二巯基丁二酸

二巯基丁二酸
	IUPAC名; meso-2,3-dimercaptosuccinic acid
别名	succimer, APRD01236 (Drugbank), Chemet
识别
CAS号	304-55-2
PubChem	2724354
ChemSpider	2006502
SMILES	O=C(O)[C@@H](S)[C@@H](S)C(=O)O;
InChI	1/C4H6O4S2/c5-3(6)1(9)2(10)4(7)8/h1-2,9-10H,(H,5,6)(H,7,8)/t1-,2+;
InChIKey	ACTRVOBWPAIOHC-XIXRPRMCBX
EINECS	259-952-2
性质
化学式	C4H6O4S2
摩尔质量	182.22 g/mol g·mol⁻¹
熔点	125 °C（398 K）
相关物质
相关化合物	酒石酸
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

2,3-二巯基丁二酸（Dimercaptosuccinic acid、英文缩写为：DMSA），别名2,3-二巯基琥珀酸，一般简称二巯基丁二酸，是一种有机硫化合物，常温下为白色结晶状粉末。因分子内含有两个巯基，所以它带有巯基化合物特有的臭味。二巯基丁二酸和它的钠盐都可以作为解毒剂通过口服或注射治疗重金属中毒。^[2] 二巯基丁二酸有两种非对映异构体，一种是内消旋体，另一种是外消旋体。内消旋体可作为螯合剂使用，常用其钠盐。

合成方法

可由丁炔二酸和硫代硫酸钠反应得到。^[3]

医疗用途

最初二巯基丁二酸的配合物二巯基丁二酸锑钾作为药物被Friedheim 等人引入到血吸虫病的治疗中，通过二巯基丁二酸的钾盐与金属锑离子的络合可以增加人体对锑的吸收，加强治疗效果。^[4] 1957年中国科学院上海药物研究所的梁猷毅等人首次报道了二巯基丁二酸的钠盐作为解毒剂可有效治疗酒石酸锑钾引起的重金属锑中毒，^[5]^[6] 随后又发现二巯基丁二酸及其钠盐可用于治疗砷、铅、汞、镉等重金属中毒，还可以作为促铜排泄药物治疗肝豆状核变性。^[7] 相对于二巯基丙醇来说，二巯基丁二酸的毒性很小，且对锑的解毒效果更好，因此常代替前者使用。^[2]^[8] 但是，尽管二巯基丁二酸可以穿过小鼠的血脑屏障，它却不能穿透人体的血脑屏障，^[9] 这使得二巯基丁二酸在人体重金属中毒治疗中有局限性，不能用于清除积存在中枢神经系统中的重金属元素。^[10]^[11]

参见

参考资料

^ Merck Index, 11th Edition, 8854.
^ ^2.0 ^2.1 Miller AL. Dimercaptosuccinic acid (DMSA), a non-toxic, water-soluble treatment for heavy metal toxicity.. Altern Med Rev. 1998, 3 (3): 199–207. PMID 9630737.
^ US 4550193,Lindemann, Martin K. O. & Lukenbach, Elvin R.,「Process for the preparation of 2,3-dimercaptosuccinic acid and its lower alkyl esters」,指定于Johnson & Johnson Baby Products
^ Friedheim, E. A. H., DaSilva, J. R., Martins, A. V. Treatment of schistosomiasis mansoni with antimony a.a'-dimercapto-potassium succinate (TWSb). Am. J. Trop. Med. Hyg. 1954, 3 (4): 714–27. PMID 13180832.
^ 寻找“还魂丹”――记解毒药二巯基丁二酸的研制. 上海发明协会. 2005-10-26 [2012-08-11]. （原始内容存档于2012-09-20）.
^ Liang, Y., Chu. C, Tsen, Y., Ting, K. Studies on antibilharzial drugs. Vl. The antidotal effects of sodium dimercaptosuccinate and BAL-glucoside against tartar emetic.. Acta Physiol. Sin. 1957, 21: 24–32.
^ Vasken Aposhian. DMSA and DMPS-water soluble antidotes for heavy metal poisoning.. Ann. Rev. Pharmacol Toxicol. 1983, 23: 193–213. PMID 6307120.
^ H. V. Aposhian. DMSA and DMPS--water soluble antidotes for heavy metal poisoning. Annual Review of Pharmacology and Toxicology. 1983, 23: 193–215 [2019-05-25]. ISSN 0362-1642. PMID 6307120. doi:10.1146/annurev.pa.23.040183.001205. （原始内容存档于2019-05-12）.
^ Aasath, Jan; Dag Jacobsen, Ole Andersen, Elsa Wickstrøm (March 1995). "Treatment of Mercury and Lead Poisonings with Dimercaptosuccinic Acid (DMSA) and Sodium Dimercaptopropanesulfonate (DMPS)". Analyst 120: 853ff.
^ Rooney, James. The role of thiols, dithiols, nutritional factors and interacting ligands in the toxicology of mercury. Toxicology. 2007, 234 (3): 145–156. PMID 17408840. doi:10.1016/j.tox.2007.02.016.
^ Guzzi, GianPaolo; Caterina A.M. La Porta. Molecular mechanisms triggered by mercury. Toxicology. 2008, 244 (1): 1–12. PMID 18077077. doi:10.1016/j.tox.2007.11.002.

