Antimony potassium tartrate trihydrate
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| Names |
Other names
potassium antimonyl tartrate
emetic tartar
tartar emetic |
| Identifiers |
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CAS Number
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28300-74-5 |
| ChEBI |
CHEBI:2761 |
| ChemSpider |
17214979 |
| EC Number |
234-293-3 |
| Jmol 3D image |
Interactive graph |
| KEGG |
C11340 |
| PubChem |
16682736 |
InChI
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InChI=1S/2C4H4O6.2K.3H2O.2Sb/c2*5-1(3(7)8)2(6)4(9)10;;;;;;;/h2*1-2H,(H,7,8)(H,9,10);;;3*1H2;;/q2*-2;2*+1;;;;2*+3/p-4
Key: WBTCZEPSIIFINA-UHFFFAOYSA-J
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SMILES
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[K+].[K+].[H]O[H].[H]O[H].[H]O[H].O=C1O[Sb-]23OC1C1O[Sb-]4(OC(C(O2)C(=O)O3)C(=O)O4)OC1=O
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| Properties |
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Chemical formula
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K2Sb2(C4H2O6)2 · 3 H2O |
| Molar mass |
667.87 g/mol |
| Appearance |
white crystalline powder |
| Density |
2.6 g/cm3 |
|
Solubility in water
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8.3 g/100 mL (0 °C)
35.9 g/100 mL (100 °C) |
| Hazards |
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EU classification (DSD)
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Xn N |
| R-phrases |
R20/22 R51/53 |
| S-phrases |
(S2) S61 |
| Lethal dose or concentration (LD, LC): |
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LD50 (Median dose)
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110 mg/kg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references |
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Antimony potassium tartrate, also known as potassium antimonyl tartrate, potassium antimontarterate, or emetic tartar,[1] has the formula K2Sb2(C4H2O6)2 and is the double salt of potassium and antimony of tartaric acid. The compound has long been known as a powerful emetic, and was used in the treatment of schistosomiasis and leishmaniasis.
Contents
- 1 Emetic
- 2 Medical
- 3 Preparation
- 4 References
- 5 Further reading
Emetic
Antimony potassium tartrate's potential as an emetic was known since the Middle Ages. The compound itself was considered toxic and therefore a different way to administer it was found. Cups made from pure antimony were used to store wine for 24 hours and then the resulting solution of antimony potassium tartrate in wine was consumed in small portions until the wanted emetic effect was reached.[2][3][4]
Today, the compound is still used to induce vomiting in captured animals to study their diet.[5][6][7]
Medical
The first treatment application against trypanosomiasis was tested in 1906, and the compound's use to treat other tropical diseases was researched.[8] The treatment of leishmania with antimony potassium tartrate started in 1913. After the introduction of antimony (V) containing complexes like sodium stibogluconate and meglumine antimoniate, the use of antimony potassium tartrate was phased out.[8][9] After British physician John Brian Christopherson's discovery in 1918 that antimony potassium tartrate could cure schistosomiasis, the antimonial drugs became widely used.[10][11][12] However, the injection of antimony potassium tartrate had severe side effects such as Adams–Stokes syndrome[13] and therefore alternative substances were under investigation. With the introduction and subsequent larger use of praziquantel in the 1970s, the use of antimony based treatments fell out of use.[14][15]
Tartar emetic was used in the late 19th and early 20th century in patent medicine as remedy for alcohol intoxication, and was first ruled ineffective in the United States in 1941, in United States v. 11 1/4 Dozen Packages of Articles Labeled in Part Mrs. Moffat’s Shoo-Fly Powders for Drunkenness.[16][17]
The New England Journal of Medicine[18] reported a case study of a patient whose wife secretly gave him a dose of a product called "tartaro emetico" which contained trivalent antimony (antimony potassium tartrate) and is sold in Central America as an aversive treatment for alcohol abuse. The patient, who had been out drinking the night before, developed persistent vomiting shortly after being given orange juice with the drug. When admitted to the hospital, and later in the ICU, he experienced severe chest pains, cardiac abnormalities, renal and hepatic toxicity, and nearly died. The Journal reports that "Two years later, he [the patient] reports complete abstinence from alcohol."
