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Details

Stereochemistry ACHIRAL
Molecular Formula C2H7AsO2
Molecular Weight 137.9974
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CACODYLIC ACID

SMILES

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

InChI

InChIKey=OGGXGZAMXPVRFZ-UHFFFAOYSA-N
InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)

HIDE SMILES / InChI

Molecular Formula C2H7AsO2
Molecular Weight 137.9974
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Cacodylic acid also known as dimethylarsinic acid (DMA) has been used as a herbicide. As a part of agent blue it used to destroy broadleaf plants and trees, especially rice paddies during the Vietnam War. DMA is the major metabolite formed after exposure to tri- (arsenite) or pentavalent (arsenate) inorganic arsenic (iAs) via ingestion or inhalation in both humans and rodents. DMA induces an organ-specific lesion--single strand breaks in DNA. Mechanistic studies have suggested that this damage is due mainly to the peroxyl radical of DMA and production of active oxygen species by pulmonary tissues. Multi-organ initiation-promotion studies have demonstrated that DMA acts as a promotor of urinary bladder, kidney, liver and thyroid gland cancers in rats and as a promotor of lung tumors in mice. Thus it was shown, that DMA played a role in the carcinogenesis of inorganic arsenic.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Inorganic and methylated arsenic compounds induce cell death in murine macrophages via different mechanisms.
1998 Apr
Role of glutathione in dimethylarsinic acid-induced apoptosis.
2004 Aug 1
Gene expression profiling of responses to dimethylarsinic acid in female F344 rat urothelium.
2005 Nov 15
Arsenic methylation, GSTT1, GSTM1, GSTP1 polymorphisms, and skin lesions.
2007 Mar
Differential cytotoxic effects of arsenic compounds in human acute promyelocytic leukemia cells.
2009 Aug 15
Effect of topical dimethylarsinic acid on the expression of apoptosis-related proteins in mouse skin.
2012 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
Evaluation of gene expression changes in human primary uroepithelial cells following 24-hr exposures to inorganic arsenic and its methylated metabolites.
2013 Mar
Differential influences of various arsenic compounds on antioxidant defense system in liver and kidney of rats.
2013 Nov
SLCO1B1 variants and urine arsenic metabolites in the Strong Heart Family Study.
2013 Nov
Patents

Patents

Sample Use Guides

mutagenicity in rats: The purpose of present study is to evaluate the in vivo mutagenicities of dimethylarsinic acid (DMAV), (Cacodylic acid) and sodium arsenite (iAs) in rat urinary bladder epithelium and liver using gpt delta F344 rats. Ten-week old male gpt delta F344 rats were randomized into 3 groups and administered 0, 92 mg/L dimethylarsinic acid (DMAV), or 87mg/L sodium arsenite (iAs) (each 50mg/L As) for 13 weeks in the drinking water.
Route of Administration: Oral
In Vitro Use Guide
Gene damage in cultured human alveolar (L-132) cells induced by exposure to dimethylarsinic acid (DMAA) was stidued. DNA single-strand breaks and DNA-protein cross-links were induced by the treatment of L-132 cells with 10 mM DMAA. These kinds of damage appeared at 8 hr after start of exposure to DMAA. As regards DNA-protein cross-links, the DNA was found to bind not only to core histone proteins but also linker histone (H1) and nonhistone proteins. Furthermore, the cross-links were formed by the binding to serine or threonine residues of H1 or nonhistone proteins through phosphate moieties of the DNA. The induction of the alkali-labile sites in DNA in DMAA-treated L-132 cells was observed prior to that of DNA single-strand breaks and DNA-protein cross-links. As one of the alkali-labile sites in DNA, we estimated apurinic/apyrimidinic (AP) sites in DNA.
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:58:45 UTC 2023
Edited
by admin
on Fri Dec 15 14:58:45 UTC 2023
Record UNII
AJ2HL7EU8K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CACODYLIC ACID
MI   WHO-DD  
Systematic Name English
HYDROXYDIMETHYLARSINE OXIDE
Systematic Name English
DIMETHYLARSINIC ACID
Systematic Name English
DIMETHYLARSINIC ACID [IARC]
Common Name English
NSC-103115
Code English
Cacodylic acid [WHO-DD]
Common Name English
DIMETHYLARSENIC ACID [HSDB]
Common Name English
CACODYLIC ACID [MI]
Common Name English
Classification Tree Code System Code
IARC Dimethylarsinic acid
NCI_THESAURUS C737
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
EPA PESTICIDE CODE 12501
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
Code System Code Type Description
DRUG CENTRAL
3058
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
CHEBI
48765
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
SMS_ID
100000182554
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-883-4
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
PUBCHEM
2513
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
ALANWOOD
cacodylic acid
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
MESH
D002101
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
EVMPD
SUB196704
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
NSC
103115
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
MERCK INDEX
m2879
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY Merck Index
HSDB
360
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
NCI_THESAURUS
C80595
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
CAS
75-60-5
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID7020508
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
WIKIPEDIA
CACODYLIC ACID
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
FDA UNII
AJ2HL7EU8K
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
DRUG BANK
DB02994
Created by admin on Fri Dec 15 14:58:45 UTC 2023 , Edited by admin on Fri Dec 15 14:58:45 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT