Methohexital
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Systematic (IUPAC) name | |
5-hex-3-yn-2-yl-1- methyl-5-prop-2-enyl-1, 3-diazinane-2,4,6-trione | |
Clinical data | |
AHFS/Drugs.com | Consumer Drug Information |
Pregnancy cat. | B (USA) |
Legal status | Prescription Only (S4) (AU) Schedule IV |
Routes | Intravenous, rectal |
Pharmacokinetic data | |
Bioavailability | I.V. ~100% Rectal ~17% |
Metabolism | Hepatic |
Half-life | 5.6 ± 2.7 minutes |
Excretion | ? |
Identifiers | |
CAS number | 151-83-7 ![]() |
ATC code | N01AF01 N05CA15 |
PubChem | CID 9034 |
DrugBank | DB00474 |
ChemSpider | 8683 ![]() |
UNII | E5B8ND5IPE ![]() |
KEGG | D04985 ![]() |
ChEBI | CHEBI:102216 ![]() |
ChEMBL | CHEMBL7413 ![]() |
Chemical data | |
Formula | C14H18N2O3 |
Mol. mass | 262.304 |
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Methohexital or methohexitone, (marketed under the brand name Brevital) is a drug which is a barbiturate derivative. It is classified as short-acting, and has a rapid onset of action. It is similar in its effects to sodium thiopental, a drug with which it competed in the market for anaesthetics.
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Pharmacology [edit]
Methohexital binds to a distinct site which is associated with Cl− ionophores at GABAA receptors.[1] This increases the length of time which the Cl− ionopores are open, thus causing an inhibitory effect.
Metabolism of methohexital is primarily hepatic (i.e., taking place in the liver) via demethylation and oxidation.[citation needed] Side-chain oxidation is the primary means of metabolism involved in the termination of the drug's biological activity.
Protein binding is approximately 73% for methohexital.[citation needed]
Indications [edit]
Methohexital is primarily used to induce anesthesia, and is generally provided as a sodium salt (i.e. methohexital sodium). It is only used in hospital or similar settings, under strict supervision.[citation needed] It has been commonly used to induce deep sedation, "twilight sleep" or general anesthesia for oral surgery and dentistry. It is also used to induce anesthesia prior to ECT (electroconvulsive therapy).
Chemistry [edit]
Methohexital, 5-allyl-1-methyl-5-(1-methyl-2-pentinyl barbituric acid, is synthesized in the classic manner of making barbituric acid derivatives, in particular by the reaction of malonic ester derivatives with derivatives of urea. The resulting allyl-(1-methyl-2-pentynyl) malonic ester is synthesized by subsequent alkylation of the malonic ester itself, beginning with 2-bromo-3-hexyne, which gives (1-methyl-2-pentynyl)malonic ester, and then by allylbromide. In the final step, reaction of the disubstituted malonic ester with N-methylurea gives desired methohexital.
W.J. Doran, U.S. Patent 2,872,448 (1959).
References [edit]
- ^ Katzung, Bertram G., Basic and Clinical Pharmacology, 10th ed., p. 406-407
External links [edit]
- RxList.com - Methohexital
- Drugs.com - Methohexital Sodium
- DrugLib.com - Brevital (Methohexital Sodium)
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