HEXOBARBITAL

Description

Hexobarbital is a barbiturate derivative that has sedative and hypnotic effects. It has been marketed under numerous trade names such as Somnalert, Citopan, and Sombulex. In the 1940s and 1950s, hexobarbital was used as an anesthetic for surgery; but, largely because it is difficult to control the depth of the sedation, it has been replaced by safer drugs, notably the barbiturate thiopental.

Description

Hexobarbital, 5-(cyclohexen-1- yl)-1,5-dimethylbarbituric acid,Mr 236.26. The acid forms colorless crystals that turn pink on exposure to light, mp 146 ?C. A 10 % aqueous solution of the sodium salt, Mr 258.25, has a pH of 11.5.

Chemical properties

White crystals.

The Uses of HEXOBARBITAL

Medicine (sedative).

Definition

ChEBI: A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.

brand name

Cyclonal sodium;Cyclopan;Dorico soluble;Eviderm;Evipal sodium;Evipanl;Hexanal;Hexanastab oral.

World Health Organization (WHO)

Hexobarbital is a short-acting barbiturate. See WHO comment for barbiturates.

Clinical Use

Methohexital sodium is a short-acting anesthetic administered intravenously. It is very potent and has the shortest duration of action among the barbiturates used. A disturbing factor is that rather frequently it causes hiccups directly after injection. Patients are reported to recover rapidly from anesthesia. Abuse can lead to addiction.

Synthesis

Hexobarbital sodium is prepared by condensation of methyl(cyclohexen-1-yl)cyanoacetic ester with dicyanodiamide to 5-(cyclohexen- 1-yl)-5-methyl-2,6-diimino-3-cyanobarbituric acid, followed by methylation with dimethyl sulfate and hydrolysis with 25 % sulfuric acid .