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Antimony potassium tartrate

November 23, 2023

Antimony potassium tartrate, also known as potassium antimonyl tartrate, potassium antimontarterate, or tartar emetic,[3] has the formula K2Sb2(C4H2O6)2. The compound has long been known as a powerful emetic, and was used in the treatment of schistosomiasis and leishmaniasis. It is used as a resolving agent. It typically is obtained as a hydrate.

Antimony potassium tartrate trihydrate

Ball-and-stick model of the bis(μ2-tartrato)-di-antimony anion,[1][2] [Sb2(C4H2O6)2]2−

  Carbon   Hydrogen

  Oxygen   Antimony
Names
Other names
potassium antimonyl tartrate
emetic tartar
tartar emetic
Identifiers
  • 28300-74-5 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:2761
ChemSpider
  • 17214979
ECHA InfoCard 100.116.333
EC Number
  • 234-293-3
1332600
KEGG
  • C11340
  • 16682736
UNII
  • DL6OZ476V3 Y
  • DTXSID3039240
  • 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+].O.O.O.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
GHS labelling:
Warning
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).

Medical edit

The first treatment application against trypanosomiasis was tested in 1906, and the compound's use to treat other tropical diseases was researched.[4] 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.[4][5] After British physician John Brian Christopherson's discovery in 1918 that antimony potassium tartrate could cure schistosomiasis, the antimonial drugs became widely used.[6][7][8] However, the injection of antimony potassium tartrate had severe side effects such as Adams–Stokes syndrome[9] and therefore alternative substances were under investigation. With the introduction and subsequent larger use of praziquantel in the 1970s, antimony-based treatments fell out of use.[10][11]

Tartar emetic was used in the late 19th and early 20th century in patent medicine as a 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.[12][13]

The New England Journal of Medicine reported[14] 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 use disorder. 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 intensive care unit, 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."

Emetic edit

 
500 mg tartar emetic

Antimony potassium tartrate's potential as an emetic has been 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.[15][16][17]

The compound is still used to induce vomiting in captured animals in order to study their diets.[18][19][20]

Preparation, structure, reactions edit

Antimony potassium tartrate is prepared by treating a solution of potassium hydrogen tartrate and antimony trioxide:

2 KOH + Sb2O3 + (HOCHCO2H)2 → K2Sb2(C4H2O6)2 + 3 H2O

With an excess of tartaric acid, the monoanionic monoantimony salt is produced:[2]

2 KOH + Sb2O3 + 4 (HOCHCO2H)2 → 2 KSb(C4H2O6)2 + 2 H2O

Antimony potassium tartrate has been the subject of several X-ray crystallography studies.[21][22][23][24][25][2] The core complex is an anionic dimer of antimony tartrate (Sb2(C4H2O6)22-) which is arranged in a large ring with the carbonyl groups pointing outwards. The complex has D2 molecular symmetry with two Sb(III) centers bonded in distorted square pyramids. Water and potassium ions are held within the unit cell but are not tightly bound to the dimer. The anion is a well-used resolving agent.[26]

 
Viewed along the x axis
 
Viewed along the y axis
 
Viewed along the z axis

Further reading edit

Of historic interest:

  • Frederick, George Mann (1952). Practical organic chemistry. England: Longmans, Green & Co. p. 115. ISBN 0-582-44407-1.
  • Knapp, Fr. (1839). "Zur Bildungsgeschichte des Brechweinsteins". Annalen der Pharmacie. 32: 76–85. doi:10.1002/jlac.18390320107.

