5981. Methohexital

Nomenclature

CAS number: 151-83-7
1-Methyl-5-(1-methyl-2-pentyn-1-yl)-5-(2-propen-1-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione; α-dl-5-allyl-1-methyl-5-(1-methyl-2-pentynyl)barbituric acid; α-dl-1-methyl-5-(1-methyl-2-pentynyl)-5-allylbarbituric acid; methohexitone.
C14H18N2O3; mol wt 262.30.
C 64.11%, H 6.92%, N 10.68%, O 18.30%.

Description and references

Barbituric acid hypnotic. Prepn of the α-racemate: W. J. Doran, US 2872448 (1959 to Lilly). Resolution of enantiomers: idem, J. Org. Chem. 25, 1737 (1960). Enantioselective synthesis and activity of isomers: H. Brunner, Chirality 13, 420 (2001); idem et al., Eur. J. Org. Chem. 2003, 855. HPLC determn in plasma: M. J. Avram, T. C. Krejcie, J. Chromatogr. 414, 484 (1986). Clinical pharmacokinetics: Y. Le Normand et al., Br. J. Clin. Pharmacol. 26, 589 (1988). Review of use in dental anesthesia: C. H. Martone et al., Anesth. Prog. 38, 195-199 (1991); in orthopedic procedural sedation: T. Austin et al., J. Emerg. Med. 24, 315-318 (2002).

Chemical structure

Properties

Crystals from dil ethanol as the α-dl-racemate, mp 96°. Very slightly sol in water; slightly sol in ethanol, chloroform, dil alkalies.

Derivative

Sodium salt.

Nomenclature

CAS number: 309-36-4
Brevital (Monarch); Brevimytal (Lilly); Brietal (Lilly).
C14H17N2NaO3; mol wt 284.29.
C 59.15%, H 6.03%, N 9.85%, Na 8.09%, O 16.88%.

Properties

White crystalline powder. Freely soluble in water.

Note

This is a controlled substance (depressant): 21 CFR, 1308.14.

Therapeutic Category

Anesthetic (intravenous).

Therapeutic Category (Veterinary)

Anesthetic (intravenous).

Keywords

Anesthetic (Intravenous)