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Name Description
id 67
T3DB ID T3D0075
Name Dimethylarsinate
Class SmallMolecule
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).
Categories "Pesticide", "Household Toxin", "Industrial/Workplace Toxin", "Food Toxin", "Synthetic Toxin"
Types "Arsenic Compound", "Organic Compound", "Pesticide", "Organometallic", "Food Toxin", "Metabolite", "Household Toxin", "Industrial/Workplace Toxin", "Synthetic Compound"
Synonyms "Ansar", "Arsan", "Bolate", "Bolls", "Cacodylate", "Cacodylic acid", "Chexmate", "Dimethylarsinic acid", "DMAA", "Erase", "Hydroxydimethylarsine oxide", "Moncide", "Phytar", "Phytar 560", "Silvisar"
CAS Number 15132-04-4
Chemical Formula C2H7AsO2
Average Molecular Mass 138.00
Monoisotopic Mass 137.97
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 InChIKey=OGGXGZAMXPVRFZ-UHFFFAOYSA-N
Kingdom Inorganic Compounds
Super Class Mixed Metal/Non-metal Compounds
Class Metalloid Salts
Sub Class
Direct Parent Organoarsenic Compounds
Alternate Parents "Organoarsenic Compounds", "Organic metalloid salts"
Geometric Description Aliphatic Acyclic Compounds
Substituents "organic metalloid moeity", "Aliphatic Acyclic Compound", "Organoarsenic Compound", "Organic Compound", "Organic metalloid salt", "Metalloid salt"
Descriptors "organoarsenic compound (ChEBI)", "Arsenical herbicides (KEGG)"
Status Detected and Quantified
Origin Exogenous
Cellular Locations "Cytoplasm", "Extracellular"
Biofluids "Saliva", "Urine"
Tissues
Pathways
State Solid
Appearance Colorless solid.
Melting Point 195°C
Boiling Point >200°C
Solubility 2000 mg/mL at 25 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
LogP
Route of Exposure Oral (L2) ; inhalation (L2); dermal (L2)
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. (T1, A17)
Metabolism Arsenic and its metabolites are primarily excreted in the urine. (L2)
Toxicity LD50: 644 mg/kg (Oral, Rat) (T14) LD50: 720 mg/kg (Intraperitoneal, Rat) (T32)
Lethal Dose
Carcinogenicity 2B, possibly carcinogenic to humans. (L135)
Uses/Sources Dimethylarsinic acid is used as an herbicide and pesticide. (L180)
Minimum Risk Level
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. (T1, L20)
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. (A1)
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. (L20)
DrugBank ID DB02994
HMDB ID HMDB11625
PubChem Compound ID 167250
ChEMBL ID
ChemSpider ID 146326
KEGG Compound ID C07308
UniProt ID 0
OMIM ID 0
ChEBI ID 16223
BioCyc ID DIMETHYLARSINATE
CTD ID D002101
Stitch ID Dimethylarsinic acid
PDB ID CAC
ACToR ID 516
Wikipedia Link http://en.wikipedia.org/wiki/Cacodylic acid
Creation Date 2009-03-06 18:58:02
Update Date 2014-12-24 20:21:03