Antimony potassium tartrate, also known as potassium antimonyl tartrate, potassium antimontarterate, or tartar emetic, has the formula K
2Sb
2(C
4H
2O
6)
2. The compound has long been known as a powerful
emetic
Vomiting (also known as emesis and throwing up) is the involuntary, forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose.
Vomiting can be the result of ailments like food poisoning, gastroenteritis ...
, and was used in the treatment of
schistosomiasis and
leishmaniasis. It is used as a
resolving agent. It typically is obtained as a
hydrate.
Medical
The first treatment application against
trypanosomiasis
Trypanosomiasis or trypanosomosis is the name of several diseases in vertebrates caused by parasitic protozoan trypanosomes of the genus ''Trypanosoma''. In humans this includes African trypanosomiasis and Chagas disease. A number of other diseas ...
was tested in 1906, and the compound's use to treat other tropical diseases was researched.
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
Meglumine antimoniate is a medicine used to treat leishmaniasis. This includes visceral, mucocutaneous, and cutaneous leishmaniasis. It is given by injection into a muscle or into the area infected.
Side effects include loss of appetite, nausea ...
, the use of antimony potassium tartrate was phased out.
After
British
British may refer to:
Peoples, culture, and language
* British people, nationals or natives of the United Kingdom, British Overseas Territories, and Crown Dependencies.
** Britishness, the British identity and common culture
* British English, ...
physician
A physician (American English), medical practitioner (Commonwealth English), medical doctor, or simply doctor, is a health professional who practices medicine, which is concerned with promoting, maintaining or restoring health through th ...
John Brian Christopherson's discovery in 1918 that antimony potassium tartrate could cure schistosomiasis, the antimonial drugs became widely used. However, the injection of antimony potassium tartrate had severe side effects such as
Adams–Stokes syndrome
Stokes–Adams syndrome or Adams–Stokes syndrome is a periodic fainting spell in which there is intermittent complete heart block or other high-grade arrhythmia that results in loss of spontaneous circulation and inadequate blood flow to the bra ...
and therefore alternative substances were under investigation. With the introduction and subsequent larger use of
praziquantel
Praziquantel (PZQ), sold under the brandname Biltricide among others, is a medication used to treat a number of types of parasitic worm infections in mammals, birds, amphibians, reptiles, and fish. In humans specifically, it is used to treat sc ...
in the 1970s, antimony-based treatments fell out of use.
Tartar emetic was used in the late 19th and early 20th century in
patent medicine
A patent medicine, sometimes called a proprietary medicine, is an over-the-counter (nonprescription) medicine or medicinal preparation that is typically protected and advertised by a trademark and trade name (and sometimes a patent) and claimed ...
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.''
The ''New England Journal of Medicine'' 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 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
220px, Intensive care unit
An intensive care unit (ICU), also known as an intensive therapy unit or intensive treatment unit (ITU) or critical care unit (CCU), is a special department of a hospital or health care facility that provides intensi ...
, he experienced severe chest pains, cardiac abnormalities, renal and hepatic toxicity, and nearly died. The Journal reports that "Two years later, he
he patientreports complete abstinence from alcohol."
Emetic
![Brechweinstein](https://upload.wikimedia.org/wikipedia/commons/f/fc/Brechweinstein.jpg)
Antimony potassium tartrate's potential as an emetic was known since the
Middle Ages
In the history of Europe, the Middle Ages or medieval period lasted approximately from the late 5th to the late 15th centuries, similar to the post-classical period of global history. It began with the fall of the Western Roman Empire ...
. 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.
The compound is still used to induce vomiting in captured animals in order to study their diets.
Preparation, structure, reactions
Antimony potassium tartrate is prepared by treating a solution of
potassium hydrogen tartrate and
antimony trioxide:
:2KOH + Sb
2O
3 + (HOCHCO
2H)
2 → K
2Sb
2(C
4H
2O
6)
2 + 3H
2O
With an excess of tartaric acid, the monoanionic monoantimony salt is produced:
:2KOH + Sb
2O
3 + 4(HOCHCO
2H)
2 → 2KSb(C
4H
2O
6)
2 + 2H
2O
Antimony potassium tartrate has been the subject of several
X-ray crystallography
X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...
studies.
The core complex is an anionic dimer of antimony tartrate (Sb
2(C
4H
2O
6)
22-) which is arranged in a large ring with the
carbonyl
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containi ...
groups pointing outwards. The complex has D
2 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.
Further reading
Of historic interest:
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References
Further reading
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{{DEFAULTSORT:Antimony potassium tartrate
Potassium compounds
Antimony(III) compounds
Tartrates
Emetics
Double salts
Drugs with no legal status