ContaminantDB: 1,2-Bis(dimethylarsino)benzene

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

Record Information

Version

1.0

Creation Date

2009-06-19 21:58:34 UTC

Update Date

2026-08-18 01:48:10 UTC

Accession Number

CHEM001124

Identification

Common Name

1,2-Bis(dimethylarsino)benzene

Class

Small Molecule

Description

1,2-Bis(dimethylarsino)benzene (C10H16As2) is an exogenous organic compound with an average molecular weight of 286.08 g/mol. It exists as a liquid at room temperature. 1,2-Bis(dimethylarsino)benzene belongs to the benzene and substituted derivatives, a class of benzenoids within the organic compounds. The compound has been recorded as being found in or released from processed meats. The compound interacts with various protein targets. Arsenic binds to hemoglobin subunits alpha (HBA1) and beta (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). Additionally, arsenic binds to mitochondrial 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 mitochondrial dihydrolipoyllysine-residue acetyltransferase component (DLAT), the pyruvate dehydrogenase E1 component subunit beta (PDHB), and the pyruvate dehydrogenase E1 component subunit alpha in both somatic (PDHA1) and testis-specific (PDHA2) forms. 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. Furthermore, arsenic binding of XPA is believed to induce carcinogenesis by affecting DNA repair.

Contaminant Sources

IARC Carcinogens Group 3
T3DB toxins

Contaminant Type

Aromatic Hydrocarbon
Arsenic Compound
Industrial/Workplace Toxin
Organic Compound
Organometallic
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Phenylenebis(dimethylarsine)	ChEBI
2-Phenylene-bis-dimethylarsine	ChEBI
Diars	ChEBI
O-Phenylenebis(dimethylarsine)	ChEBI

Chemical Formula

C₁₀H₁₆As₂

Average Molecular Mass

286.077 g/mol

Monoisotopic Mass

285.968 g/mol

CAS Registry Number

13246-32-7

IUPAC Name

(2-dimethylarsanylphenyl)-dimethylarsane

Traditional Name

diArs

SMILES

C[As](C)C1=CC=CC=C1[As](C)C

InChI Identifier

InChI=1S/C10H16As2/c1-11(2)9-7-5-6-8-10(9)12(3)4/h5-8H,1-4H3

InChI Key

HUBWRAMPQVYBRS-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Tertiary arsine
Trivalent organic arsenic compound
Organic metalloid salt
Organopnictogen compound
Hydrocarbon derivative
Arsine
Organic salt
Organoarsenic compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organoarsenic compound (CHEBI:30628 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

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

Cololess liquid.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.85 g/L	ALOGPS
logP	3.37	ALOGPS
logP	3.63	ChemAxon
logS	-2.2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.09 m³·mol⁻¹	ChemAxon
Polarizability	23.16 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	splash10-000i-0090000000-1488f5910c4ba21462b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-e753ce0102b83130d504	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0190000000-c880fd1ea11a2c6091f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0290000000-ff93b046c0752cb055bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0290000000-87b0479e15e917d68fa5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ue9-1980000000-fde1eefa9bce149c4052	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. (7, 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

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.

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. (7, 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

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

1,2-Bis(dimethylarsino)benzene

Chemspider ID

Not Available

ChEBI ID

30628

PubChem Compound ID

83261

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

1,2-Bis(dimethylarsino)benzene (CHEM001124)

Structure for CHEM001124: 1,2-Bis(dimethylarsino)benzene