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Trimethylarsine

PubChem CID
68978
Structure
Trimethylarsine_small.png
Molecular Formula
Synonyms
  • Trimethylarsine
  • trimethylarsane
  • 593-88-4
  • Trimethylarsenic
  • Arsine, trimethyl-
Molecular Weight
120.03 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-11
Description
Trimethylarsine is an arsine that is arsane in which each of the hydrogens is substituted by a methyl group. It derives from a hydride of an arsane.
Trimethylarsine is an organic derivative of arsine, as well as the byproduct of microbial action on naturally occuring inorganic forms of arsenic. It is often used in the production of other organoarsenic compounds. Arsenic is a chemical element that has the symbol As and atomic number 33. It is a poisonous metalloid that has many allotropic forms: yellow (molecular non-metallic) and several black and grey forms (metalloids) are a few that are seen. Three metalloidal forms of arsenic with different crystal structures are found free in nature (the minerals arsenopyrite and the much rarer arsenolamprite and pararsenolamprite), but it is more commonly found as a compound with other elements. (T3, L388)
L388: Wikipedia. Trimethylarsine. Last Updated 19 May 2009. http://en.wikipedia.org/wiki/Trimethylarsine
T3: Emsley, John (2001). Nature's Building Blocks: An A-Z Guide to the Elements. Oxford: Oxford University Press.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Trimethylarsine.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

trimethylarsane
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C3H9As/c1-4(2)3/h1-3H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

HTDIUWINAKAPER-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

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

2.2 Molecular Formula

C3H9As
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 DSSTox Substance ID

2.3.6 KEGG ID

2.3.7 Metabolomics Workbench ID

2.3.8 Nikkaji Number

2.3.9 Wikidata

2.3.10 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

trimethylarsine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
120.03 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
0
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
119.992020 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
119.992020 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
0 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
4
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
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)

3.2 Experimental Properties

3.2.1 Physical Description

Colorless liquid; [Sigma-Aldrich MSDS]

3.3 Chemical Classes

Metals -> Arsenic Compounds, Organic

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 2
Source of Spectrum
NW-896-0-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
R2-1981-0-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

Arsenic is absorbed mainly by inhalation or ingestion, as to a lesser extent, dermal exposure. It is then distributed throughout the body, where it is reduced into arsenite if necessary, then methylated into monomethylarsenic (MMA) and dimethylarsenic acid (DMA) by arsenite methyltransferase. Arsenic and its metabolites are primarily excreted in the urine. Arsenic is known to induce the metal-binding protein metallothionein, which decreases the toxic effects of arsenic and other metals by binding them and making them biologically inactive, as well as acting as an antioxidant. (L20)
L20: Wikipedia. Arsenic toxicity. Last Updated 22 February 2009. http://en.wikipedia.org/wiki/Arsenic_toxicity

7.2 Biochemical Reactions

7.3 Transformations

8 Use and Manufacturing

8.1 Uses

Trimethylarsine is used in the microelectronics industry, the production of other organoarsenic compounds, and as a ligand in coordination chemistry. (L388)
L388: Wikipedia. Trimethylarsine. Last Updated 19 May 2009. http://en.wikipedia.org/wiki/Trimethylarsine

8.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Arsine, trimethyl-: ACTIVE
EPA TSCA Regulatory Flag
PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Flammable
Acute Toxic
Irritant
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H225 (40.9%): Highly Flammable liquid and vapor [Danger Flammable liquids]

H260 (59.1%): In contact with water releases flammable gases which may ignite spontaneously [Danger Substances and mixtures which in contact with water, emit flammable gases]

H261 (40.9%): In contact with water releases flammable gas [Danger Substances and mixtures which in contact with water, emit flammable gases]

H300 (59.1%): Fatal if swallowed [Danger Acute toxicity, oral]

H301 (40.9%): Toxic if swallowed [Danger Acute toxicity, oral]

H315 (59.1%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (59.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H331 (100%): Toxic if inhaled [Danger Acute toxicity, inhalation]

H335 (59.1%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P210, P223, P231+P232, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P335+P334, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P391, P402+P404, P403+P233, P403+P235, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 93 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Flam. Liq. 2 (40.9%)

Water-react. 1 (59.1%)

Water-react. 2 (40.9%)

Acute Tox. 2 (59.1%)

Acute Tox. 3 (40.9%)

Skin Irrit. 2 (59.1%)

Eye Irrit. 2 (59.1%)

Acute Tox. 3 (100%)

STOT SE 3 (59.1%)

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

9.1.3 Hazards Summary

Causes somnolence, tremor, and ataxia in inhalation lethal-concentration studies of mice; [RTECS] May cause irritation; [Sigma-Aldrich MSDS] See Triphenylarsine, Diethylarsine, and tert-Butylarsine.

9.2 Exposure Control and Personal Protection

9.2.1 Permissible Exposure Limit (PEL)

0.5 [mg/m3], as As

9.3 Regulatory Information

REACH Restricted Substance

Restricted substance: Trimethylarsine

EC: 209-815-8

Restriction condition document: PDF link

10 Toxicity

10.1 Toxicological Information

10.1.1 Toxicity Summary

Arsenic and its metabolites disrupt ATP production through several mechanisms. At the level of the citric acid cycle, arsenic inhibits pyruvate dehydrogenase and by competing with phosphate it uncouples oxidative phosphorylation, thus inhibiting energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is also increased, which might form reactive oxygen species and oxidative stress. 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.

10.1.2 Carcinogen Classification

Carcinogen Classification
3, not classifiable as to its carcinogenicity to humans. (L135)

10.1.3 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, esepcially 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.

10.1.4 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

10.1.5 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 burn (T1).
T1: Klaassen C and Watkins J (2003). Casarett and Doull's Essentials of Toxicology. New York, NY: McGraw-Hill.

10.1.6 Acute Effects

10.1.7 Toxicity Data

LC50 (mouse) = 20,500 ppm/4hr
LD50: 7870 mg/kg (Oral, Rouse) LC50: 20 500 ppm over 4 hours (Inhalation, Mouse) (L934)
L934: Strem Chemicals, Inc. (2007). Material Safety Data Sheet for Trimethylarsine. http://www.strem.com/catalog/printer.php?type=msds&catalog_number=98-1975

10.1.8 Minimum Risk Level

Acute Oral: 0.005 mg/kg/day (L134) Chronic Oral: 0.0003 mg/kg/day (L134) Chronic Inhalation: 0.01 mg/m3 (L134)
L134: ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/mrls/

10.1.9 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

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Wiley References

11.6 Chemical Co-Occurrences in Literature

11.7 Chemical-Gene Co-Occurrences in Literature

11.8 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

14 Classification

14.1 MeSH Tree

14.2 ChEBI Ontology

14.3 ChemIDplus

14.4 UN GHS Classification

14.5 NORMAN Suspect List Exchange Classification

14.6 EPA DSSTox Classification

14.7 EPA TSCA and CDR Classification

14.8 EPA Substance Registry Services Tree

14.9 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. 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/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA Chemicals under the TSCA
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. ChEBI
  8. Toxin and Toxin Target Database (T3DB)
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    http://www.t3db.ca/downloads
  9. Comparative Toxicogenomics Database (CTD)
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    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  10. Crystallography Open Database (COD)
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    https://creativecommons.org/publicdomain/zero/1.0/
  11. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  12. Japan Chemical Substance Dictionary (Nikkaji)
  13. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  14. Metabolomics Workbench
  15. 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/
    Trimethylarsine
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  16. 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
  17. SpectraBase
  18. Springer Nature
  19. Thieme Chemistry
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    https://creativecommons.org/licenses/by-nc-nd/4.0/
  20. Wikidata
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  24. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  25. GHS Classification (UNECE)
  26. EPA Substance Registry Services
  27. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  28. PATENTSCOPE (WIPO)
CONTENTS