砷甜菜碱

砷甜菜碱（英语：Arsenobetaine）是一种有机砷化合物，它是鱼类中砷的主要来源。^[1][2][3][4]砷甜菜碱是俗称甜菜碱的甘氨酸甜菜碱的砷类似物。砷甜菜碱的生物化学性质以及生物合成过程均与胆碱和甜菜碱相似。

砷甜菜碱
IUPAC名 2-(Trimethylarsaniumyl)acetate 2-(三甲基胂)乙酸酯
识别
CAS号	64436-13-1  Y
PubChem	47364
ChemSpider	43109
SMILES	C[As+](C)(C)CC(=O)[O-]
InChI	1/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
InChIKey	SPTHHTGLGVZZRH-UHFFFAOYAQ
Beilstein	3933180
EINECS	634-697-3
ChEBI	82392
RTECS	CH9750000
KEGG	C19331
MeSH	Arsenobetaine
性质
化学式	C5H11AsO2
摩尔质量	178.06 g·mol−1
危险性
GHS危险性符号
GHS提示词	Danger
H-术语	H301, H331, H400, H410
P-术语	P261, P264, P270, P271, P273, P301+310, P304+340, P311, P321, P330, P391, P403+233, P405, P501
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

砷甜菜碱是海洋生物系统中的一种常见物质。与许多有机砷化合物（如三甲基胂）不同，砷甜菜碱的毒性相对较低。^[5][6]

自1920年，人们就已经发现海鱼含有有机砷化合物。但直到1977年才确定了最主要存在形式砷甜菜碱的化学结构。^[7]

安全性

亚砷酸（As(OH)₃）的LD₅₀为34.5mg/kg（小鼠），而砷甜菜碱的LD₅₀超过10g/kg。^[8]

参考资料

1. Maher, B. Foreword: Research Front — Arsenic Biogeochemistry. Environmental Chemistry. 2005, 2 (3): 139–140. doi:10.1071/EN05063 .
2. Francesconi, K. A. Current Perspectives in Arsenic Environmental and Biological Research. Environmental Chemistry. 2005, 2 (3): 141–145. doi:10.1071/EN05042.
3. Adair, B. M.; Waters, S. B.; Devesa, V.; Drobna, Z.; Styblo, M.; Thomas, D. J. Commonalities in Metabolism of Arsenicals. Environmental Chemistry. 2005, 2 (3): 161–166 [2022-09-28]. doi:10.1071/EN05054. （原始内容存档于2020-08-17）.
4. Ng, J. C. Environmental Contamination of Arsenic and its Toxicological Impact on Humans. Environmental Chemistry. 2005, 2 (3): 146–160. doi:10.1071/EN05062.
5. Gaion A, Sartori D, Scuderi A, Fattorini D. Bioaccumulation and biotransformation of arsenic compounds in Hediste diversicolor (Muller 1776) after exposure to spiked sediments. Environmental Science and Pollution Research. 2014, 21 (9): 5952–5959 [2022-09-28]. PMID 24458939. S2CID 12568097. doi:10.1007/s11356-014-2538-z. （原始内容存档于2022-10-06）.
6. Bhattacharya, P.; Welch, A. H.; Stollenwerk, K. G.; McLaughlin, M. J.; Bundschuh, J.; Panaullah, G. Arsenic in the Environment: Biology and Chemistry. Science of the Total Environment. 2007, 379 (2–3): 109–120. Bibcode:2007ScTEn.379..109B. PMID 17434206. doi:10.1016/j.scitotenv.2007.02.037.
7. Edmonds, J. S.; Francesconi, K. A.; Cannon, J. R.; Raston, C. L.; Skelton, B. W.; White, A. H. Isolation, Crystal Structure and Synthesis of Arsenobetaine, the Arsenical Constituent of the Western Rock Lobster Panulirus longipes cygnus George. Tetrahedron Letters. 1977, 18 (18): 1543–1546. doi:10.1016/S0040-4039(01)93098-9.
8. Cullen, William R.; Reimer, Kenneth J. Arsenic speciation in the environment. Chemical Reviews. 1989, 89 (4): 713–764. doi:10.1021/cr00094a002. hdl:10214/2162 .

延伸阅读

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