Details
Stereochemistry | ACHIRAL |
Molecular Formula | CH3AsO3.2Na.6H2O |
Molecular Weight | 292.0255 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.O.O.O.[Na+].[Na+].C[As]([O-])([O-])=O
InChI
InChIKey=HPWNDUPOECNNLK-UHFFFAOYSA-L
InChI=1S/CH5AsO3.2Na.6H2O/c1-2(3,4)5;;;;;;;;/h1H3,(H2,3,4,5);;;6*1H2/q;2*+1;;;;;;/p-2
Methylarsonic acid, monosodium salt is an organoarsenic compound formed from the methylation of inorganic arsenic by living organisms. Methylarsonate is used as a contact herbicide in either the monosodium or disodium salt form. It goes by the trade names Weed-E-Rad, Ansar 170 H.C., Ansar 529 H.C., DiTac and others. Methylarsonate is considered only slightly toxic, having an oral LD50 of 2200 mg/Kg for rats. The inhalation risk is greater with LD50 Rats >20 mg. Long term studies with people exposed to organoarsenicals has shown an increased risk of skin cancer (Spiewak, 2001), lung cancer and some liver cancers, although some recent studies have shown some arsenic containing compounds (specifically Arsine trioxide) may have anticarcinogenic properties (Wang, 2001). In mammals, Methylarsonate is also an intermediate in the detoxification of inorganic arsenic. In the arsenate detoxification I pathway, arsenite reacts with S-adenosyl-L-methionine to produce methylarsonate and S-adenosyl-L-homocysteine. Arsenite methyltransferase catalyzes this reaction. Methylarsonate then reacts with 2 glutathione molecules to produce glutathione disulfide and methylarsonite. This reaction is catalyzed by methylarsonate reductase. Methylarsonate is an organic arsenic compound with adverse effects similar to those of arsenic trioxide. Methylarsonate was formerly included in some vitamin and mineral preparations. It was once used to treat tuberculosis, chorea, and other affections in which the cacodylates were used.
CNS Activity
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Genetic variation in genes associated with arsenic metabolism: glutathione S-transferase omega 1-1 and purine nucleoside phosphorylase polymorphisms in European and indigenous Americans. | 2003 Aug |
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Preventive mechanism of cellular glutathione in monomethylarsonic acid-induced cytolethality. | 2005 Aug 1 |
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Mammalian glucose permease GLUT1 facilitates transport of arsenic trioxide and methylarsonous acid. | 2006 Dec 15 |
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Elevation of 8-hydroxydeoxyguanosine and cell proliferation via generation of oxidative stress by organic arsenicals contributes to their carcinogenicity in the rat liver and bladder. | 2007 Jun 15 |
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Methylation of arsenic by recombinant human wild-type arsenic (+3 oxidation state) methyltransferase and its methionine 287 threonine (M287T) polymorph: Role of glutathione. | 2012 Oct 1 |
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Evaluation of gene expression changes in human primary uroepithelial cells following 24-hr exposures to inorganic arsenic and its methylated metabolites. | 2013 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.hmdb.ca/metabolites/HMDB0012258
Methylarsonate is considered only slightly toxic, having an oral LD50 of 2200 mg/Kg for rats.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21827493
Arsenate and arsenic trioxide (As(2) O(3) ) inhibited the proliferation of A375 and B16F10 cells significantly at concentration ranges of 0.1-20ug/ml (P<0.001), while the organic compounds arsenobetaine, arsenocholine, dimethylarsinic acid, methylarsonic acid, tetramethylarsonium and trimethylarsine oxide did not show any inhibitory effects even at 20ug/ml.
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5967-62-4
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