• Name

  (+/-)-THIOPENTAL

• EINECS
• CAS No. 76-75-5
• Article Data12
• CAS DataBase
• Density 1.16g/cm³
• Solubility 50mg/L(25 oC)
• Melting Point 158-160°C
• Formula C11H18 N2 O2 S
• Boiling Point
• Molecular Weight 242.342
• Flash Point 11℃
• Transport Information
• Appearance Off-White Solid
• Safety Poison 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 NO_x and SO_x. See also PENTOTHAL SODIUM and BARBITURATES.
• Risk Codes 22-39/23/24/25-23/24/25-11
• Molecular Structure
• Hazard Symbols Xn,T,F
• Synonyms Barbituricacid, 5-ethyl-5-(1-methylbutyl)-2-thio- (8CI); (?à)-Thiopental; 2-Thio-5-ethyl-5-sec-pentylbarbituricacid; 5-Ethyl-5-(1-methylbutyl)-2-thiobarbituric acid; Intraval;Penthiobarbital; Pentothiobarbital; Thiomebumal; Thionembutal; Thiopental;Thiopentobarbital; Thiopentobarbitone; Thiopentobarbituric acid; Thiopentone;Thiothal
• PSA 90.29000
• LogP 2.00750

Synthetic route

57-33-0

nembutal

76-75-5

thiopentone

Conditions

Conditions	Yield
Stage #1: nembutal With hydrogenchloride In dichloromethane at 20℃; for 0.166667h; Stage #2: With Lawessons reagent; methoxybenzene for 150h; Reflux;	20%

91334-59-7

5-ethyl-6-amino-5-(1-methyl-butyl)-2-thioxo-3,5-dihydro-2H-pyrimidin-4-one

76-75-5

thiopentone

Conditions

Conditions	Yield
With sulfuric acid
With sulfuric acid

76-74-4

pentobarbital

A

76-75-5

thiopentone

B

134302-74-2

5-ethyl-5-(1-methylbutyl)-2,4-dithiobarbitursaeure

Conditions

Conditions	Yield
With P4S10*4Py In chlorobenzene for 1h; Heating; Yield given. Yields of byproduct given;

(+-)-5-ethyl-5-<1-methyl-butyl>-barbituric acid

(+-)-5-ethyl-5-<1-methyl-butyl>-barbituric acid

76-75-5

thiopentone

Conditions

Conditions	Yield
With tetraphosphorus decasulfide; potassium polysulfide; xylene

17356-08-0

thiourea

(+-)-ethyl-<1-methyl-butyl>-malonic acid diethyl ester

(+-)-ethyl-<1-methyl-butyl>-malonic acid diethyl ester

76-75-5

thiopentone

Conditions

Conditions	Yield
With sodium ethanolate

107-81-3

2-bromopentane

76-75-5

thiopentone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium ethylate; ethanol 3: aqueous H2SO4 View Scheme
Multi-step reaction with 4 steps 1: sodium ethylate; ethanol 2: sodium ethylate; ethanol 4: aqueous H2SO4 View Scheme

100400-64-4

2-ethyl-2-cyano-3-methyl-hexanoic acid methyl ester

76-75-5

thiopentone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: aqueous H2SO4 View Scheme

19823-28-0

2-cyano-3-methyl-hexanoic acid ethyl ester

76-75-5

thiopentone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium ethylate; ethanol 3: aqueous H2SO4 View Scheme

100453-11-0

2-ethyl-2-cyano-3-methyl-hexanoic acid ethyl ester

76-75-5

thiopentone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: aqueous H2SO4 View Scheme

1619-58-5

2-cyano-butyric acid ethyl ester

76-75-5

thiopentone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium ethylate; ethanol 3: aqueous H2SO4 View Scheme

76-75-5

thiopentone

104-94-9

4-methoxy-aniline

107235-67-6

5-Ethyl-2-(4-methoxy-phenylimino)-5-(1-methyl-butyl)-dihydro-pyrimidine-4,6-dione

Conditions

Conditions	Yield
at 160 - 180℃;	83%

76-75-5

thiopentone

106-49-0

p-toluidine

107235-65-4

5-Ethyl-5-(1-methyl-butyl)-2-p-tolylimino-dihydro-pyrimidine-4,6-dione

Conditions

Conditions	Yield
at 160 - 180℃;	75%

76-75-5

thiopentone

90-04-0

2-methoxy-phenylamine

107235-68-7

5-Ethyl-2-(2-methoxy-phenylimino)-5-(1-methyl-butyl)-dihydro-pyrimidine-4,6-dione

Conditions

Conditions	Yield
at 160 - 180℃;	67%

76-75-5

thiopentone

108-44-1

1-amino-3-methylbenzene

107235-66-5

5-Ethyl-5-(1-methyl-butyl)-2-m-tolylimino-dihydro-pyrimidine-4,6-dione

Conditions

Conditions	Yield
at 160 - 180℃;	67%

76-75-5

thiopentone

62-53-3

aniline

107235-64-3

5-Ethyl-5-(1-methyl-butyl)-2-phenylimino-dihydro-pyrimidine-4,6-dione

Conditions

Conditions	Yield
at 160 - 180℃;	56%

76-75-5

thiopentone

5-ethyl-2-(1-methyl-butylmercapto)-1H-pyrimidine-4,6-dione

Conditions

Conditions	Yield
With sulfuric acid

76-75-5

thiopentone

10016-20-3

alpha cyclodextrin

C36H60O30*C11H18N2O2S

Conditions

Conditions	Yield
In water complex stability constant; pH 5;

76-75-5

thiopentone

10016-20-3

alpha cyclodextrin

C42H70O35*C11H18N2O2S

Conditions

Conditions	Yield
In water complex stability constant; pH 5;

PENTOTHAL Chemical Properties

MF: C₁₁H₁₈N₂O₂S
MW: 242.34
EINECS: 200-984-3
PENTOTHAL,it's melting point is  158-160°C,It's appearance is Off-White Solid.
Following is the molecular structure of PENTOTHAL:

PENTOTHAL Toxicity Data With Reference

PENTOTHAL Safety Profile