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Details

Stereochemistry ACHIRAL
Molecular Formula CH4AsO3.H4N
Molecular Weight 157.0007
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMMONIUM METHANEARSONATE

SMILES

[NH4+].C[As](O)([O-])=O

InChI

InChIKey=MLWMZTRCXNCAPF-UHFFFAOYSA-N
InChI=1S/CH5AsO3.H3N/c1-2(3,4)5;/h1H3,(H2,3,4,5);1H3

HIDE SMILES / InChI

Molecular Formula H3N
Molecular Weight 17.0305
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula CH5AsO3
Molecular Weight 139.9702
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Arsenic exposure disrupts the normal function of the FA/BRCA repair pathway.
2014-11
Methylarsonous acid causes oxidative DNA damage in cells independent of the ability to biomethylate inorganic arsenic.
2014-02
SLCO1B1 variants and urine arsenic metabolites in the Strong Heart Family Study.
2013-11
N-6-adenine-specific DNA methyltransferase 1 (N6AMT1) polymorphisms and arsenic methylation in Andean women.
2013-07
Evaluation of gene expression changes in human primary uroepithelial cells following 24-hr exposures to inorganic arsenic and its methylated metabolites.
2013-03
Methylation of arsenic by recombinant human wild-type arsenic (+3 oxidation state) methyltransferase and its methionine 287 threonine (M287T) polymorph: Role of glutathione.
2012-10-01
Alternative splicing variants of human arsenic (+3 oxidation state) methyltransferase.
2011-11-11
A pathway-based analysis of urinary arsenic metabolites and skin lesions.
2011-04-01
Adventitious arsenate reductase activity of the catalytic domain of the human Cdc25B and Cdc25C phosphatases.
2010-02-02
Effects of endogenous hydrogen peroxide and glutathione on the stability of arsenic metabolites in rat bile.
2008-10-01
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.
2007-06-15
Molecular mechanisms of the diabetogenic effects of arsenic: inhibition of insulin signaling by arsenite and methylarsonous acid.
2007-05
Arsenic methylation, GSTT1, GSTM1, GSTP1 polymorphisms, and skin lesions.
2007-03
Mammalian glucose permease GLUT1 facilitates transport of arsenic trioxide and methylarsonous acid.
2006-12-15
Chronic exposure to methylated arsenicals stimulates arsenic excretion pathways and induces arsenic tolerance in rat liver cells.
2006-05
Preventive mechanism of cellular glutathione in monomethylarsonic acid-induced cytolethality.
2005-08-01
Developmentally restricted genetic determinants of human arsenic metabolism: association between urinary methylated arsenic and CYT19 polymorphisms in children.
2005-06
Biokinetics and subchronic toxic effects of oral arsenite, arsenate, monomethylarsonic acid, and dimethylarsinic acid in v-Ha-ras transgenic (Tg.AC) mice.
2004-08
Genetic variation in genes associated with arsenic metabolism: glutathione S-transferase omega 1-1 and purine nucleoside phosphorylase polymorphisms in European and indigenous Americans.
2003-08
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.
2002-07-10
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:28:06 GMT 2025
Edited
by admin
on Mon Mar 31 19:28:06 GMT 2025
Record UNII
83358PW33I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMMONIUM METHANEARSONATE
Systematic Name English
ANSAR 157
Preferred Name English
METHYLARSONIC ACID AMMONIUM SALT
Common Name English
MAMA
Common Name English
MONOAMMONIUM METHANEARSONATE
Systematic Name English
AMMONIUM HYDROGEN METHYLARSONATE
Systematic Name English
METHANEARSONIC ACID, MONOAMMONIUM SALT
Systematic Name English
AMMONIUM METHYLARSONATE
Systematic Name English
ARSONIC ACID, METHYL-, MONOAMMONIUM SALT
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 13808
Created by admin on Mon Mar 31 19:28:06 GMT 2025 , Edited by admin on Mon Mar 31 19:28:06 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID4058029
Created by admin on Mon Mar 31 19:28:06 GMT 2025 , Edited by admin on Mon Mar 31 19:28:06 GMT 2025
PRIMARY
ALANWOOD
MAMA
Created by admin on Mon Mar 31 19:28:06 GMT 2025 , Edited by admin on Mon Mar 31 19:28:06 GMT 2025
PRIMARY
CAS
2321-53-1
Created by admin on Mon Mar 31 19:28:06 GMT 2025 , Edited by admin on Mon Mar 31 19:28:06 GMT 2025
PRIMARY
PUBCHEM
16851
Created by admin on Mon Mar 31 19:28:06 GMT 2025 , Edited by admin on Mon Mar 31 19:28:06 GMT 2025
PRIMARY
FDA UNII
83358PW33I
Created by admin on Mon Mar 31 19:28:06 GMT 2025 , Edited by admin on Mon Mar 31 19:28:06 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE