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Record Information
Version1.0
Creation Date2009-03-06 18:58:31 UTC
Update Date2016-11-09 01:08:12 UTC
Accession NumberCHEM000266
Identification
Common NameSodium dimethylarsinate
ClassSmall Molecule
DescriptionSodium dimethylarsinate is an arsenic compound used as a drug in veterinary medicine to treat anaemia and eczema.
Contaminant Sources
  • Clean Air Act Chemicals
  • IARC Carcinogens Group 3
  • T3DB toxins
Contaminant Type
  • Arsenic Compound
  • Household Toxin
  • Organic Compound
  • Organometallic
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
((Dimethylarsino)oxy)sodium as-oxideChEBI
((Dimethylarsino)oxy)sodium-as-oxideChEBI
Cacodylate de sodiumChEBI
Cacodylic acid sodium saltChEBI
Dimethylarsinic acid sodium saltChEBI
Hydroxydimethylarsine oxide, sodium saltChEBI
Sodium cacodylateChEBI
Sodium dimethyl arsinateChEBI
Sodium dimethyl arsonideChEBI
Sodium salt OF cacodylic acidChEBI
Cacodylic acid de sodiumGenerator
Cacodylate sodium saltGenerator
Dimethylarsinate sodium saltGenerator
Sodium cacodylic acidGenerator
Sodium dimethyl arsinic acidGenerator
Sodium salt OF cacodylateGenerator
Sodium dimethylarsinic acidGenerator
Chemical FormulaC2H6AsNaO2
Average Molecular Mass159.979 g/mol
Monoisotopic Mass159.948 g/mol
CAS Registry Number124-65-2
IUPAC Namesodium dimethylarsinate
Traditional Namecacodylic acid sodium salt
SMILESC[As](C)(=O)O[Na]
InChI IdentifierInChI=1S/C2H7AsO2.Na/c1-3(2,4)5;/h1-2H3,(H,4,5);/q;+1/p-1
InChI KeyIHQKEDIOMGYHEB-UHFFFAOYSA-M
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.
KingdomOrganic compounds
Super ClassOrganometallic compounds
ClassOrganometalloid compounds
Sub ClassOrganoarsenic compounds
Direct ParentPentaorganoarsanes
Alternative Parents
Substituents
  • Pentaorganoarsane
  • Alkylarsine oxide
  • Oxygen-containing organoarsenic compound
  • Organic alkali metal salt
  • Organic metalloid salt
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic sodium salt
  • Organic salt
  • 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
Applications
Biological RolesNot Available
Chemical Roles
Physical Properties
StateSolid
AppearanceColorless or light yellow solid.
Experimental Properties
PropertyValue
Melting Point200°C
Boiling PointNot Available
Solubility2000 mg/mL at 25°C [TOMLIN,C (1997)]
Predicted Properties
PropertyValueSource
Water Solubility81.5 g/LALOGPS
logP0.02ALOGPS
logP0.68ChemAxon
logS-0.29ALOGPS
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity14.68 m³·mol⁻¹ChemAxon
Polarizability10.7 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, Positivesplash10-03di-0900000000-0993c0623dab9641a32fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-0876109ccae392548437View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-2900000000-b84793119de751f7f518View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-0900000000-2db0d3913727a956a23dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-9800000000-07ad2a14b539ac838bc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-0900000000-3649cea90d2cd4061c46View in MoNA
1D NMR1H NMR SpectrumNot Available
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 carcinogenicity 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. (3, 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: 2600 mg/kg (Oral, Rat)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (6)
Uses/SourcesSodium dimethylarsinate is used as a drug in veterinary medicine to treat anaemia and eczema, and is also an herbicide.
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 EffectsHypovolemia from capillary leakage (third-spacing of fluids) is a common, serious, early effect. Muscle cramps, facial edema, bronchitis, dyspnea, chest pain, dehydration, intense thirst, and fluid-electrolyte disturbances are also common following significant exposures. A garlic-like odor of the breath and feces may also occur. After absorption, arsenic may cause multi-organ failure by inhibiting sulfhydryl-containing enzymes. Encephalopathy, with headache, lethargy, mental confusion, hallucinations, emotional lability, memory loss and delirium may occur; seizures, stupor, convulsions, coma, and death may follow within 24 hours of a severe acute exposure. Dysrhythmias (particularly QTc prolongation and torsade de pointes), cardiomyopathy, ARDS, hepatitis, rhabdomyolysis, hemolysis, and renal failure may develop over several days. The sequence of chronic poisoning involves hyperpigmentation, and eczematoid and allergic dermatitis. muscle fasciculations; gross tremors; ataxia; incoordination; and mental confusion. Muscular weakness, limb tenderness and difficulty walking may follow. The final phase consists of peripheral sensory neuropathy of the hands and feet. That may be associated with a motor neuropathy as well (2).
SymptomsInitial signs and symptoms of arsenic ingestion include burning lips, throat constriction and dysphagia, followed by excruciating abdominal pain, hemorrhagic gastritis, gastroenteritis, severe nausea, projectile voting, profuse "rice water-like" diarrhea, with hypovolemia that may result in hypotension and an irregular pulse. The sequence of chronic poisoning involves weakness, anorexia, hepatomegaly, jaundice, and gastrointestinal complaints, followed by conjunctivitis, irritation of the throat and respiratory tract. ther effects of chronic exposure include conjunctivitis with irritation and lacrimation; hair, skin and nail changes; hyperkeratosis of feet and hands; and melanosis, with pigment spots in corneal and conjunctival epithelium. Peripheral nervous system symptoms may include numbness, burning, and tingling of the hands and feet; pain; paresthesias; tenderness (2).
TreatmentAggressive decontamination with gastric lavage is recommended if the patient has consumed a potentially life-threatening dose and if the patient is not vomiting. Administer charcoal as a slurry (2).
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 LinkNot Available
Chemspider IDNot Available
ChEBI ID62956
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=161110