Preparation
Antimony potassium tartrate can be prepared by refluxing a solution of potassium hydrogen tartrate and antimony trioxide for 15 minutes. The hot mixture is then filtered and crystals of Antimony potassium tartrate precipitates out as a colourless crystals.[19][20]
References
- ^ Sun, H.; Yan, S.C.; Cheng, W.S. (2003). "Interaction of antimony tartrate with the tripeptide glutathione". European Journal of Biochemistry 267 (17): 5450–5457. doi:10.1046/j.1432-1327.2000.01605.x.
- ^ McCallum, RI (1977). "President's address. Observations upon antimony". Proceedings of the Royal Society of Medicine 70 (11): 756–63. PMC: 1543508. PMID 341167.
- ^ Thomson, SC (1926). "Antimonyall Cupps: Pocula Emetica or Calices Vomitorii". Proceedings of the Royal Society of Medicine 19 (Sect Hist Med): 122.2–128. PMC: 1948687. PMID 19985185.
- ^ Weiss, S.; Hatcher, RA (1922). "The Mechanism of the Vomiting Induced by Antimony and Potassium Tartrate (Tartar Emetic)". Journal of Experimental Medicine 37 (1): 97–111. doi:10.1084/jem.37.1.97. PMC: 2128404. PMID 19868716.
- ^ Poulin, B.; Lefebvre, G. t.; McNeil, R. (1994). "Effect and Efficiency of Tartar Emetic in Determining the Diet of Tropical Land Birds". The Condor 96 (1): 98–104. doi:10.2307/1369067. JSTOR 1369067.
- ^ Carlisle, J. D.; Holberton, R. L. (2006). "Relative Efficiency of Fecal versus Regurgitated Samples for Assessing Diet and the Deleterious Effects of a Tartar Emetic on Migratory Birds". Journal of Field Ornithology 77 (2): 126–135. doi:10.1111/j.1557-9263.2006.00032.x. JSTOR 27639314.
- ^ Diamond, Antony W.; Fayad, V. C.; McKinley, Peter S. (2007). "Commentary: Ipecac: An Improved Emetic for Wild Birds". Journal of Field Ornithology 78 (4): 436–439. doi:10.1111/j.1557-9263.2007.00136.x. JSTOR 27715221.
- ^ a b Low, George C. (1916). "The history of the use of intravenous injections of tartar emetic (Antimonium tartaratum) in tropical medicine". Transactions of the Royal Society of Tropical Medicine and Hygiene 10 (2): 37. doi:10.1016/S0035-9203(16)90068-3.
- ^ Navarro, Maribel; Gabbiani, Chiara; Messori, Luigi; Gambino, Dinorah (2010). "Metal-based drugs for malaria, trypanosomiasis and leishmaniasis: Recent achievements and perspectives". Drug Discovery Today 15 (23–24): 1070–8. doi:10.1016/j.drudis.2010.10.005. PMID 20974285.
- ^ Christopherson, J.B. (1918). "The Successful Use of Antimony in Bilharziosis". The Lancet 192 (4958): 325. doi:10.1016/S0140-6736(01)02807-0.
- ^ Crichton-Harris, Ann (2009-07-15). "Poison in small measure: Dr. Christopherson and the cure for bilharzia". ISBN 978-90-04-17541-9.
- ^ Sabah, A.A.; Fletcher, Cathy; Webbe, G.; Doenhoff, M.J. (1986). "Schistosoma mansoni: Chemotherapy of infections of different ages". Experimental Parasitology 61 (3): 294–303. doi:10.1016/0014-4894(86)90184-0. PMID 3086114.