References edit

  1. ^ Palenik, R.C.; Abboud, K.A.; Palenik, G.J. (2005). "CSD Entry: DKSBTR02: Di-potassium bis(μ2-tartrato)-di-antimony trihydrate". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/cc89ghh.
  2. ^ a b c Palenik, Ruth C.; Abboud, Khalil A.; Palenik, Gus J. (March 2005). "Bond valence sums and structural studies of antimony complexes containing Sb bonded only to O ligands". Inorganica Chimica Acta. 358 (4): 1034–1040. doi:10.1016/j.ica.2004.11.013.
  3. ^ 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. PMID 10951203.
  4. ^ 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): 37–42. doi:10.1016/S0035-9203(16)90068-3.
  5. ^ 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.
  6. ^ Christopherson, J.B. (1918). "The Successful Use of Antimony in Bilharziosis". The Lancet. 192 (4958): 325–327. doi:10.1016/S0140-6736(01)02807-0.
  7. ^ Crichton-Harris, Ann (2009-07-15). Poison in small measure: Dr. Christopherson and the cure for bilharzia. ISBN 978-90-04-17541-9.
  8. ^ 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.
  9. ^ 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.
  10. ^ Hagan, Paul (2009). "Schistosomiasis – a rich vein of research". Parasitology. 136 (12): 1611–9. doi:10.1017/S003118200999093X. PMID 19691867. S2CID 44279233.
  11. ^ Publishers, Bentham Science (October 1996). "The Antimonials". Current Medicinal Chemistry. pp. 304–305.
  12. ^ Silverman, Matt (2003). Loony lawsuits. Barnes & Noble Books. p. 81. ISBN 978-0-7607-3893-1. Retrieved 1 January 2013.
  13. ^ "United States v. 111/4 DOZEN PACKAGES, ETC..." Retrieved 1 January 2013.
  14. ^ 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): 259–68. doi:10.1056/NEJMcpc1111580. PMID 22808962.
  15. ^ McCallum, RI (1977). "President's address. Observations upon antimony". Proceedings of the Royal Society of Medicine. 70 (11): 756–63. doi:10.1177/003591577707001103. PMC 1543508. PMID 341167.
  16. ^ Thomson, SC (1926). "Antimonyall Cupps: Pocula Emetica or Calices Vomitorii". Proceedings of the Royal Society of Medicine. 19 (Sect Hist Med): 122.2–128. doi:10.1177/003591572601901707. PMC 1948687. PMID 19985185.
  17. ^ 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.
  18. ^ 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.
  19. ^ 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.
  20. ^ 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.
  21. ^ Grdenić, D.; Kamenar, B. (1 August 1965). "Structures involving unshared electron pairs: coordination of antimony in racemic potassium antimonyl tartrate". Acta Crystallographica. 19 (2): 197–199. doi:10.1107/S0365110X65003080.
  22. ^ Banerjee, A.K.; Chari, K.V.R. (September 1969). "Structure of potassium antimony tartrate". Journal of Inorganic and Nuclear Chemistry. 31 (9): 2958–2962. doi:10.1016/0022-1902(69)80218-6.
  23. ^ Iyer, R.Krishna; Deshpande, S.G.; Rao, G.S. (November 1972). "Studies on complexes of tartaric acid—I". Journal of Inorganic and Nuclear Chemistry. 34 (11): 3351–3356. doi:10.1016/0022-1902(72)80229-X.
  24. ^ Kamenar, B.; Grdnić, D.; Prout, C. K. (31 March 1970). "The crystal and molecular structure of racemic potassium di-μ-tartrato-diantimonate(III) trihydrate (racemic 'tartar emetic')". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 26 (3): 181–188. doi:10.1107/S0567740870002133. PMID 5467310.
  25. ^ Gress, Mary E.; Jacobson, Robert A. (January 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: 209–217. doi:10.1016/S0020-1693(00)92617-3.
  26. ^ F. P. Dwyer; F. L. Garvan (1960). "Resolution of cis -Dinitrobis(ethylenediamine)cobalt Ion". Resolution of cis‐Dinitrobis(ethylenediamine)cobalt Ion. Inorganic Syntheses. Vol. 6. pp. 195–197. doi:10.1002/9780470132371.ch62. ISBN 978-0-470-13237-1.

Further reading edit

  • Priesner, Claus (1997). "Basilius Valentinus und die Labortechnik um 1600". Berichte zur Wissenschaftsgeschichte. 20 (2–3): 159–172. doi:10.1002/bewi.19970200205. S2CID 170226309.
  • 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. S2CID 186212284.
  • 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): 407–415. Bibcode:1859AnP...184..407S. doi:10.1002/andp.18591841104.
  • Groschuff, E. (1918). "Reines Antimon". Zeitschrift für anorganische und allgemeine Chemie. 103: 164–188. doi:10.1002/zaac.19181030109.
  • Soubeiran, E.; Capitaine, H. (1840). "Zur Geschichte der Weinsteinsäure". Journal für Praktische Chemie. 19: 435–442. 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): 169–174. doi:10.1002/ardp.18380640215. S2CID 84920753.
  • Zimmermann, E. (1930). "Das Antimon in der Chemotherapie". Klinische Wochenschrift. 9: 27–31. doi:10.1007/BF01740712. S2CID 43264526.
  • 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: 209–217. doi:10.1016/S0020-1693(00)92617-3.

