CYCLOBARBITAL Chemical Properties

Melting point:

171-174°

Boiling point:

378.73°C (rough estimate)

Density 

1.1623 (rough estimate)

refractive index 

1.5460 (estimate)

solubility 

Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)

form 

Solid

pka

8.03±0.10(Predicted)

color 

White to Off-White

Water Solubility 

8.27g/L(25 ºC)

Safety Information

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

Toxicity

LD50 in mice, rats (mg/kg): 350, 290 i.p. (Hofrichter)

CYCLOBARBITAL Usage And Synthesis

Originator

Cyclobarbital,Bayer

Uses

Cyclobarbital has been used as an anesthetic and sedative. Controlled substance (depressant).

Definition

ChEBI: Cyclobarbital is a member of barbiturates.

Manufacturing Process

772.0 g of δ-1,2-cyclohexenylcyanacetic acid ethyl ester are introduced into astirred and ice cooled solution of 92.0 g of sodium in 1500 ml of absolutealcohol. The sodium δ-1,2-cyclohexenylcyanacetic acid ester formed is thengradually treated without ice cooling with 750.0 g of ethyl iodide. The reactionmixture become warm, sodium iodide separates out and the whole is neutralafter a short time. The sodium iodide is filtered off, the filtrate freed fromalcohol by distillation, the residues taken up in water, siphoned off, dried overcalcium chloride and distilled in vacuum, yields δ-1,2-cyclohexenylethylcyanacetic acid ethyl ester, boil point 125°C. 72.0 g ofsodium are dissolved in 1086.0 g of absolute alcohol and boiled for 3.75 hwith 285.0 g of guanidine sulfate, then 221.0 g of δ-1,2-cyclohexenylethylcyanacetic acid ester are added and boiling is continued for afurther 12 h. The residue remaining after distilling off the alcohol is boiledwith 10 times its weight of dilute sulfuric acid and then δ-1,2-cyclohexenylethylbarbituric acid which separates out is recrystallized from hotwater, melting point 170°C

brand name

Phanodorn (Sterling Winthrop).

Therapeutic Function

Hypnotic

Safety Profile

Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: pulmonary consolidation. Used as a central nervous system depressant, hypnotic, and sedative. When heated to decomposition it emits toxic fumes of NOx. See also BARBITURATES.

CYCLOBARBITAL(52-31-3)Related Product Information

• 2-(1-CYCLOHEXENYL)ETHYLAMINE
• Hexethal
• CYCLOBARBITAL
• BUTETHAL--DEA SCHEDULE III ITEM
• DIHYDROTHYMINE
• BARBITAL
• vinbarbital
• Cyclohexene
• Barbituric acid
• 5,5-DIMETHYLBARBITURIC ACID
• 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl- (9CI)
• 5-ethylbarbituric acid
• 3-BUTENAMIDE
• Cyclobarbital sodium
• Reposal
• 1-TERT-BUTYL-1-CYCLOHEXENE
• cyclobarbital calcium
• norhexobarbital