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Details

Stereochemistry ACHIRAL
Molecular Formula 2CH4AsO3.Ca
Molecular Weight 318.003
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CALCIUM BIS(HYDROGEN METHYLARSONATE)

SMILES

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

InChI

InChIKey=PKOMXLRKGNITKG-UHFFFAOYSA-L
InChI=1S/2CH5AsO3.Ca/c2*1-2(3,4)5;/h2*1H3,(H2,3,4,5);/q;;+2/p-2

HIDE SMILES / InChI

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

Molecular Formula Ca
Molecular Weight 40.078
Charge 2
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
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
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
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
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
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 Sat Dec 16 08:00:41 GMT 2023
Edited
by admin
on Sat Dec 16 08:00:41 GMT 2023
Record UNII
O5A2M92125
Record Status Validated (UNII)
Record Version
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Name Type Language
CALCIUM BIS(HYDROGEN METHYLARSONATE)
Common Name English
CALCIUM HYDROGEN METHANEARSONATE
Systematic Name English
CALCIUM BIS(METHYLARSONATE)
Systematic Name English
CAMA
Common Name English
EPA PESTICIDE CHEMICAL CODE 013806
Code English
USAF AN-11
Code English
CALCIUM METHANEARSONATE
Systematic Name English
ARSONIC ACID, METHYL-, CALCIUM SALT (2:1)
Systematic Name English
CALCIUM ACID METHYL ARSONATE
Common Name English
J8.663K
Code English
MSMA, CALCIUM SALT
Common Name English
MAC
Common Name English
CALCIUM ACID METHANEARSONATE
Common Name English
SUPER CRAB-E-RAD-CALAR
Brand Name English
SUPER DAL-E-RAD-CALAR
Brand Name English
CALAR
Common Name English
METHANEARSONIC ACID, CALCIUM SALT (2:1)
Systematic Name English
Code System Code Type Description
FDA UNII
O5A2M92125
Created by admin on Sat Dec 16 08:00:41 GMT 2023 , Edited by admin on Sat Dec 16 08:00:41 GMT 2023
PRIMARY
PUBCHEM
73555192
Created by admin on Sat Dec 16 08:00:41 GMT 2023 , Edited by admin on Sat Dec 16 08:00:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID8034748
Created by admin on Sat Dec 16 08:00:41 GMT 2023 , Edited by admin on Sat Dec 16 08:00:41 GMT 2023
PRIMARY
CAS
5902-95-4
Created by admin on Sat Dec 16 08:00:41 GMT 2023 , Edited by admin on Sat Dec 16 08:00:41 GMT 2023
PRIMARY
ECHA (EC/EINECS)
227-598-8
Created by admin on Sat Dec 16 08:00:41 GMT 2023 , Edited by admin on Sat Dec 16 08:00:41 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY