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Methohexital

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Methohexital
Skeletal formula
Ball-and-stick model
Clinical data
Trade namesBrevital Sodium
Other namesMethohexitone
AHFS/Drugs.comConsumer Drug Information
License data
Routes of
administration		Intravenous,rectal
Drug classBarbiturate
ATC code
Legal status
Legal status
Pharmacokineticdata
BioavailabilityI.V. ~100%
Rectal ~17%
MetabolismLiver
Eliminationhalf-life5.6 ± 2.7 minutes
Excretionexcreted in feces
Identifiers
  • 5-Hex-3-yn-2-yl-1-methyl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.005.272Edit this at Wikidata
Chemical and physical data
FormulaC14H18N2O3
Molar mass262.309g·mol−1
3D model (JSmol)
  • O=C1N(C(=O)NC(=O)C1(C\C=C)C(C#CCC)C)C
  • InChI=1S/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19)checkY
  • Key:NZXKDOXHBHYTKP-UHFFFAOYSA-NcheckY
(verify)

Methohexitalormethohexitone(marketed under the brand namesBrevitalandBrietal) is a drug which is abarbituratederivative. It is classified as short-acting, and has a rapid onset of action.[2]It is similar in its effects tosodium thiopental,a drug with which it competed in the market foranesthetics.

Pharmacology

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Methohexital binds to a distinct site which is associated with Cl−ionophoresat GABAAreceptors.[3]This increases the length of time which the Cl−ionopores are open, thus causing aninhibitoryeffect.

Metabolism of methohexital is primarily hepatic via demethylation and oxidation.[1]Side-chain oxidation is the primary means of metabolism involved in the termination of the drug'sbiological activity.

Indications

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Methohexital is primarily used to induceanesthesia,and is generally provided as a sodium salt (i.e. methohexital sodium). It is only used inhospitalor similar settings, under strict supervision.[1]It has been commonly used to induce deep sedation or general anesthesia for surgery and dental procedures. Unlike many other barbiturates, methohexital actually lowers the seizure threshold, a property that makes it particularly useful when anesthesia is provided for anelectroconvulsive therapy(ECT).[4]Its rapid recovery rate with consciousness being gained within three to seven minutes after induction and full recovery within 30 minutes is a major advantage over other ECT barbiturates.[4]

Synthesis

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Methohexital can be synthesized in the classic manner of making barbituric acid derivatives, in particular by the reaction of malonic ester derivatives with derivatives ofurea.[5]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 withN-methylurea gives methohexital.

Methohexital synthesis

References

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  1. ^abc"Brevital Sodium".DailyMed.July 24, 2019.RetrievedNovember 20,2019.
  2. ^"Methohexital".MeSH.
  3. ^Katzung BG.Basic and Clinical Pharmacology(10th ed.). pp. 406–407.
  4. ^abSchulgasser H, Borowitz AH (August 1963). "Methohexital anaesthesia in electroconvulsive therapy".South African Medical Journal.37:870–1.PMID14045806.
  5. ^US 2872448,Doran WJ, "1,5,5-Trisubstituted barbituric acids", issued February 3, 1959, assigned to Eli Lily and Company(U.S. patent 2,872,448)
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