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paraldehyde (n.)
1.a colorless liquid (a cyclic trimer of acetaldehyde) that is used as a sedative and a solvent
Paraldehyde (n.)
1.(MeSH)A hypnotic and sedative with anticonvulsant effects. However, because of the hazards associated with its administration, its tendency to react with plastic, and the risks associated with its deterioration, it has largely been superseded by other agents. It is still occasionally used to control status epilepticus resistant to conventional treatment. (From Martindale, The Extra Pharmacopoeia, 30th ed, p608-9)
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paraldehyde (n.)
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Paraldehyde (n.) [MeSH]
Acetaldehyde, Ethanal[Hyper.]
Paraldehyde (n.)
Paraldehyde Y473[ClasseHyper.]
paraldehyde (n.)
Antiepileptics and antiparkinsonism drugs Y46[àLExclusionDe]
Wikipedia
Paraldehyde | |
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2,4,6-trimethyl-1,3,5-trioxane |
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2,4,6-trimethyl-1,3,5-trioxane |
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Identifiers | |
CAS number | 123-63-7 |
ChemSpider | 21106173 |
UNII | S6M3YBG8QA |
EC number | 204-639-8 |
MeSH | Paraldehyde |
ChEBI | CHEBI:27909 |
ChEMBL | CHEMBL1410743 |
ATC code | N05 |
Jmol-3D images | Image 1 |
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Properties | |
Molecular formula | C6H12O3 |
Molar mass | 132.16 g mol−1 |
Melting point |
12 °C, 285 K, 54 °F ([1]) |
Boiling point |
124 °C, 397 K, 255 °F ([1]) |
Solubility in water | insoluble |
Pharmacology | |
Routes of administration |
Oral/Rectal/Injection |
Legal status |
POM(UK) |
Pregnancy category |
C(US) |
Hazards | |
MSDS | External MSDS |
EU classification | Xn C |
R-phrases | R10 R20 R21 R22 R34 R45 |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
Paraldehyde is the cyclic trimer of acetaldehyde molecules. Formally, it is a derivative of 1,3,5-trioxane. The corresponding tetramer is metaldehyde. A colourless liquid, it is sparingly soluble in water and highly soluble in alcohol. Paraldehyde slowly oxidizes in air, turning brown and producing an odour of acetic acid. It quickly reacts with most plastics and rubber.
Paraldehyde was first synthesized in 1829 by Wildenbusch.[2] It has uses in industry and medicine.
Contents |
Theoretically four stereoisomeric structures are possible. The structures (1) and (2) are known as cis- and trans-paraldehyde. The structures (3) (a conformer of (2)) and (4) (a conformer of (1)) don't exist for steric reasons.[3][4]
Heated with catalytic amounts of acid, it depolymerizes back to acetaldehyde:[5][6]
Since paraldehyde has better handling characteristics, it may be used indirectly or directly as a synthetic equivalent of anhydrous acetaldehyde (b.p. 20 °C). For example, it is used as-is in the synthesis of bromal (tribromoacetaldehyde):[7]
Paraldehyde was introduced into clinical practice in the UK by the Italian physician Vincenzo Cervello in 1882.[2]
It is a CNS depressant and was soon found to be an effective anticonvulsant, hypnotic and sedative. It was included in some cough medicines as an expectorant (though there is no known mechanism for this function beyond the placebo effect).
Paraldehyde was the last injection given to Edith Alice Morrell in 1950 by the suspected serial killer John Bodkin Adams. He was tried for her murder but acquitted.
It was commonly used to induce sleep in sufferers from delirium tremens but has been replaced by other drugs in this regard. It is one of the safest hypnotics and was regularly given at bedtime in psychiatric hospitals and geriatric wards up to the 1960s. Up to 30% of the dose is excreted via the lungs (the rest via the liver). This contributes to a strong unpleasant odour on the breath.
It has been used in the treatment of convulsions.[8]
Today, paraldehyde is sometimes used to treat status epilepticus. Unlike diazepam and other benzodiazepines, it does not suppress breathing at therapeutic doses and so is safer when no resuscitation facilities exist or when the patient's breathing is already compromised.[9] This makes it a useful emergency medication for parents and other caretakers of children with epilepsy. Since the dose margin between the anticonvulsant and hypnotic effect is small, paraldehyde treatment usually results in sleep.
Generic paraldehyde is available in 5ml sealed glass ampoules. Production in the US has been discontinued, but it was previously marketed as Paral.
Paraldehyde has been given orally, rectally, intravenously and by intramuscular injection. It reacts with rubber and plastic which limits the time it may safely be kept in contact with some syringes or tubing before administration.
Paraldehyde is used in resin manufacture, as a preservative, and in other processes as a solvent.
It has been used in the generation of aldehyde fuchsin.[10]
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