<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">1315</id>
  <title>T3D1311</title>
  <common-name>Methyldichloroarsine</common-name>
  <description>Methyldichloroarsine is an exogenous organoarsenic compound with the formula CH3AsCl2 and an average molecular weight of 160.86 g/mol. It exists as a gas at room temperature. Methyldichloroarsine belongs to the organoarsenic compounds, a subclass of organometalloid compounds within the organic compounds.

The compound interacts with numerous 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). Interaction with the estrogen receptors (ESR1, ESR2) causes endocrine disruption in humans through binding and inhibition. Additionally, arsenic binds to glutathione reductase, mitochondrial (GSR), which inhibits essential biochemical reactions, alters cellular redox status, and leads to eventual cytotoxicity.

Methyldichloroarsine disrupts ATP production through several mechanisms. Within the citric acid cycle, arsenic inhibits pyruvate dehydrogenase, involving the mitochondrial components PDHA1, PDHA2, PDHB, and DLAT. By competing with phosphate, it uncouples oxidative phosphorylation, thereby inhibiting mitochondrial respiration, ATP synthesis, and the energy-linked reduction of NAD+. This process is accompanied by increased hydrogen peroxide production, which may lead to oxidative stress and the formation of reactive oxygen species. Furthermore, arsenic binding of XPA is believed to induce carcinogenesis by affecting DNA repair.</description>
  <cas>593-89-5</cas>
  <pubchem-id>61142</pubchem-id>
  <chemical-formula>CH3AsCl2</chemical-formula>
  <weight>159.882780</weight>
  <appearance>Colorless gas.</appearance>
  <melting-point>-55°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral (L2) ; inhalation (L2) ; dermal (L2)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Arsenic 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. (T1, A17)</mechanism-of-toxicity>
  <metabolism>Arsenic 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. (L20)</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use-source>Methyldichloroarsine belongs to the group of chemical warfare agents known as blister agents or vesicants. Due to its toxicity, it is nowadays considered obsolete. (L366)</use-source>
  <min-risk-level>Acute Oral: 0.005 mg/kg/day (L134) 
Chronic Oral: 0.0003 mg/kg/day (L134) 
Chronic Inhalation: 0.01 mg/m3 (L134)</min-risk-level>
  <health-effects>Arsenic 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. (T1, L20)</health-effects>
  <symptoms>Exposure 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 </symptoms>
  <treatment>Arsenic 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. (L20)</treatment>
  <created-at type="dateTime">2009-06-19T21:58:35Z</created-at>
  <updated-at type="dateTime">2026-08-26T00:14:05Z</updated-at>
  <interacting-proteins>Metallothionein-2 (P02795) Metallothionein-1G (P13640) Metallothionein-1H (P80294) Metallothionein-3 (P25713) Metallothionein-1F (P04733) Metallothionein-1E (P04732) Metallothionein-1X (P80297) Metallothionein-1A (P04731) Metallothionein-1B (P07438) Metallothionein-1M (Q8N339) Metallothionein-4 (P47944) Metallothionein-1L (Q93083) Arsenite methyltransferase (Q9HBK9) (L92)</interacting-proteins>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id>C074483</ctd-id>
  <stitch-id>Methyldichloroarsine</stitch-id>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins>
Arsenite methyltransferase (Q9HBK9) 
(L92)</metabolizing-proteins>
  <transporting-proteins>Metallothionein-2 (P02795) 
Metallothionein-1G (P13640) 
Metallothionein-1H (P80294) 
Metallothionein-3 (P25713) 
Metallothionein-1F (P04733) 
Metallothionein-1E (P04732) 
Metallothionein-1X (P80297) 
Metallothionein-1A (P04731) 
Metallothionein-1B (P07438) 
Metallothionein-1M (Q8N339) 
Metallothionein-4 (P47944) 
Metallothionein-1L (Q93083) 
(L92)</transporting-proteins>
  <moldb-smiles>C[As](Cl)Cl</moldb-smiles>
  <moldb-formula>CH3AsCl2</moldb-formula>
  <moldb-inchi>InChI=1S/CH3AsCl2/c1-2(3)4/h1H3</moldb-inchi>
  <moldb-inchikey>VXRMBBLRHSRVDK-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">160.862</moldb-average-mass>
  <moldb-mono-mass type="decimal">159.882776927</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Gas</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>55089</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM001131</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00126183</susdat-id>
  <iupac>dichloro(methyl)arsane</iupac>
  <moldb-polar-surface-area>0</moldb-polar-surface-area>
  <moldb-refractivity>18.2183</moldb-refractivity>
  <moldb-polarizability>10.197434486627158</moldb-polarizability>
  <moldb-rotatable-bond-count>0</moldb-rotatable-bond-count>
  <moldb-acceptor-count>0</moldb-acceptor-count>
  <moldb-donor-count>0</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic nil="true"/>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>0</moldb-number-of-rings>
  <moldb-alogps-logp>1.48</moldb-alogps-logp>
  <moldb-alogps-logs>-0.84</moldb-alogps-logs>
  <moldb-alogps-solubility>2.33e+01 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organometallic compounds</superklass>
  <klass>Organometalloid compounds</klass>
  <subklass>Organoarsenic compounds</subklass>
  <paper-count type="integer">3</paper-count>
  <sync-id>CED0029076</sync-id>
  <structure-inchikey>VXRMBBLRHSRVDK-UHFFFAOYSA-N</structure-inchikey>
  <structure-fingerprint>800000000000000000000000000000000000000000000000000002000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000400000040000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000</structure-fingerprint>
  <structure-pattern-fingerprint>4010000000040000000000000000008000000000000000000000000000000000400400000400000000000000000000000000000000000004200000000000001000002000000000000000000000000000000000000000040000000000000000000001001000000001000020040000004000000000000000000000000000002400000000000080000000000800180000000000000000800002000000040000000000000000000000000000000000000040000000000000000000000000000000080400000000000000000000000000000000000000000000000000400000001004000000000000010000000</structure-pattern-fingerprint>
  <structure-pickle type="binary" encoding="base64">776t3gAAAAAQAAAAAwAAAAAAAAAEAAAAAwAAAIABBgBgAAAAAQMhICAAAAAD
EQAgAAAAAREAIAAAAAELAAEAAQIAAQMAQgAAAAAXBAAAAAAAAAAW
</structure-pickle>
  <structure-indexed-at type="dateTime">2026-09-19T04:00:04Z</structure-indexed-at>
</compound>
