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Details

Stereochemistry ACHIRAL
Molecular Formula CH5AsO3
Molecular Weight 139.9702
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLARSONIC ACID

SMILES

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

InChI

InChIKey=QYPPRTNMGCREIM-UHFFFAOYSA-N
InChI=1S/CH5AsO3/c1-2(3,4)5/h1H3,(H2,3,4,5)

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
Mammalian glucose permease GLUT1 facilitates transport of arsenic trioxide and methylarsonous acid.
2006 Dec 15
Chronic exposure to methylated arsenicals stimulates arsenic excretion pathways and induces arsenic tolerance in rat liver cells.
2006 May
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
Arsenic methylation, GSTT1, GSTM1, GSTP1 polymorphisms, and skin lesions.
2007 Mar
Molecular mechanisms of the diabetogenic effects of arsenic: inhibition of insulin signaling by arsenite and methylarsonous acid.
2007 May
Effects of endogenous hydrogen peroxide and glutathione on the stability of arsenic metabolites in rat bile.
2008 Oct 1
Adventitious arsenate reductase activity of the catalytic domain of the human Cdc25B and Cdc25C phosphatases.
2010 Feb 2
A pathway-based analysis of urinary arsenic metabolites and skin lesions.
2011 Apr 1
Alternative splicing variants of human arsenic (+3 oxidation state) methyltransferase.
2011 Nov 11
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
METHYLARSONIC ACID
HSDB   ISO  
Systematic Name English
MONOMETHYLARSONIC ACID (SEE METHYLARSONIC ACID) [IARC]
Common Name English
Methanearsonic acid [WHO-DD]
Common Name English
METHYLARSINIC ACID
Systematic Name English
METHANEARSONIC ACID
MI   WHO-DD  
Systematic Name English
METHYLARSONIC ACID [IARC]
Common Name English
METHYLARSONIC ACID [ISO]
Common Name English
METHANEARSONIC ACID [MI]
Common Name English
METHYLARSONIC ACID [HSDB]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 628876
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
EPA PESTICIDE CODE 128876
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
Code System Code Type Description
CAS
124-58-3
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
MESH
C020300
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
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SMS_ID
100000076530
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
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HSDB
845
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
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EVMPD
SUB14533MIG
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
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MERCK INDEX
m7295
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY Merck Index
FDA UNII
J37VJ5709S
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
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ECHA (EC/EINECS)
204-705-6
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
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WIKIPEDIA
Methylarsonic acid
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
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CHEBI
29852
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY
PUBCHEM
8948
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
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EPA CompTox
DTXSID4020903
Created by admin on Fri Dec 15 15:04:51 GMT 2023 , Edited by admin on Fri Dec 15 15:04:51 GMT 2023
PRIMARY