monoisotopic Mass173.898 g/mol
CAS Registry Number598-14-1
IUPAC Namedichloro(ethyl)arsane
Traditional Nameethyldichloroarsine
SMILESCC[As](Cl)Cl
InChI IdentifierInChI=1S/C2H5AsCl2/c1-2-3(4)5/h2H2,1H3
InChI KeyLQSFEOMOHFPNEB-UHFFFAOYSA-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
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
StateGas
AppearanceColorless gas.
Experimental Properties
PropertyValue
Melting Point-65°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility12.5 g/LALOGPS
logP2.05ALOGPS
logP1.75ChemAxon
logS-1.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.88 m³·mol⁻¹ChemAxon
Polarizability12.03 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-41ec2b1c34bc4bbc5a97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-6346a8fd5dfc0ce7bad9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-7900000000-c2038aa5dfca7879d3daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-c70cc8084c52b401e4a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-0b409c2273896cd9c772Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-1900000000-22e13cdfe4d254893871Spectrum
Toxicity Profile
Route of ExposureOral (2) ; inhalation (2) ; dermal (2)
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. (8, 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. (3)
Toxicity ValuesLC50: 1555 mg/m3 over 10 minutes (Inhalation, Mouse) (10)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (6)
Uses/SourcesEthyldichloroarsine belongs to the group of chemical warfare agents known as blister agents or vesicants. Due to its toxicity, it is nowadays considered obsolete. (7)
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (5) Chronic Oral: 0.0003 mg/kg/day (5) Chronic Inhalation: 0.01 mg/m3 (5)
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. (8, 3)
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. (3)
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 LinkEthyldichloroarsine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID11711
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available