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Details

Stereochemistry ACHIRAL
Molecular Formula CH3AsO3.2Na
Molecular Weight 183.9339
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DISODIUM METHYLARSONATE

SMILES

[Na+].[Na+].C[As]([O-])([O-])=O

InChI

InChIKey=SDIXRDNYIMOKSG-UHFFFAOYSA-L
InChI=1S/CH5AsO3.2Na/c1-2(3,4)5;;/h1H3,(H2,3,4,5);;/q;2*+1/p-2

HIDE SMILES / InChI
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Promoting effects of monomethylarsonic acid, dimethylarsinic acid and trimethylarsine oxide on induction of rat liver preneoplastic glutathione S-transferase placental form positive foci: a possible reactive oxygen species mechanism.
2002 Jul 10
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
Biokinetics and subchronic toxic effects of oral arsenite, arsenate, monomethylarsonic acid, and dimethylarsinic acid in v-Ha-ras transgenic (Tg.AC) mice.
2004 Aug
Preventive mechanism of cellular glutathione in monomethylarsonic acid-induced cytolethality.
2005 Aug 1
Developmentally restricted genetic determinants of human arsenic metabolism: association between urinary methylated arsenic and CYT19 polymorphisms in children.
2005 Jun
Chronic exposure to methylated arsenicals stimulates arsenic excretion pathways and induces arsenic tolerance in rat liver cells.
2006 May
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
N-6-adenine-specific DNA methyltransferase 1 (N6AMT1) polymorphisms and arsenic methylation in Andean women.
2013 Jul
Evaluation of gene expression changes in human primary uroepithelial cells following 24-hr exposures to inorganic arsenic and its methylated metabolites.
2013 Mar
SLCO1B1 variants and urine arsenic metabolites in the Strong Heart Family Study.
2013 Nov
Methylarsonous acid causes oxidative DNA damage in cells independent of the ability to biomethylate inorganic arsenic.
2014 Feb
Arsenic exposure disrupts the normal function of the FA/BRCA repair pathway.
2014 Nov
Patents

Sample Use Guides

In Vivo Use Guide
Methylarsonate is considered only slightly toxic, having an oral LD50 of 2200 mg/Kg for rats.
Route of Administration: Oral
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.
Name Type Language
DISODIUM METHYLARSONATE
Systematic Name English
DSMA
Common Name English
METHANEARSONIC ACID DISODIUM SALT [MI]
Common Name English
Methylarsonate disodium [WHO-DD]
Common Name English
DISODIUM METHANEARSONATE [HSDB]
Common Name English
Disodium methanearsonate [WHO-DD]
Common Name English
DISODIUM METHANEARSONATE
HSDB   WHO-DD  
Systematic Name English
NSC-5270
Code English
METHYLARSONATE DISODIUM
WHO-DD  
Systematic Name English
METHANEARSONIC ACID DISODIUM SALT
MI  
Common Name English
METHYLARSONIC ACID, DISODIUM SALT
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 13802
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
Code System Code Type Description
MERCK INDEX
m7295
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY Merck Index
SMS_ID
100000076762
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY
WIKIPEDIA
Disodium methyl arsonate
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY
ALANWOOD
DSMA
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY
CAS
144-21-8
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY
NSC
5270
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY
FDA UNII
7NK4BV40VN
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY
MESH
C020300
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID4032665
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY
PUBCHEM
8947
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY
HSDB
1701
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-620-7
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY
EVMPD
SUB13635MIG
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY
EVMPD
SUB14548MIG
Created by admin on Fri Dec 15 18:33:27 GMT 2023 , Edited by admin on Fri Dec 15 18:33:27 GMT 2023
PRIMARY