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| Trade names | Valmid, Valamin |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
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| Routes of administration | Oral |
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| Eliminationhalf-life | 2.5 hours |
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| ECHA InfoCard | 100.004.355 |
| Chemical and physical data | |
| Formula | C9H13NO2 |
| Molar mass | 167.208 g·mol−1 |
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Ethinamate, marketed under the brand namesValmid andValamin, is acentral nervous systemdepressant of thecarbamatedrug class. It was formerly prescribed as ahypnotic for the short-term treatment ofinsomnia. The drug has a rapid onset of action, a short elimination half-life of around 2.5 hours, and a correspondingly brief duration of effect. Prolonged use may lead totolerance anddrug dependence, and efficacy typically diminishes after about a week of continuous use.[2]
Ethinamate is no longer available in theNetherlands,Canada,Belarus,Czech Republic, nor theUnited States,[3] having been replaced as an insomnia treatment bybenzodiazepines andZ-drugs.[clarification needed][citation needed]
In the United States, ethinamate is now primarily remembered in connection with the toxicology reports on thedeath of Elvis Presley: it was listed among multiple sedatives detected in his system, and some forensic experts, includingCyril Wecht, later emphasized that polypharmacy was an important factor in the case.[4]
Ethinamate has a broadertherapeutic index than barbiturates, and fatal overdose due to respiratory depression is uncommon.[citation needed] Overdose symptoms includeCNS depression,low blood pressure,shallow breathing,loss of consciousness, and in severe cases, acomatose state. Hypersensitivity reactions may involvethrombocytopenia purpura, fever, and various skin rashes.[3]
Reported cases illustrate that very high doses (15–28 grams) can induce coma, but recovery is possible.[citation needed] Doses up to 1 gram are generally non-fatal, though they may cause prolongedsleep inertia or hangover-like effects. Treatment of overdose focuses on supportive care.Activated charcoal may reduce absorption if administered early (25–100 g for adults; 25–50 g in children under 12; 1 g/kg in infants), andhemodialysis can be considered in severe cases.[citation needed] Respiratory support may be necessary, similar to barbiturate management.
Ethinamate's primary effects result fromCNS depression, manifesting as slow heart rate, shallow breathing, andlow blood pressure. Minor side effects at therapeutic doses include nausea, vomiting, gastrointestinal upset, and skin rash. Rare hypersensitivity reactions may involvethrombocytopenia purpura, fever, and rashes. Children are more likely than adults to experienceparadoxical effects, so the drug was not indicated for individuals under 18.[citation needed]
The drug is classified aspregnancy Category C, and is not recommended during pregnancy or breastfeeding due to insufficient evidence regarding potential teratogenic effects. Animal studies suggest porphyrinogenic potential in vivo.[citation needed]
The compound is synthesized by reactingacetylene withcyclohexanone to form 1-ethynylcyclohexanol. This intermediate is then converted into acarbamate through reaction withphosgene andammonia. Small amounts of lithium or similar reagents may be used to facilitate the initial acetylene reaction.[5][6]
Ethinamate, whosemolecular structure is known as1-ethynylcyclohexanyneone carbamate is an odorless, white crystalline powder. It is typically formulated as 500 mg tablets for oral administration, with an adult dose of one tablet at bedtime; two tablets may be taken if necessary. Children are more prone toparadoxical effects and the drug is not indicated for individuals under 18.[citation needed]The compound is synthesized by reactingacetylene withcyclohexanone to form 1-ethynylcyclohexanol. This intermediate is then converted into acarbamate through reaction withphosgene andammonia. Small amounts of lithium or similar reagents may be used to facilitate the initial acetylene reaction.[5][6]
After ingestion, ethinamate is metabolized to the active compound 4-hydroxyethinamate, which is eliminated in urine with a half-life of approximately 2.5 hours.[2]
