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
SMILES
C[As](C)(O)=O
InChI
InChIKey=OGGXGZAMXPVRFZ-UHFFFAOYSA-N
InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11246143
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11246143
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: DNA Sources: https://www.ncbi.nlm.nih.gov/pubmed/7843116 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Inorganic and methylated arsenic compounds induce cell death in murine macrophages via different mechanisms. | 1998 Apr |
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Role of glutathione in dimethylarsinic acid-induced apoptosis. | 2004 Aug 1 |
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Gene expression profiling of responses to dimethylarsinic acid in female F344 rat urothelium. | 2005 Nov 15 |
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Arsenic methylation, GSTT1, GSTM1, GSTP1 polymorphisms, and skin lesions. | 2007 Mar |
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Differential cytotoxic effects of arsenic compounds in human acute promyelocytic leukemia cells. | 2009 Aug 15 |
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Effect of topical dimethylarsinic acid on the expression of apoptosis-related proteins in mouse skin. | 2012 May |
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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 |
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Evaluation of gene expression changes in human primary uroepithelial cells following 24-hr exposures to inorganic arsenic and its methylated metabolites. | 2013 Mar |
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Differential influences of various arsenic compounds on antioxidant defense system in liver and kidney of rats. | 2013 Nov |
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SLCO1B1 variants and urine arsenic metabolites in the Strong Heart Family Study. | 2013 Nov |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28007167
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7843116
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
Edited
Fri Dec 15 14:58:45 UTC 2023
by
admin
on
Fri Dec 15 14:58:45 UTC 2023
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Record UNII |
AJ2HL7EU8K
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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IARC | Dimethylarsinic acid | ||
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NCI_THESAURUS |
C737
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EPA PESTICIDE CODE |
12501
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3058
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48765
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100000182554
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200-883-4
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2513
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cacodylic acid
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D002101
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SUB196704
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103115
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m2879
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PRIMARY | Merck Index | ||
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360
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C80595
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75-60-5
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DTXSID7020508
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CACODYLIC ACID
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AJ2HL7EU8K
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DB02994
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |