ContaminantDB: Dimethylarsinate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (54)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:02 UTC

Update Date

2026-04-05 17:26:26 UTC

Accession Number

CHEM000071

Identification

Common Name

Dimethylarsinate

Class

Small Molecule

Description

Cacodylic acid is the chemical compound with the formula (CH3)2AsO2H. Derivatives of cacodylic acid, cacodylates, were frequently used as herbicides. For example, Agent Blue, one of the chemicals used during the Vietnam War, is a mixture of cacodylic acid and sodium cacodylate. Sodium cacodylate is frequently used as a buffering agent in the preparation and fixation of biological samples for transmission electron microscopy. Cacodylic acid is highly toxic by ingestion, inhalation, or skin contact. Once thought to be a byproduct of inorganic arsenic detoxification, it is now believed to have serious health consequences of its own. It has been shown to be teratogenic in rodents, most often causing cleft palate but also fetal fatality at high doses. It has been shown to be genotoxic in human cells, causing apoptosis and also decreased DNA production and shorter DNA strands. While not itself a strong carcinogen, cacodylic acid does promote tumors in the presence of carcinogens in organs such as the kidneys and liver. (Wikipedia).

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 2B
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Arsenic Compound
Food Toxin
Household Toxin
Industrial/Workplace Toxin
Metabolite
Organic Compound
Organometallic
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
[As(CH3)2O(OH)]	ChEBI
CACODYLIC ACID	ChEBI
Dimethylarsinate	ChEBI
Kakodylsaeure	ChEBI
Me2as(=o)OH	ChEBI
CACODYLate	Generator
Acid, dimethylarsinic	HMDB
Acid, cacodylic	HMDB
As,as-dimethylarsinic acid	HMDB
Dimethylarsenic acid	HMDB
Hydroxydimethylarsine oxide	HMDB
Dimethylarsinic acid	Generator

Chemical Formula

C₂H₇AsO₂

Average Molecular Mass

137.997 g/mol

Monoisotopic Mass

137.966 g/mol

CAS Registry Number

15132-04-4

IUPAC Name

dimethylarsinic acid

Traditional Name

ansar

SMILES

C[As](C)(O)=O

InChI Identifier

InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)

InChI Key

OGGXGZAMXPVRFZ-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.

Kingdom

Organic compounds

Super Class

Organometallic compounds

Class

Organometalloid compounds

Sub Class

Organoarsenic compounds

Direct Parent

Pentaorganoarsanes

Alternative Parents

Substituents

Pentaorganoarsane
Alkylarsine oxide
Oxygen-containing organoarsenic compound
Organic metalloid salt
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organoarsenic compound (CHEBI:48765 )
Arsenical herbicides (C07308 )

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

Solid

Appearance

Colorless solid.

Experimental Properties

Property	Value
Melting Point	195°C
Boiling Point	>200°C
Solubility	2000 mg/mL at 25 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

Predicted Properties

Property	Value	Source
Water Solubility	255 g/L	ALOGPS
logP	-0.48	ALOGPS
logP	-0.33	ChemAxon
logS	0.27	ALOGPS
pKa (Strongest Acidic)	6.22	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	15.9 m³·mol⁻¹	ChemAxon
Polarizability	9.18 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0900000000-aacd14a23122c6fead4f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-277740f35cf8f3db1076	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-3ba00e60d1b6e66786aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-8ae8b3e2664bfccfadce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-4605296babdf6148fcc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-5900000000-3be49b0b6e40807a58e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0900000000-0b14088c1c17aff4669f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-2f08307520e1e4ad4d1f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-6bc98922234d783edd28	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0900000000-d9daf50debedfc9ab847	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-723d8270a195a697561f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-0b6b8eda42b4b4a2c55e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gb9-0900000000-1ab81c1f902ad9956e3b	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0596-6900000000-c094738db14b7209da38	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (3) ; inhalation (3); dermal (3)

Mechanism of Toxicity

Arsenic and its metabolites disrupt ATP production through different mechanisms. At the level of the citric acid cycle, arsenic inhibits the pyruvate dehydrogenase and uncouples the oxidative phosphorylation by competing with phosphate. This leads to inhibition of energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is increased, leading to oxidative stress due to the formation of reactive oxygen species. 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, 2)

Metabolism

Arsenic and its metabolites are primarily excreted in the urine. (3)

Toxicity Values

LD50: 644 mg/kg (Oral, Rat) (9) LD50: 720 mg/kg (Intraperitoneal, Rat) (10)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (6)

Uses/Sources

Dimethylarsinic acid is used as an herbicide and pesticide. (7)

Minimum Risk Level

Not Available

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, especially in skin, liver, bladder and lung cancers. (8, 5)

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 “pins and needles” in hands and feet. Breathing high levels of inorganic arsenic can provoque sore throat or irritated lungs. Arsenic also affects the brain, causing neurological disturbances such as headaches, confusion, and drowsiness. (1)

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. (5)

Concentrations

Not Available

External Links

DrugBank ID

DB02994

HMDB ID

HMDB0011625

FooDB ID

FDB028327

Phenol Explorer ID

Not Available

KNApSAcK ID