Arsenobetaine

Arsenobetaine is an organoarsenic compound that is the main source of arsenic found in fish.[1][2][3][4] It is the arsenic analog of trimethylglycine, commonly known as betaine. The biochemistry and its biosynthesis are similar to those of choline and betaine.

Arsenobetaine

Names
Preferred IUPAC name 2-Trimethylarsoniumylacetate
Systematic IUPAC name 2-(Trimethylarsaniumyl)acetate
Identifiers
CAS Number	64436-13-1^Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	3933180
ChEBI	CHEBI:82392
ChEMBL	ChEMBL2448348
ChemSpider	43109^Y
ECHA InfoCard	100.162.654
EC Number	634-697-3
KEGG	C19331^Y
MeSH	Arsenobetaine
PubChem CID	47364
RTECS number	CH9750000
UNII	UWC1LS4V3I
CompTox Dashboard (EPA)	DTXSID0052833
InChI InChI=1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3^N Key: SPTHHTGLGVZZRH-UHFFFAOYSA-N^N InChI=1/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 Key: SPTHHTGLGVZZRH-UHFFFAOYAQ
SMILES C[As+](C)(C)CC(=O)[O-] C[As+](C)(C)CC([O-])=O
Properties
Chemical formula	C5H11AsO2
Molar mass	177.997501013 g mol^−1
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H331, H400, H410
GHS precautionary statements	P261, P264, P270, P271, P273, P301+310, P304+340, P311, P321, P330, P391, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Arsenobetaine is a common substance in marine biological systems and unlike many other organoarsenic compounds, such as arsenous acid and trimethylarsine, it is relatively non-toxic.[5]

It has been known since 1920 that marine fish contain organoarsenic compounds, but it was not until 1977 that the chemical structure of the most predominant compound arsenobetaine was determined.[6]

Safety

Whereas the arsenous acid (As(OH)₃) has an LD50 (mice) of 34.5 mg/kg (mice), the LD50 for the arsenobetaine exceeds 10 g/kg.[7]

References

1. Maher, B. (2005). "Foreword: Research Front — Arsenic Biogeochemistry". Environmental Chemistry. 2 (3): 139–140. doi:10.1071/EN05063.
2. Francesconi, K. A. (2005). "Current Perspectives in Arsenic Environmental and Biological Research". Environmental Chemistry. 2 (3): 141–145. doi:10.1071/EN05042.
3. Adair, B. M.; Waters, S. B.; Devesa, V.; Drobna, Z.; Styblo, M.; Thomas, D. J. (2005). "Commonalities in Metabolism of Arsenicals". Environmental Chemistry. 2 (3): 161–166. doi:10.1071/EN05054.
4. Ng, J. C. (2005). "Environmental Contamination of Arsenic and its Toxicological Impact on Humans". Environmental Chemistry. 2 (3): 146–160. doi:10.1071/EN05062.
5. Bhattacharya, P.; Welch, A. H.; Stollenwerk, K. G.; McLaughlin, M. J.; Bundschuh, J.; Panaullah, G. (2007). "Arsenic in the Environment: Biology and Chemistry". Science of the Total Environment. 379 (2–3): 109–120. doi:10.1016/j.scitotenv.2007.02.037. PMID 17434206.
6. Edmonds, J. S.; Francesconi, K. A.; Cannon, J. R.; Raston, C. L.; Skelton, B. W.; White, A. H. (1977). "Isolation, Crystal Structure and Synthesis of Arsenobetaine, the Arsenical Constituent of the Western Rock Lobster Panulirus longipes cygnus George". Tetrahedron Letters. 18 (18): 1543–1546. doi:10.1016/S0040-4039(01)93098-9.
7. Cullen, William R.; Reimer, Kenneth J. (1989). "Arsenic speciation in the environment". Chemical Reviews. 89 (4): 713–764. doi:10.1021/cr00094a002. hdl:10214/2162.

Further reading

• Craig, P. J. (2003). Organometallic Compounds in the Environment (2nd ed.). Chichester: John Wiley and Sons. p. 415. ISBN 978-0-471-89993-8.