(+/-)-THIOPENTAL

(+/-)-THIOPENTAL Basic information
Product Name:(+/-)-THIOPENTAL
Synonyms:5-ETHYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID;5-ETHYL-5-PENTAN-2-YL-2-SULFANYL-1H-PYRIMIDINE-4,6-DIONE;5-Ethyldihydro-5-(1-methylbutyl)-2-thioxo-4,6(1H,5H)-pyrimidinedione;(±)thiopental solution;2-Thio-5-ethyl-5-sec-pentylbarbituric acid;4,6(1H,5H)-Pyrimidinedione, 5-ethyldihydro-5-(1-methylbutyl)-2-thioxo- (9CI);Barbituric acid, 5-ethyl-5-(1-methylbutyl)-2-thio- (8CI);PENTOTHAL ACID
CAS:76-75-5
MF:C11H18N2O2S
MW:242.34
EINECS:200-984-3
Product Categories:Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:76-75-5.mol
(+/-)-THIOPENTAL Structure
(+/-)-THIOPENTAL Chemical Properties
Melting point 158-160°C
density 1.1789 (rough estimate)
refractive index 1.5440 (estimate)
Fp 11℃
storage temp. 2-8°C
solubility ethanol: complete50mg/mL
pka7.11±0.40(Predicted)
form Solid
color White to Off-White
Water Solubility 50mg/L(25 ºC)
CAS DataBase Reference76-75-5(CAS DataBase Reference)
EPA Substance Registry System4,6(1H,5H)-Pyrimidinedione, 5-ethyldihydro-5-(1-methylbutyl)-2-thioxo- (76-75-5)
Safety Information
Hazard Codes Xn,T,F
Risk Statements 22-39/23/24/25-23/24/25-11
Safety Statements 36/37/39-45-36/37-16-7
RIDADR UN 1230 3/PG 2
WGK Germany 3
RTECS CQ6300000
HazardClass 6.1(b)
PackingGroup III
HS Code 2933595960
Hazardous Substances Data76-75-5(Hazardous Substances Data)
Toxicitycyt-hmn:leu 1500 mg/L TGANAK18(1),13,84
MSDS Information
ProviderLanguage
SigmaAldrich English
(+/-)-THIOPENTAL Usage And Synthesis
Chemical PropertiesOff-White Solid
OriginatorPentothal,Abbott
UsesA thio-derivative of Barbituric acid. Controlled substance (depressant). Anesthetic
DefinitionChEBI: Thiopental is a barbiturate, the structure of which is that of 2-thiobarbituric acid substituted at C-5 by ethyl and sec-pentyl groups. It has a role as an anticonvulsant, a sedative, an environmental contaminant, a xenobiotic, a drug allergen and an intravenous anaesthetic. It is functionally related to a 2-thiobarbituric acid. It is a conjugate acid of a thiopental(1-).
Manufacturing Process130 g of ethyl (1-methylbutyl) malonic ester is added to a concentrated solution of sodium ethylate prepared from 34 g of sodium in absolute alcohol; with stirring, 60 g of finely divided thiourea is added, and, the mixture refluxed for 10 hours. Most or all of the solvent is evaporated and the residual mass is dissolved in cold water. The barbituric acid derivative so formed is precipitated by the addition of dilute hydrochloric acid. It may be 1 purified by solution in dilute ammonium hydroxide solution and precipitated by carbon dioxide, followed by recrystallization from 95% alcohol. The ethyl (1- methylbutyl)thiobarbituric acid so obtained is a white crystalline solid, melting at 158-159°C and readily forming salts with alkalies.
Brand nameThiopental is BAN.
Therapeutic FunctionNarcotic analgesic, Anesthetic
Safety ProfilePoison by intraperitoneal, intravenous, and rectal routes. Moderately toxic by ingestion. An experimental teratogen. Human mutation data reported. A short-acting intravenous anesthetic. When heated to decomposition it emits very toxic fumes of NOx and SOx
R(+)-Thioamylal sodium Barbituric acid R-(+)-Thiopental sodium THIOPENTAL ACID Methitural THIOPENTAL, [2-14C] 5-ALLYL-5-[1-METHYLBUTYL]-2-THIOBARBITURIC ACID thialbarbital Thiotetramalum S-Thiopental,S-(-)-Thiopental (+/-)-THIOPENTAL thialbarbital sodium Thiopental Sodium S-(-)-Thiopental sodium Thiopental-d5 (R)-(+)-Thiopental,(R)-Thiopental S(-)-Thioamylal sodium

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