November 23, 2023
antimony, potassium, tartrate, also, known, potassium, antimonyl, tartrate, potassium, antimontarterate, tartar, emetic, formula, k2sb2, c4h2o6, compound, long, been, known, powerful, emetic, used, treatment, schistosomiasis, leishmaniasis, used, resolving, ag. Antimony potassium tartrate also known as potassium antimonyl tartrate potassium antimontarterate or tartar emetic 3 has the formula K2Sb2 C4H2O6 2 The compound has long been known as a powerful emetic and was used in the treatment of schistosomiasis and leishmaniasis It is used as a resolving agent It typically is obtained as a hydrate Antimony potassium tartrate trihydrate Ball and stick model of the bis m2 tartrato di antimony anion 1 2 Sb2 C4H2O6 2 2 Carbon Hydrogen Oxygen AntimonyNamesOther names potassium antimonyl tartrateemetic tartartartar emeticIdentifiersCAS Number 28300 74 5 Y3D model JSmol Interactive imageChEBI CHEBI 2761ChemSpider 17214979ECHA InfoCard 100 116 333EC Number 234 293 3Gmelin Reference 1332600KEGG C11340PubChem CID 16682736UNII DL6OZ476V3 YCompTox Dashboard EPA DTXSID3039240InChI 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 4Key WBTCZEPSIIFINA UHFFFAOYSA JSMILES K K O O O O C1O Sb 23OC1C1O Sb 4 OC C O2 C O O3 C O O4 OC1 OPropertiesChemical formula K2Sb2 C4H2O6 2 3 H2OMolar mass 667 87 g molAppearance white crystalline powderDensity 2 6 g cm3Solubility in water 8 3 g 100 mL 0 C 35 9 g 100 mL 100 C HazardsGHS labelling PictogramsSignal word WarningLethal dose or concentration LD LC LD50 median dose 110 mg kgExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Medical 1 1 Emetic 2 Preparation structure reactions 3 Further reading 4 References 5 Further readingMedical editThe first treatment application against trypanosomiasis was tested in 1906 and the compound s use to treat other tropical diseases was researched 4 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 4 5 After British physician John Brian Christopherson s discovery in 1918 that antimony potassium tartrate could cure schistosomiasis the antimonial drugs became widely used 6 7 8 However the injection of antimony potassium tartrate had severe side effects such as Adams Stokes syndrome 9 and therefore alternative substances were under investigation With the introduction and subsequent larger use of praziquantel in the 1970s antimony based treatments fell out of use 10 11 Tartar emetic was used in the late 19th and early 20th century in patent medicine as a 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 12 13 The New England Journal of Medicine reported 14 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 use disorder 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 intensive care unit 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 Emetic edit nbsp 500 mg tartar emeticAntimony potassium tartrate s potential as an emetic has been 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 15 16 17 The compound is still used to induce vomiting in captured animals in order to study their diets 18 19 20 Preparation structure reactions editAntimony potassium tartrate is prepared by treating a solution of potassium hydrogen tartrate and antimony trioxide 2 KOH Sb2O3 HOCHCO2H 2 K2Sb2 C4H2O6 2 3 H2OWith an excess of tartaric acid the monoanionic monoantimony salt is produced 2 2 KOH Sb2O3 4 HOCHCO2H 2 2 KSb C4H2O6 2 2 H2OAntimony potassium tartrate has been the subject of several X ray crystallography studies 21 22 23 24 25 2 The core complex is an anionic dimer of antimony tartrate Sb2 C4H2O6 22 which is arranged in a large ring with the carbonyl groups pointing outwards The complex has D2 molecular symmetry with two Sb III centers bonded in distorted square pyramids Water and potassium ions are held within the unit cell but are not tightly bound to the dimer The anion is a well used resolving agent 26 nbsp Viewed along the x axis nbsp Viewed along the y axis nbsp Viewed along the z axisFurther reading editOf historic interest Frederick