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Record Information
Version1.0
Creation Date2009-03-06 18:58:29 UTC
Update Date2016-11-09 01:08:12 UTC
Accession NumberCHEM000256
Identification
Common NameTrimethylarsine
ClassSmall Molecule
DescriptionTrimethylarsine is an organic derivative of arsine, as well as the byproduct of microbial action on naturally occuring inorganic forms of arsenic. It is often used in the production of other organoarsenic compounds. 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, 9)
Contaminant Sources
  • IARC Carcinogens Group 3
  • T3DB toxins
Contaminant Type
  • Arsenic Compound
  • Industrial/Workplace Toxin
  • Natural Compound
  • Organic Compound
  • Organometallic
Chemical Structure
Thumb
Synonyms
ValueSource
(CH3)3AsChEBI
AsMe3ChEBI
Chemical FormulaC3H9As
Average Molecular Mass120.025 g/mol
Monoisotopic Mass119.992 g/mol
CAS Registry Number593-88-4
IUPAC Nametrimethylarsane
Traditional Nametrimethylarsine
SMILESC[As](C)C
InChI IdentifierInChI=1S/C3H9As/c1-4(2)3/h1-3H3
InChI KeyHTDIUWINAKAPER-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as trialkylarsanes. These are organoarsenic compounds containing a trivalent arsenic atom linked to three alkyl groups.
KingdomOrganic compounds
Super ClassOrganometallic compounds
ClassOrganometalloid compounds
Sub ClassOrganoarsenic compounds
Direct ParentTrialkylarsanes
Alternative Parents
Substituents
  • Trialkylarsane
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Arsine
  • 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
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-87.3°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility29.4 g/LALOGPS
logP1.13ALOGPS
logP1.48ChemAxon
logS-0.61ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity16.65 m³·mol⁻¹ChemAxon
Polarizability9.45 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, Positivesplash10-00di-0900000000-d19ffe11cd787448ba1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-658ae401b095c54d0135View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0900000000-658ae401b095c54d0135View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0900000000-68851a067274b5a48056View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-88f441db7b35ada9aa39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-aff9a20cd907668e7955View in MoNA
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4); dermal (4)
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. (5)
Toxicity ValuesLD50: 7870 mg/kg (Oral, Rouse) LC50: 20 500 ppm over 4 hours (Inhalation, Mouse) (10)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (8)
Uses/SourcesTrimethylarsine is used in the microelectronics industry, the production of other organoarsenic compounds, and as a ligand in coordination chemistry. (9)
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 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, 5)
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 (2).
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. (5)
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 LinkTrimethylarsine
Chemspider IDNot Available
ChEBI ID27130
PubChem Compound ID68978
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available