拓展阅读

Aposhian, H.V.; Aposhian, M.M. Meso-2,3-dimercaptosuccinic acid: Chemical, pharmacological and toxicological properties of an orally effective metal chelating agent. Annual Review of Pharmacology and Toxicology. 1990, 30 (1): 279–306. PMID 2160791. doi:10.1146/annurev.pa.30.040190.001431.
寻找“还魂丹”――记解毒药二巯基丁二酸的研制（页面存档备份，存于互联网档案馆）

[1] Merck Index, 11th Edition, 8854.

[dmsa-2] 2.0 ^2.1 Miller AL. Dimercaptosuccinic acid (DMSA), a non-toxic, water-soluble treatment for heavy metal toxicity.. Altern Med Rev. 1998, 3 (3): 199–207. PMID 9630737.

[3] US 4550193,Lindemann, Martin K. O. & Lukenbach, Elvin R.,「Process for the preparation of 2,3-dimercaptosuccinic acid and its lower alkyl esters」,指定于Johnson & Johnson Baby Products

[4] Friedheim, E. A. H., DaSilva, J. R., Martins, A. V. Treatment of schistosomiasis mansoni with antimony a.a'-dimercapto-potassium succinate (TWSb). Am. J. Trop. Med. Hyg. 1954, 3 (4): 714–27. PMID 13180832.

[5] 寻找“还魂丹”――记解毒药二巯基丁二酸的研制. 上海发明协会. 2005-10-26 [2012-08-11]. （原始内容存档于2012-09-20）.

[6] Liang, Y., Chu. C, Tsen, Y., Ting, K. Studies on antibilharzial drugs. Vl. The antidotal effects of sodium dimercaptosuccinate and BAL-glucoside against tartar emetic.. Acta Physiol. Sin. 1957, 21: 24–32.

[7] Vasken Aposhian. DMSA and DMPS-water soluble antidotes for heavy metal poisoning.. Ann. Rev. Pharmacol Toxicol. 1983, 23: 193–213. PMID 6307120.

[8] H. V. Aposhian. DMSA and DMPS--water soluble antidotes for heavy metal poisoning. Annual Review of Pharmacology and Toxicology. 1983, 23: 193–215 [2019-05-25]. ISSN 0362-1642. PMID 6307120. doi:10.1146/annurev.pa.23.040183.001205. （原始内容存档于2019-05-12）.

[9] Aasath, Jan; Dag Jacobsen, Ole Andersen, Elsa Wickstrøm (March 1995). "Treatment of Mercury and Lead Poisonings with Dimercaptosuccinic Acid (DMSA) and Sodium Dimercaptopropanesulfonate (DMPS)". Analyst 120: 853ff.

[10] Rooney, James. The role of thiols, dithiols, nutritional factors and interacting ligands in the toxicology of mercury. Toxicology. 2007, 234 (3): 145–156. PMID 17408840. doi:10.1016/j.tox.2007.02.016.

[11] Guzzi, GianPaolo; Caterina A.M. La Porta. Molecular mechanisms triggered by mercury. Toxicology. 2008, 244 (1): 1–12. PMID 18077077. doi:10.1016/j.tox.2007.11.002.

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