Chloral hydrate
From Wikipedia, the free encyclopedia
| Chloral hydrate | |
|---|---|
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| IUPAC name | 2,2,2-trichloroethane-1,1-diol |
| Other names | trichloroacetaldehyde monohydrate Tradenames: Aquachloral, Novo-Chlorhydrate, Somnos, Noctec, Somnote |
| Identifiers | |
| CAS number | [302-17-0] |
| PubChem | |
| SMILES | ClC(Cl)(Cl)C(O)O |
| InChI | 1/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H |
| Properties | |
| Molecular formula | C2H3Cl3O2 |
| Molar mass | 165.403 g/mol |
| Appearance | Colorless solid |
| Density | 1.91 g/cm3 |
| Melting point |
57 °C, 330 K, 135 °F |
| Boiling point |
98 °C, 371 K, 208 °F |
| Pharmacology | |
| Bioavailability | well absorbed |
| Routes of administration |
Oral capsule/syrup, rectal suppository |
| Metabolism | converted to trichloroethanol, hepatic and renal |
| Elimination half-life |
8–10 hours in plasma |
| Excretion | bile, feces, urine (various metabolites not unchanged) |
| Legal status | |
| Pregnancy category |
C(US) |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Harmful (Xn) |
| R-phrases | R22 R36 R37 R38 |
| Related compounds | |
| Related compounds | Chloral, chlorobutanol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Chloral hydrate is a sedative and hypnotic drug as well as a chemical reagent and precursor. The name chloral hydrate indicates that it is formed from chloral (trichloroacetaldehyde) by the addition of one molecule of water. Its chemical formula is C2H3Cl3O2.
It was discovered through the chlorination of ethanol in 1832 by Justus von Liebig in Gießen.[1][2] Its sedative properties were first published in 1869 and subsequently, because of its easy synthesis, its use was widespread.[3] It was widely abused and misprescribed in the late 19th century. Chloral hydrate is soluble in both water and alcohol, readily forming concentrated solutions. A solution of chloral hydrate in alcohol called "knockout drops" was used to prepare a Mickey Finn.
It is, together with chloroform, a minor side-product of the chlorination of water, if organic residues are present in the water, concentrations rarely exceeding 5 micrograms per litre (µg/l).
Contents |
[edit] Production
Chloral hydrate is produced from chlorine and ethanol in acidic solution. In basic conditions the haloform reaction takes place and chloroform is produced.
- 4 Cl2 + C2H5OH + H2O → Cl3CCH(OH)2 + 5 HCl
[edit] Uses
[edit] Synthesis
Chloral hydrate is a cheaply available building block chemical. It is the starting material for the production of chloral, which is produced by the distillation of a mixture of chloral hydrate and sulfuric acid, which serves as the desiccant.
Notably, it is used to synthesize isatin. In this synthesis, chloral hydrate reacts with aniline and hydroxylamine to give a condensation product which cyclicizes in sulfuric acid to give the target compound:[4]
[edit] Sedative
Chloral hydrate is used for the short-term treatment of insomnia and as a sedative before minor medical or dental treatment. It was largely displaced in the mid-20th century by barbiturates[5] and subsequently by benzodiazepines. It was also formerly used in veterinary medicine as a general anesthetic. Today, it is commonly used as an ingredient in the veterinary anesthetic Equithesin.
In therapeutic doses for insomnia chloral hydrate is effective within sixty minutes, it is metabolized within 4 minutes into trichloroethanol by erythrocytes and plasma esterases and many hours later into trichloroacetic acid. Higher doses can depress respiration and blood pressure. An overdose is marked by confusion, convulsions, nausea and vomiting, severe drowsiness, slow and irregular breathing, cardiac arrhythmia and weakness. It may also cause liver damage and is moderately addictive, as chronic use is known to cause dependency and withdrawal symptoms. The chemical can potentiate various anticoagulants and is weakly mutagenic in vitro and in vivo[citation needed].
Chloral hydrate is now illegal in the United States without a prescription. Chloral hydrate is a schedule IV controlled substance in the United States. Its properties have sometimes led to its use as a date rape drug.
