Trimethylarsine oxide (CHEM000267)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (69)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:31 UTC
Update Date2026-08-22 13:50:55 UTC
Accession NumberCHEM000267
Identification
Common NameTrimethylarsine oxide
ClassSmall Molecule
DescriptionTrimethylarsine oxide (C3H9AsO) is an exogenous organic compound with an average molecular weight of 136.02 g/mol. It exists as a solid at room temperature. Trimethylarsine oxide belongs to the organoarsenic compounds, a subclass of organometalloid compounds within the organic compounds. This compound interacts with 32 recorded protein targets. Arsenic binds to hemoglobin (HBA1, HBB), haptoglobin, the estrogen receptor (ESR1), the glucocorticoid receptor (NR3C1), and various forms of actin, including alpha skeletal muscle (ACTA1), aortic smooth muscle (ACTA2), cytoplasmic 1 (ACTB), and cytoplasmic 2 (ACTG1). Arsenic binding of XPA is believed to induce carcinogenesis by affecting DNA repair. Additionally, 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, affecting the dihydrolipoyllysine-residue acetyltransferase component of the pyruvate dehydrogenase complex (DLAT), the pyruvate dehydrogenase E1 component subunit alpha in somatic (PDHA1) and testis-specific (PDHA2) mitochondrial forms, and the pyruvate dehydrogenase E1 component subunit beta (PDHB). 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 might form oxidative stress and reactive oxygen species.
Contaminant Sources
  • IARC Carcinogens Group 3
  • T3DB toxins
Contaminant Type
  • Arsenic Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organometallic
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(CH3)3As=OChEBI
Chemical FormulaC3H9AsO
Average Molecular Mass136.025 g/mol
Monoisotopic Mass135.987 g/mol
CAS Registry Number4964-14-1
IUPAC Namedimethylarsorylmethane
Traditional Nametrimethylarsine oxide
SMILESC[As](C)(C)=O
InChI IdentifierInChI=1S/C3H9AsO/c1-4(2,3)5/h1-3H3
InChI KeyJWOWJQPAYGEFFK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentaorganoarsanes. These are organoarsenic compounds containing an arsenic compound that is pentasubstituted by only organic groups.
KingdomOrganic compounds
Super ClassOrganometallic compounds
ClassOrganometalloid compounds
Sub ClassOrganoarsenic compounds
Direct ParentPentaorganoarsanes
Alternative Parents
Substituents
  • Pentaorganoarsane
  • Trialkylarsane oxide
  • Alkylarsine oxide
  • Oxygen-containing organoarsenic compound
  • Organic metalloid salt
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
StateSolid
AppearanceNo data.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility42.1 g/LALOGPS
logP0.4ALOGPS
logP0.48ChemAxon
logS-0.51ALOGPS
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity18.78 m³·mol⁻¹ChemAxon
Polarizability10.19 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, Positivesplash10-000i-0900000000-4f64a7eff566c151142bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-e7a874bd941c32173641Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-19ed351c073bd679d5aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-0900000000-84b2ebaa425065eab732Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9400000000-1599752340e730342f6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-0900000000-904181911dafeffbe326Spectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3); dermal (3)
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. (4)
Toxicity ValuesLD50: 10.6 g/kg (Oral, Mouse) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (7)
Uses/SourcesNo data.
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (6) Chronic Oral: 0.0003 mg/kg/day (6) Chronic Inhalation: 0.01 mg/m3 (6)
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, 4)
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 burn (8).
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. (4)
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 ID27131
PubChem Compound ID104930
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available