- ^ t'Ao, S. C. (1957). "Cardiac manifestations of the toxic action of potassium antimony tartrate in schistosomiasis patients: Paroxysmal ventricular tachycardia and fibrillation". Chinese medical journal 75 (5): 365–378. PMID 13447130.
- ^ Hagan, Paul (2009). "Schistosomiasis – a rich vein of research". Parasitology 136 (12): 1611–9. doi:10.1017/S003118200999093X. PMID 19691867.
- ^ Publishers, Bentham Science (October 1996). "The Antimonials". Current Medicinal Chemistry. pp. 304–305.
- ^ Silverman, Matt (2003). Loony lawsuits. Barnes & Noble Books. p. 81. ISBN 9780760738931. Retrieved 1 January 2013.
- ^ "United States v. 111/4 DOZEN PACKAGES, ETC....". Retrieved 1 January 2013.
- ^ Macías Konstantopoulos, Wendy; Burns Ewald, Michele; Pratt, Daniel S. (2012). "Case 22-2012: A 34-Year-Old Man with Intractable Vomiting after Ingestion of an Unknown Substance". New England Journal of Medicine 367 (3): 259. doi:10.1056/NEJMcpc1111580.
- ^ Frederick, George Mann (1952). Practical organic chemistry. England: Longmans, Green & Co. p. 115. ISBN 0582444071.
- ^ Knapp, Fr. (1839). "Zur Bildungsgeschichte des Brechweinsteins". Annalen der Pharmacie 32: 76. doi:10.1002/jlac.18390320107.
Further reading
- Priesner, Claus (1997). "Basilius Valentinus und die Labortechnik um 1600". Berichte zur Wissenschaftsgeschichte 20 (2–3): 159. doi:10.1002/bewi.19970200205.
- Geoffroy, M.; Stack, T. (1751). "Observations on the Effects of the Vitrum Antimonii Ceratum, by Mons. Geoffroy, of the Royal Academy of Sciences, and F. R. S. Translated from the French by Tho. Stack, M. D. F. R. S". Philosophical Transactions 47: 273–278. doi:10.1098/rstl.1751.0042. JSTOR 105054.
- Berzelius, Jöns Jacob (1824). Lehrbuch der Chemie.
- Copus, Martinus (1569). Das Spißglas in ein Glas gegossen, das man Vitrum Antimonii nennt, ein wahrhafftige Gift vnd gantzgeferliche Artzney sey.
- The Technologist. 1861.
- "Captain Cook's Antimony Cup" (PDF). Vesalius, VII, 2: 62–64. 2001.
- Schneider, R. (1859). "Ueber einige Antimon-Verbindungen". Annalen der Physik und Chemie 184 (11): 407. Bibcode:1859AnP...184..407S. doi:10.1002/andp.18591841104.
- Groschuff, E. (1918). "Reines Antimon". Zeitschrift für anorganische und allgemeine Chemie 103: 164. doi:10.1002/zaac.19181030109.
- Soubeiran, E.; Capitaine, H. (1840). "Zur Geschichte der Weinsteinsäure". Journal für Praktische Chemie 19: 435. doi:10.1002/prac.18400190171.
- Pfaff, C. H. (1838). "Ueber Antimon-Wasserstoffgas und die davon abhängige Unsicherheit des von James Marsh entdeckten Verfahrens zur Entdeckung des Arseniks". Archiv der Pharmazie 64 (2): 169. doi:10.1002/ardp.18380640215.
- Zimmermann, E. (1930). "Das Antimon in der Chemotherapie". Klinische Wochenschrift 9: 27. doi:10.1007/BF01740712.
- Gress, Mary E.; Jacobson, Robert A. (1974). "X-ray and white radiation neutron diffraction studies of optically active potassium antimony tartrate, K2Sb2(d-C4H2O6)2·3H2O (tarter emetic)". Inorganica Chimica Acta 8: 209. doi:10.1016/S0020-1693(00)92617-3.