| Identification | Back Directory | [Name]
5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID | [CAS]
77-27-0 | [Synonyms]
Surital
Bio-Tal
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
Barbituric acid, 5-allyl-5-(1-methylbutyl)-2-thio-
(+)-5-Allyl-5-[(R)-1-methylbutyl]-2-thiobarbituric acid
Barbituric acid, 5-allyl-5-(1-methylbutyl)-2-thio- (8CI)
5-Allyl-5-(1-methylbutyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
(+)-5-Allyl-5-[(R)-1-methylbutyl]-2-thioxopyrimidine-4,6(1H,3H,5H)-dione
Dihydro-5-(1-Methylbutyl)-5-(2-propenyl)-2-thioxo-4,6(1H,5H)-pyriMidinedione
4,6(1H,5H)-Pyrimidinedione, dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-
Dihydro-5-(1-Methylbutyl)-5-(2-propen-1-yl)-2-thioxo-4,6(1H,5H)-pyriMidinedione
4,6(1H,5H)-Pyrimidinedione, dihydro-5-(1-methylbutyl)-5-(2-propen-1-yl)-2-thioxo-
4,6(1H,5H)-Pyrimidinedione, dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo- (9CI) | [EINECS(EC#)]
201-018-3 | [Molecular Formula]
C12H18N2O2S | [MDL Number]
MFCD00057565 | [MOL File]
77-27-0.mol | [Molecular Weight]
254.35 |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [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. |
| Hazard Information | Back Directory | [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 |
|