5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID
![5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID Structure](CAS/GIF/77-27-0.gif)
- CAS No.
- 77-27-0
- Chemical Name:
- 5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID
- Synonyms
- Bio-Tal;Surital;THIAMYLAL;NSC 120815;Thioseconal;Thiamylal RS;ThiaMylal (CIII);Thiamylal sodium salt ;THIAMYLAL, FREE ACID,--DEA SCHEDULE III ITEM;5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID
- CBNumber:
- CB3490680
- Molecular Formula:
- C12H18N2O2S
- Molecular Weight:
- 254.35
- MDL Number:
- MFCD00057565
- MOL File:
- 77-27-0.mol
| 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) |
| FDA UNII | 01T23W89FR |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
|---|---|
| Signal word | Danger |
| Hazard statements | H301+H311+H331 |
| Precautionary statements | P261-P264-P280-P301+P310-P302+P352+P312-P304+P340+P311 |
| 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. |
5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID Chemical Properties,Uses,Production
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