5-(hex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

• ChemBase ID: 357
• Molecular Formular: C14H18N2O3
• Molecular Mass: 262.30432
• Monoisotopic Mass: 262.13174245
• SMILES: O=C1N(C(=O)NC(=O)C1(C(C)C#CCC)CC=C)C
• Canonical SMILES: CCC#CC(C1(CC=C)C(=O)NC(=O)N(C1=O)C)C
• InChI: 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)
• InChIKey: NZXKDOXHBHYTKP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(hex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: methohexital sodium; methohexital
• Brand Name: Brevital; Brevital sodium; Brietal
• Synonyms: Methodrexitone; Methohexitone; Methohexital; 1-Methyl-5-(1-methyl-2-pentyn-1-yl)-5-(2-propen-1-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbituric Acid; Brevital; Brietal; Compound 22451; Compound 25398; Enallynymall

Database IDs

• CAS Number: 151-83-7
• PubChem SID: 46507954; 160963820
• PubChem CID: 9034
• CHEBI ID: 102216
• ATC CODE: N01AF01; N05CA15
• CHEMBL: 7413
• Chemspider ID: 8683
• DrugBank ID: DB00474
• KEGG ID: D04985
• Unique Ingredient Identifier: E5B8ND5IPE
• Wikipedia Title: Methohexital

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.731305
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.2865314
• LogD (pH = 7.4): 2.2672198
• Log P: 2.2867832
• Molar Refractivity: 71.5071 cm^3
• Polarizability: 26.970406 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.43
• LOG S: -3.7
• Solubility (Water): 5.24e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.8

Pharmacology Properties

• Admin Routes: Intravenous, rectal
• Bioavailability: I.V. ~100%; Rectal ~17%
• Half Life: 5.6 ± 2.7 minutes
• Metabolism: Hepatic
• Legal Status: Schedule IV
• Pregnancy Category: B (USA)

DETAILS

DrugBank - DB00474

• Drug Groups: approved
• Description: An intravenous anesthetic with a short duration of action that may be used for induction of anesthesia. [PubChem]
• Indication: Methohexital is indicated for use as an intravenous anaesthetic. It has also been commonly used to induce deep sedation.
• Pharmacology: Methohexital, a barbiturate, is used for the induction of anesthesia prior to the use of other general anesthetic agents and for induction of anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.
• Toxicity: The onset of toxicity following an overdose of intravenously administered methohexital will be within seconds of the infusion. If methohexital is administered rectally or is ingested, the onset of toxicity may be delayed. The manifestations of an ultrashort-acting barbiturate in overdose include central nervous system depression, respiratory depression, hypotension, loss of peripheral vascular resistance, and muscular hyperactivity ranging from twitching to convulsive-like movements. Other findings may include convulsions and allergic reactions. Following massive exposure to any barbiturate, pulmonary edema, circulatory collapse with loss of peripheral vascular tone, and cardiac arrest may occur.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolism occurs in the liver through demethylation and oxidation. Side-chain oxidation is the most important biotransformation involved in termination of biologic activity.
• Absorption: The absolute bioavailability following rectal administration of methohexital is 17%.
• Half Life: 5.6 ± 2.7 minutes
• Protein Binding: 73%
• Elimination: Excretion occurs via the kidneys through glomerular filtration.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - M260650

Methohexital is a short-acting barbiturate used as a sedative. Methohexital is used an anesthetic for oral surgery and dentistry and is also used to induce anesthesia prior to electroconvulsive therapy (ECT). Methohexital is a Controlled Substance.

REFERENCES

• Avramov, M.N. et al.: Anesth. Analges., 81, 596 (1995)
• Hamid, S.K. et al.: Br. J. Anaesth., 77, 727 (1995)