[edit] See also
- Jennie Bosschieter (1882–1900) who was murdered in Paterson, New Jersey on October 19, 1900.
- John Tyndall (1820-1893) who died of an accidental overdose.
- Anna Nicole Smith (1967-2007) who died of an accidental[6] combination of chloral hydrate with three benzodiazepines, as announced by forensic pathologist Dr. Joshua Perper on 3/26/07. Chloral hydrate was the major factor, but none of these drugs would have been sufficient by itself to cause her death.[7]
- Marilyn Monroe had chloral hydrate in her possession, and it has been speculated that it contributed to her death.[8]
- Hank Williams came under the spell of a man calling himself "Doctor" Toby Marshall (actually a paroled forger), who often supplied him with prescriptions and injections of chloral hydrate, which Marshall claimed was a pain reliever.[9]
- William S. Burroughs was expelled from school for experimenting with chloral hydrate along with another pupil. The incident is detailed in the writer's foreword to Junkie.
- Mary Todd Lincoln was given chloral hydrate for sleep problems. See Mary Todd Lincoln by Jean Baker and Mary: Mrs. A. Lincoln, by Janis Cooke Newman.
- It was used in the murder-suicides of the People's Temple in Jonestown, Guyana.
[edit] Chloral hydrate in fiction and film
- Bram Stoker, "Dracula," 1897
- Edith Wharton, "The House of Mirth." New York, C. Schribner’s Sons, 1905.
- Evelyn Waugh, Vile Bodies. London, Chapman & Hall Ltd., 1930.
- Margery Allingham, "The Case of the Late Pig." Hodder & Stoughton, 1937.
- Agatha Christie, "And Then There Were None." Dodd, Mead and Company, 1940.
- Rex Stout, "The Final Deduction," Chapter 7. Viking Press, 1961.
- From Russia with Love, Movie, 1963.
- Jimmy Breslin, "The Gang That Couldn't Shoot Straight," 1969.
- Larry Gelbart, "M*A*S*H*" TV-Series, Season 3, 1974.
- The Living Daylights, Movie, 1987.
- Caleb Carr, "The Alienist." Random House, 1994.
- Sarah Waters, Affinity. London: Virago Press, 1999.
- Oz, TV-Series, Multiple episodes,(Handicap used by Ryan O'Rielly)
- David Shore, "House M.D." TV-Series, Season 1, 2004.
- The Venture Brothers, TV-Series, Season 1, Episode 4, 2004
- Taxi Driver, Martin Scorsese, Travis is offered this by gun dealer
- Thomas Pynchon, Against the Day, London, Vintage Books, 2007.
[edit] References
- ^ Justus Liebig (1832). "Ueber die Zersetzung des Alkohols durch Chlor". Annalen der Pharmacie 1 (1): 31-32. doi:.
- ^ Justus Liebig (1832). "Ueber die Verbindungen, welche durch die Einwirkung des Chlors auf Alkohol, Aether, ölbildendes Gas und Essiggeist entstehen". Annalen der Pharmacie 1 (2): 182-230. doi:.
- ^ Liebreich, Oskar (1869). Das Chloralhydrat : ein neues Hypnoticum und Anaestheticum und dessen Anwendung in der Medicin ; eine Arzneimittel-Untersuchung. Müller.
- ^ C. S. Marvel and G. S. Hiers (1941). "Isatin". Org. Synth.; Coll. Vol. 1: 327.
- ^ Tariq, Syed H. and Shailaja Pulisetty; “Pharmacotherapy for Insomnia”, Clinics in Geriatric Medicine (24), 2008 p. 93-105 PMID: 18035234
- ^ Anna Nicole Smith Autopsy Report. XI. Manner of death. A. The Exclusion of Homicide The Smoking Gun
- ^ Anna Nicole Smith Autopsy Released. Coroner: Ex-Playmate died from accidental sedative overdose The Smoking Gun
- ^ Marily Monroe. Theories Crime Library
- ^ Hank Williams summary Book Rags
