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Chloral hydrate
From Wikipedia, the free encyclopedia
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Chloral hydrate
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| Systematic (IUPAC) name | |
| 2,2,2-trichloroethane-1,1-diol | |
| Identifiers | |
| CAS number | |
| ATC code | N05 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C2H3Cl3O2 |
| Mol. mass | 165.5 g/mol |
| Pharmacokinetic data | |
| Bioavailability | unknown |
| Metabolism | liver, erythrocytes |
| Half life | 7–10 hours in plasma |
| Excretion | bile, feces, urine (various metabolites not unchanged) |
| Therapeutic considerations | |
| Pregnancy cat. |
C |
| Legal status | |
| Routes | Oral capsule/syrup, rectal suppository |
Chloral hydrate, also known as trichloroacetaldehyde monohydrate, 2,2,2-trichloro-1,1-ethanediol, and under the tradenames Aquachloral, Novo-Chlorhydrate, Somnos, Noctec, and Somnote, is a sedative and hypnotic drug as well as a chemical reagent and precursor. Its chemical formula is C2H3Cl3O2.
It is used for the short-term treatment of insomnia and as a sedative before minor medical or dental treatment. It has been largely displaced by the development of benzodiazepines. It was also formerly used as 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 it 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. It is moderately addictive. Chronic use can cause dependency and withdrawal symptoms. It can potentiate various anticoagulants and is weakly mutagenic in vitro and in vivo.
It was discovered through the chlorination of ethanol in 1832 by Justus von Liebig in Gießen. 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 a minor side-product of the chlorination of water; concentrations rarely exceed 5 micrograms per litre (µg/l).
The corresponding anhydrous aldehyde, chloral, is used as an intermediate in insecticide and herbicide manufacture (including DDT, dichlorvos, and naled). Chloral reacts rapidly with water to form chloral hydrate.
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 sometimes lead to its use as a date rape drug.
- Jennie Bosschieter (1882–1900) who was murdered in Paterson, New Jersey on October 19, 1900.
- John Tyndall (1820-1893) died of an accidental overdose.
- Anna Nicole Smith (1967-2007) died of an accidental [1] 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 her drugs would have been sufficient by itself to cause her death.[2].
- Marilyn Monroe had chloral hydrate in her possession and it has been speculated that it contributed to her death.[3]
- 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 shots for the sedative chloral hydrate, which Marshall claimed was a pain reliever.[4].