George Mann 1952 Practical organic chemistry England Longmans Green amp Co p 115 ISBN 0 582 44407 1 Knapp Fr 1839 Zur Bildungsgeschichte des Brechweinsteins Annalen der Pharmacie 32 76 85 doi 10 1002 jlac 18390320107 References edit Palenik R C Abboud K A Palenik G J 2005 CSD Entry DKSBTR02 Di potassium bis m2 tartrato di antimony trihydrate Cambridge Structural Database Access Structures Cambridge Crystallographic Data Centre doi 10 5517 cc89ghh a b c Palenik Ruth C Abboud Khalil A Palenik Gus J March 2005 Bond valence sums and structural studies of antimony complexes containing Sb bonded only to O ligands Inorganica Chimica Acta 358 4 1034 1040 doi 10 1016 j ica 2004 11 013 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 PMID 10951203 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 42 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 325 327 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 S2CID 44279233 Publishers Bentham Science October 1996 The Antimonials Current Medicinal Chemistry pp 304 305 Silverman Matt 2003 Loony lawsuits Barnes amp Noble Books p 81 ISBN 978 0 7607 3893 1 Retrieved 1 January 2013 United States v 111 4 DOZEN PACKAGES ETC Retrieved 1 January 2013 Macias 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 68 doi 10 1056 NEJMcpc1111580 PMID 22808962 McCallum RI 1977 President s address Observations upon antimony Proceedings of the Royal Society of Medicine 70 11 756 63 doi 10 1177 003591577707001103 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 doi 10 1177 003591572601901707 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 Grdenic D Kamenar B 1 August 1965 Structures involving unshared electron pairs coordination of antimony in racemic potassium antimonyl tartrate Acta Crystallographica 19 2 197 199 doi 10 1107 S0365110X65003080 Banerjee A K Chari K V R September 1969 Structure of potassium antimony tartrate Journal of Inorganic and Nuclear Chemistry 31 9 2958 2962 doi 10 1016 0022 1902 69 80218 6 Iyer R Krishna Deshpande S G Rao G S November 1972 Studies on complexes of tartaric acid I Journal of Inorganic and Nuclear Chemistry 34 11 3351 3356 doi 10 1016 0022 1902 72 80229 X Kamenar B Grdnic D Prout C K 31 March 1970 The crystal and molecular structure of racemic potassium di m tartrato diantimonate III trihydrate racemic tartar emetic Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry 26 3 181 188 doi 10 1107 S0567740870002133 PMID 5467310 Gress Mary E Jacobson Robert A January 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 8 209 217 doi 10 1016 S0020 1693 00 92617 3 F P Dwyer F L Garvan 1960 Resolution of cis Dinitrobis ethylenediamine cobalt Ion Resolution ofcis Dinitrobis ethylenediamine cobalt Ion Inorganic Syntheses Vol 6 pp 195 197 doi 10 1002 9780470132371 ch62 ISBN 978 0 470 13237 1 Further reading editPriesner Claus 1997 Basilius Valentinus und die Labortechnik um 1600 Berichte zur Wissenschaftsgeschichte 20 2 3 159 172 doi 10 1002 bewi 19970200205 S2CID 170226309 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 S2CID 186212284 Berzelius Jons 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 11 407 415 Bibcode 1859AnP 184 407S doi 10 1002 andp 18591841104 Groschuff E 1918 Reines Antimon Zeitschrift fur anorganische und allgemeine Chemie 103 164 188 doi 10 1002 zaac 19181030109 Soubeiran E Capitaine H 1840 Zur Geschichte der Weinsteinsaure Journal fur Praktische Chemie 19 435 442 doi 10 1002 prac 18400190171 Pfaff C H 1838 Ueber Antimon Wasserstoffgas und die davon abhangige Unsicherheit des von James Marsh entdeckten Verfahrens zur Entdeckung des Arseniks Archiv der Pharmazie 64 2 169 174 doi 10 1002 ardp 18380640215 S2CID 84920753 Zimmermann E 1930 Das Antimon in der Chemotherapie Klinische Wochenschrift 9 27 31 doi 10 1007 BF01740712 S2CID 43264526 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 8 209 217 doi 10 1016 S0020 1693 00 92617 3 Retrieved from https en 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