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Dimethylarsinate

PubChem CID
167250
Structure
Dimethylarsinate_small.png
Molecular Formula
Synonyms
  • Dimethylarsinate
  • Cacodylate Ion
  • Cacodylate
  • 15132-04-4
  • Arsinic acid, dimethyl-, ion(1-)
Molecular Weight
136.99 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-11
Description
Dimethylarsinate is the arsenic oxoanion that is the conjugate base of dimethylarsinic acid. It is functionally related to an arsinate. It is a conjugate base of a dimethylarsinic acid.
Cacodylic acid is the chemical compound with the formula (CH3)2AsO2H. Derivatives of cacodylic acid, cacodylates, were frequently used as herbicides. For example, Agent Blue, one of the chemicals used during the Vietnam War, is a mixture of cacodylic acid and sodium cacodylate. Sodium cacodylate is frequently used as a buffering agent in the preparation and fixation of biological samples for transmission electron microscopy. Cacodylic acid is highly toxic by ingestion, inhalation, or skin contact. Once thought to be a byproduct of inorganic arsenic detoxification, it is now believed to have serious health consequences of its own. It has been shown to be teratogenic in rodents, most often causing cleft palate but also fetal fatality at high doses. It has been shown to be genotoxic in human cells, causing apoptosis and also decreased DNA production and shorter DNA strands. While not itself a strong carcinogen, cacodylic acid does promote tumors in the presence of carcinogens in organs such as the kidneys and liver. (Wikipedia).
An arsenical that has been used as a dermatologic agent and as an herbicide.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Dimethylarsinate.png

1.2 3D Status

Conformer generation is disallowed since MMFF94s unsupported element

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

dimethylarsinate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)/p-1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

OGGXGZAMXPVRFZ-UHFFFAOYSA-M
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[As](=O)(C)[O-]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C2H6AsO2-
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 ChEBI ID

2.3.3 DSSTox Substance ID

2.3.4 Nikkaji Number

2.3.5 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Acid, Cacodylic
  • Acid, Dimethylarsinic
  • Cacodylate
  • Cacodylic Acid
  • Dimethylarsinate
  • Dimethylarsinic Acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
136.99 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
136.958374 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
136.958374 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
40.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
5
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
-1
Reference
Computed by PubChem
Property Name
Complexity
Property Value
53.8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

Instrument Name
Bruker WH-90
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Herbicides
Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)

7.2 Metabolism / Metabolites

Arsenic and its metabolites are primarily excreted in the urine. (L2)
L2: ATSDR - Agency for Toxic Substances and Disease Registry (2007). Toxicological profile for arsenic. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp2.html

7.3 Biochemical Reactions

7.4 Transformations

8 Use and Manufacturing

8.1 Uses

Dimethylarsinic acid is used as an herbicide and pesticide. (L180)
L180: Wikipedia. Cacodylic acid. Last Updated 22 January 2009. http://en.wikipedia.org/wiki/Cacodylic_acid

9 Toxicity

9.1 Toxicological Information

9.1.1 Toxicity Summary

Arsenic and its metabolites disrupt ATP production through different mechanisms. At the level of the citric acid cycle, arsenic inhibits the pyruvate dehydrogenase and uncouples the oxidative phosphorylation by competing with phosphate. This leads to inhibition of energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is increased, leading to oxidative stress due to the formation of reactive oxygen species. Arsenic's carginogenicity is influenced by the arsenical binding of tubulin, which results in aneuploidy, polyploidy and mitotic arrests. The binding of other arsenic protein targets may also cause altered DNA repair enzyme activity, altered DNA methylation patterns and cell proliferation. (T1, A17)
A17: Kitchin KT, Wallace K: The role of protein binding of trivalent arsenicals in arsenic carcinogenesis and toxicity. J Inorg Biochem. 2008 Mar;102(3):532-9. doi: 10.1016/j.jinorgbio.2007.10.021. Epub 2007 Nov 22. PMID:18164070
T1: Klaassen C and Watkins J (2003). Casarett and Doull's Essentials of Toxicology. New York, NY: McGraw-Hill.

9.1.2 Carcinogen Classification

Carcinogen Classification
2B, possibly carcinogenic to humans. (L135)

9.1.3 Health Effects

Arsenic poisoning can lead to death from multi-system organ failure, probably from necrotic cell death, not apoptosis. Arsenic is also a known carcinogen, especially in skin, liver, bladder and lung cancers. (T1, L20)
L20: Wikipedia. Arsenic toxicity. Last Updated 22 February 2009. http://en.wikipedia.org/wiki/Arsenic_toxicity
T1: Klaassen C and Watkins J (2003). Casarett and Doull's Essentials of Toxicology. New York, NY: McGraw-Hill.

9.1.4 Exposure Routes

Oral (L2) ; inhalation (L2); dermal (L2)
L2: ATSDR - Agency for Toxic Substances and Disease Registry (2007). Toxicological profile for arsenic. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp2.html

9.1.5 Symptoms

Exposure to lower levels of arsenic can cause nausea and vomiting, decreased production of red and white blood cells, abnormal heart rhythm, damage to blood vessels, and a sensation of “pins and needles” in hands and feet. Breathing high levels of inorganic arsenic can provoque sore throat or irritated lungs. Arsenic also affects the brain, causing neurological disturbances such as headaches, confusion, and drowsiness. (A1)
A1: Croal LR, Gralnick JA, Malasarn D, Newman DK: The genetics of geochemistry. Annu Rev Genet. 2004;38:175-202. PMID:15568975

9.1.6 Toxicity Data

LD50: 644 mg/kg (Oral, Rat) (T14) LD50: 720 mg/kg (Intraperitoneal, Rat) (T32)
T14: Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
T32: Verschueren K (1983). Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co.

9.1.7 Treatment

Arsenic poisoning can be treated by chelation therapy, using chelating agents such as dimercaprol, EDTA or DMSA. Charcoal tablets may also be used for less severe cases. In addition, maintaining a diet high in sulfur helps eliminate arsenic from the body. (L20)
L20: Wikipedia. Arsenic toxicity. Last Updated 22 February 2009. http://en.wikipedia.org/wiki/Arsenic_toxicity

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Chemical Co-Occurrences in Literature

10.4 Chemical-Gene Co-Occurrences in Literature

10.5 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 Chemical Co-Occurrences in Patents

11.3 Chemical-Disease Co-Occurrences in Patents

11.4 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Protein Bound 3D Structures

12.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

12.2 Chemical-Target Interactions

12.3 Pathways

13 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

15 Classification

15.1 MeSH Tree

15.2 ChEBI Ontology

15.3 ChemIDplus

15.4 NORMAN Suspect List Exchange Classification

15.5 EPA DSSTox Classification

15.6 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. BindingDB
    LICENSE
    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
  2. Therapeutic Target Database (TTD)
  3. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
  4. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  5. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  6. EPA DSSTox
    Arsinic acid, dimethyl-, ion(1-)
    https://comptox.epa.gov/dashboard/DTXSID60164758
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. ChEBI
  8. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  9. Japan Chemical Substance Dictionary (Nikkaji)
  10. Natural Product Activity and Species Source (NPASS)
  11. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Dimethylarsinate
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  12. Protein Data Bank in Europe (PDBe)
  13. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  14. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  15. SpectraBase
  16. Wikidata
  17. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  18. PubChem
  19. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS