Ball-and-stick model of the bis(μ2-tartrato)-di-antimony anion, [1] [2] [Sb2(C4H2O6)2]2− Carbon Hydrogen Oxygen Antimony | |
Names | |
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Other names potassium antimonyl tartrate emetic tartar tartar emetic | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.116.333 |
EC Number |
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1332600 | |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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): | |
LD50 (median dose) | 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 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.
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."
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]
Poisoning by "tartarised antimony" or "emetic tartar" is a plot device in the first modern detective novel, The Notting Hill Mystery (1862). The emetic tartar was kept by a character in the novel because he was "addicted to the pleasures of the table, and was in the habit of taking an occasional emetic." [18]
The compound is still used to induce vomiting in captured animals in order to study their diets. [19] [20] [21]
Antimony potassium tartrate is used as an insecticide against thrips. [22] It is in IRAC class 8E. [23]
Antimony potassium tartrate is prepared by treating a solution of potassium hydrogen tartrate and antimony trioxide:
With an excess of tartaric acid, the monoanionic monoantimony salt is produced: [2]
Antimony potassium tartrate has been the subject of several X-ray crystallography studies. [24] [25] [26] [27] [28] [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. [29]
Of historic interest:
Antimony is a chemical element; it has symbol Sb (from Latin stibium) and atomic number 51. A lustrous grey metal or metalloid, it is found in nature mainly as the sulfide mineral stibnite (Sb2S3). Antimony compounds have been known since ancient times and were powdered for use as medicine and cosmetics, often known by the Arabic name kohl. The earliest known description of this metalloid in the West was written in 1540 by Vannoccio Biringuccio.
Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes but also in tamarinds, bananas, avocados, and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. Potassium bitartrate is commonly mixed with sodium bicarbonate and is sold as baking powder used as a leavening agent in food preparation. The acid itself is added to foods as an antioxidant E334 and to impart its distinctive sour taste. Naturally occurring tartaric acid is a useful raw material in organic chemical synthesis. Tartaric acid, an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics and is a dihydroxyl derivative of succinic acid.
Potassium tartrate, dipotassium tartrate or argol has formula K2C4H4O6. It is the potassium salt of tartaric acid. It is often confused with potassium bitartrate, also known as cream of tartar. As a food additive, it shares the E number E336 with potassium bitartrate.
Succimer, sold under the brand name Chemet among others, is a medication used to treat lead, mercury, and arsenic poisoning. When radiolabeled with technetium-99m, it is used in many types of diagnostic testing. A full course of Succimer lasts for 19 days of oral administration. A second course should be given when more than two weeks pass after the first course.
Antimony oxychloride, known since the 15th century, has been known by a plethora of alchemical names. Since the compound functions as both an emetic and a laxative, it was originally used as a purgative.
An antimonial cup was a small half-pint mug or cup cast in antimony popular in Europe during the 17th and 18th centuries. They were also known under the names "pocula emetica," "calices vomitorii," or "emetic cups", as wine that was kept in one for a 24‑hour period gained an emetic or laxative quality. The tartaric acid in the wine acted upon the metal cup and formed tartarised antimony.
Sodium dimethyldithiocarbamate is the organosulfur compound with the formula NaS2NN(CH3)2. It is one of the simplest organic dithiocarbamates. It is a white or pale yellow, water soluble solid. The compound is a precursor to fungicides and rubber chemicals.
Croconic acid is a chemical compound with formula C5H2O5 or (C=O)3(COH)2. It has a cyclopentene backbone with two hydroxyl groups adjacent to the double bond and three ketone groups on the remaining carbon atoms. It is sensitive to light, soluble in water and ethanol and forms yellow crystals that decompose at 212 °C.
Cyanometallates or cyanometalates are a class of coordination compounds, most often consisting only of cyanide ligands. Most are anions. Cyanide is a highly basic and small ligand, hence it readily saturates the coordination sphere of metal ions. The resulting cyanometallate anions are often used as building blocks for more complex structures called coordination polymers, the best known example of which is Prussian blue, a common dyestuff.
John Brian Christopherson CBE, was a British physician and a pioneer of chemotherapy.
Hexaphenylcarbodiphosphorane is the organophosphorus compound with the formula C(PPh3)2 (where Ph = C6H5). It is a yellow, moisture-sensitive solid. The compound is classified as an ylide and as such carries significant negative charge on carbon. It is isoelectronic with bis(triphenylphosphine)iminium. The P-C-P angle is 131°. The compound has attracted attention as an unusual ligand in organometallic chemistry.
Potassium telluride is an inorganic compound with a chemical formula K2Te. It is formed from potassium and tellurium, making it a telluride. Potassium telluride is a white powder. Like rubidium telluride and caesium telluride, it can be used as an ultraviolet detector in space. Its crystal structure is similar to other tellurides, which have an anti-fluorite structure.
A chloride sulfite or sulfite chloride is a chemical compound that contains chloride and sulfite anions (SO32− Cl−). The known compounds of this type are all late transition metal sulfito complexes. Chlorine may be present as a ligand (chloro) or as an ion (chloride). The sulfito ligand can connect to the metal atom by way of an oxygen, or a sulfur atom. It can also link to the metal atom using two oxygen atoms as a bidentate ligand.
In chemistry, a transition metal chloride complex is a coordination complex that consists of a transition metal coordinated to one or more chloride ligand. The class of complexes is extensive.
Nitratoauric acid, hydrogen tetranitratoaurate, or simply called gold(III) nitrate is a crystalline gold compound that forms the trihydrate, HAu(NO3)4·3H2O or more correctly H5O2Au(NO3)4·H2O. This compound is an intermediate in the process of extracting gold. In older literature it is also known as aurinitric acid.
Titanium(IV) acetate or titanium tetraacetate is a coordination complex and green chloroform soluble solid with the formula Ti(C2H3O2)4. Crystallographic evidence has not been presented. It can be prepared by reacting tetramethyltitanium with acetic acid.
A nitrate nitrite, or nitrite nitrate, is a coordination complex or other chemical compound that contains both nitrite and nitrate anions. They are mixed-anion compounds, and they are mixed-valence compounds. Some have third anions. Many nitrite nitrate compounds are coordination complexes of cobalt. Such a substance was discovered by Wolcott Gibbs and Frederick Genth in 1857.
An iodide nitride is a mixed anion compound containing both iodide (I−) and nitride ions (N3−). Another name is metalloiodonitrides. They are a subclass of halide nitrides or pnictide halides. Some different kinds include ionic alkali or alkaline earth salts, small clusters where metal atoms surround a nitrogen atom, layered group 4 element 2-dimensional structures, and transition metal nitrido complexes counter-balanced with iodide ions. There is also a family with rare earth elements and nitrogen and sulfur in a cluster.
Holmium acetate is the acetate salt of holmium, with a chemical formula of Ho(CH3COO)3 as well as at least one hydrate.
Bromoantimonates are compounds containing anions composed of bromide (Br−) and antimony (Sb). They can be considered as double bromides, metallohalides or halometallates. They are in the category of halopnictates. Related compounds include the bromobismuthates, iodoantimonates, bromophosphates, and bromoarsenates.