ContaminantDB: Dimethylarsine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (69)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:29 UTC

Update Date

2026-08-22 09:57:52 UTC

Accession Number

CHEM000255

Identification

Common Name

Dimethylarsine

Class

Small Molecule

Description

Dimethylarsine is an exogenous liquid with the formula C2H7As and an average molecular weight of 106.00 g/mol. Dimethylarsine belongs to the organoarsenic compounds, a subclass of organometalloid compounds within the organic compounds. This compound has been recorded as being found in or released from fermentation processes for beer. The compound interacts with 32 recorded protein targets. Arsenic binds to actin, specifically ACTA1, ACTA2, ACTB, and ACTG1. It also binds to the estrogen receptor (ESR1), the glucocorticoid receptor (NR3C1), and haptoglobin. Binding to hemoglobin subunit alpha (HBA1) and hemoglobin subunit beta (HBB) is also observed. Furthermore, arsenic binds to mitochondrial glutathione reductase (GSR), which results in the inhibition of essential biochemical reactions, alteration of cellular redox status, and eventual cytotoxicity. Arsenic binding of XPA is believed to induce carcinogenesis by affecting DNA repair. Regarding energy production, arsenic disrupts ATP production through several mechanisms. It inhibits pyruvate dehydrogenase—specifically the PDHA1, PDHA2, and PDHB subunits and the DLAT component of the pyruvate dehydrogenase complex—at the level of the citric acid cycle. By competing with phosphate, it uncouples oxidative phosphorylation, thereby inhibiting ATP synthesis, mitochondrial respiration, and the energy-linked reduction of NAD+. Additionally, hydrogen peroxide production is increased, which may lead to oxidative stress and the formation of reactive oxygen species.

Contaminant Sources

IARC Carcinogens Group 3
T3DB toxins

Contaminant Type

Animal Toxin
Arsenic Compound
Natural Compound
Organic Compound
Organometallic

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂H₇As

Average Molecular Mass

105.999 g/mol

Monoisotopic Mass

105.976 g/mol

CAS Registry Number

593-57-7

IUPAC Name

dimethylarsane

Traditional Name

dimethylarsane

SMILES

C[AsH]C

InChI Identifier

InChI=1S/C2H7As/c1-3-2/h3H,1-2H3

InChI Key

HBNBMOGARBJBHS-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as trivalent organic arsenic compounds. These are organoarsenic compounds in which a carbon is linked to a trivalent arsenic atom.

Kingdom

Organic compounds

Super Class

Organometallic compounds

Class

Organometalloid compounds

Sub Class

Organoarsenic compounds

Direct Parent

Trivalent organic arsenic compounds

Alternative Parents

Substituents

Trivalent organic arsenic compound
Organopnictogen compound
Hydrocarbon derivative
Arsine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

No data.

Experimental Properties

Property	Value
Melting Point	-136.1°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	67.8 g/L	ALOGPS
logP	0.2	ALOGPS
logP	0.91	ChemAxon
logS	-0.19	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	11.9 m³·mol⁻¹	ChemAxon
Polarizability	7.44 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-d6430ba5d1135587f8de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-d4eed8058efb01006314	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-ed0d715edec060e2c97e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udr-8900000000-7e08d3bb3c9e90ece7a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1900000000-bf9255422f3d948860c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-1900000000-b4d55b8f984d61484173	Spectrum

Toxicity Profile

Route of Exposure

Oral (2) ; inhalation (2); dermal (2)

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. (8, 1)

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. (3)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (6)

Uses/Sources

Dimethylarsine is found in marine biological systems. (7)

Minimum Risk Level

Acute Oral: 0.005 mg/kg/day (5) Chronic Oral: 0.0003 mg/kg/day (5) Chronic Inhalation: 0.01 mg/m3 (5)

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. (8, 3)

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 burn (8).

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. (3)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

79055

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Dimethylarsine (CHEM000255)

Structure for CHEM000255: Dimethylarsine