5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID
5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID Basic information
- Product Name:
- 5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID
- Synonyms:
-
- THIAMYLAL
- 5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID
- 4,6(1H,5H)-Pyrimidinedione, dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-
- 5-Allyl-5-(1-methylbutyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
- Barbituric acid, 5-allyl-5-(1-methylbutyl)-2-thio-
- Surital
- Thioseconal
- THIAMYLAL, FREE ACID,--DEA SCHEDULE III ITEM
- CAS:
- 77-27-0
- MF:
- C12H18N2O2S
- MW:
- 254.35
- EINECS:
- 201-018-3
- Product Categories:
-
- Heterocycles
- Intermediates & Fine Chemicals
- Neurochemicals
- Pharmaceuticals
- Sulfur & Selenium Compounds
- Mol File:
- 77-27-0.mol
5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID Chemical Properties
- Melting point:
- 132-133°
- Density
- 1.1828 (rough estimate)
- refractive index
- 1.5510 (estimate)
- pka
- 7.01±0.40(Predicted)
- Water Solubility
- 1.298g/L(25 ºC)
Safety Information
- Hazard Codes
- T
- Risk Statements
- 23/24/25
- Safety Statements
- 36/37/39-45
- RIDADR
- 3249
- WGK Germany
- 3
- HazardClass
- 6.1(b)
- PackingGroup
- III
- Toxicity
- An ultra-short-acting barbiturate anesthetic that is used in conjunction with inhalational anesthetics. It acts on the barbiturate-binding site in the GABA receptor complex. Excessive doses cause respiratory depression, apnea, or hypotension. Therapy includes establishing and maintaining airway, supporting the circulation, and administering oxygen.
MSDS
- Language:English Provider:SigmaAldrich
5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID Usage And Synthesis
Description
Thiamylal, 5-allyl-5-(1- methylbutyl)-2-thiobarbituric acid, The sodium salt , Mr 276.36, is an amorphous powder soluble in water. It is prepared by condensation of thiourea with a malonic ester , .
Originator
Surital,Parke Davis,US,1951
Uses
Thiamylal is a barbiturate derivative with sedative, anticonvulsant and hypnotic effects. Thiamylal is used for induction in surgical anaesthesia as well as an anticonvulsant to counteract side effects from other anaesthetics. Thiamylal is a Controlled Substance.
Definition
ChEBI: A member of the class of barbiturates that is 2-thioxodihydropyrimidine-4,6(1H,5H)-dione substituted by a pentan-2-yl and prop-2-en-1-yl group at position 5.
Manufacturing Process
In 450 cc of methanol is added 47 grams of sodium metal and the mixture
allowed to completely react to form a methanol solution of sodium methoxide.
The methanol solution of sodium methoxide is then cooled to 60°C and 68
grams of thiourea which has been thoroughly dried is added with stirring until
a uniform solution is formed. Thereafter, 157 grams of diethyl allyl-(1-
methylbutyl)malonate is added to the solution of the sodio derivative of
thiourea at a temperature of 55°C and the condensation reaction mixture
maintained at the said temperature for 24 hours. Methyl alcohol is removed
under vacuum during the course of the reaction while maintaining a
temperature of 55°C.
The viscous reaction mixture is then poured into 1.5 liters of ice water and
agitated to form a uniform solution. The solution is treated with activated
carbon and filtered. Thereafter, 80% acetic acid is added until the filtered
solution remains acidic to litmus. The precipitate formed is filtered and
washed thoroughly with distilled water. The product is air-dried at a temperature of 95° to 100°C for 48 hours to yield 133 grams of 5-allyl-5-(1-
methylbutyl)-2-thiobarbituric acid having a melting point of 132° to 133°C
and assaying at 99.5% pure, from US Patent 2,876,225.
Therapeutic Function
Anesthetic