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Antimony potassium tartrate

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Antimony potassium tartrate trihydrate
Names
Other names
potassium antimonyl tartrate
emetic tartar
tartar emetic
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.116.333 Edit this at Wikidata
EC Number
  • 234-293-3
KEGG
  • 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
  • [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
Properties
K2Sb2(C4H2O6)2 · 3 H2O
Molar mass 667.87 g/mol
Appearance white crystalline powder
Density 2.6 g/cm3
8.3 g/100 mL (0 °C)
35.9 g/100 mL (100 °C)
Hazards
Lethal dose or concentration (LD, LC):
110 mg/kg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Antimony potassium tartrate, also known as potassium antimonyl tartrate, potassium antimontarterate, or emetic tartar, 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.

Emetic

500 mg tartar 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.[1][2][3]

Today, the compound is still used to induce vomiting in captured animals to study their diet.[4][5][6]

Medical

The first treatment application against trypanosomiasis was tested in 1906, and the compound's use to treat other tropical diseases was researched.[7] 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.[7][8] After British physician John Brian Christopherson's discovery in 1918 that antimony potassium tartrate could cure schistosomiasis, the antimonial drugs became widely used.[9][10][11] However, the injection of antimony potassium tartrate had severe side effects such as Adams–Stokes syndrome[12] 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.[13][14]

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.[15][16]

The New England Journal of Medicine[17] 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

Dissolving antimony oxide in tartaric acid is an easy way to obtain the compound.[18]

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 colourless crystals. [19]

References

  1. ^ McCallum, RI (1977). "President's address. Observations upon antimony". Proceedings of the Royal Society of Medicine. 70 (11): 756–63. PMC 1543508. PMID 341167.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ Christopherson, J.B. (1918). "The Successful Use of Antimony in Bilharziosis". The Lancet. 192 (4958): 325. doi:10.1016/S0140-6736(01)02807-0.
  10. ^ Crichton-Harris, Ann (2009-07-15). "Poison in small measure: Dr. Christopherson and the cure for bilharzia". ISBN 978-90-04-17541-9. {{cite journal}}: Cite journal requires |journal= (help)
  11. ^ 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.
  12. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 13447130, please use {{cite journal}} with |pmid=13447130 instead.
  13. ^ Hagan, Paul (2009). "Schistosomiasis – a rich vein of research". Parasitology. 136 (12): 1611–9. doi:10.1017/S003118200999093X. PMID 19691867.
  14. ^ Publishers, Bentham Science (October 1996). "The Antimonials". Current Medicinal Chemistry. pp. 304–305.
  15. ^ Silverman, Matt (2003). Loony lawsuits. Barnes & Noble Books. p. 81. ISBN 9780760738931. Retrieved 1 January 2013.
  16. ^ "United States v. 111/4 DOZEN PACKAGES, ETC..." Retrieved 1 January 2013.
  17. ^ 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.
  18. ^ Knapp, Fr. (1839). "Zur Bildungsgeschichte des Brechweinsteins". Annalen der Pharmacie. 32: 76. doi:10.1002/jlac.18390320107.
  19. ^ Frederick, George Mann (1952). Practical organic chemistry. England: Longmans, Green & Co. p. 115. ISBN 0582444071.

Further reading

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