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Clomipramine
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Name

Clomipramine

 EINECS 206-144-2
CAS No. 303-49-1 Density 1.119 g/cm3
PSA 6.48000 LogP 4.59340
Solubility 25 mg/mL in water Melting Point 189.5°C
Formula C19H23ClN2 Boiling Point 434.2 °C at 760 mmHg
Molecular Weight 314.858 Flash Point 216.4 °C
Transport Information N/A Appearance white to off-white powder
Safety 36 Risk Codes 20/21/22
Molecular Structure Molecular Structure of 303-49-1 (Clomipramine) Hazard Symbols HarmfulXn
Synonyms

5H-Dibenz[b,f]azepine,3-chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro- (6CI,7CI,8CI);3-Chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine;Chlorimipramine;G 34586;NSC 169865;

Article Data 120

Clomipramine Synthetic route

14171-67-6

clomipramine N-oxide

303-49-1

Clomipramine

Conditions
ConditionsYield
With sodium tetrahydroborate In water at 50 - 60℃; chemoselective reaction;82%
32943-25-2

3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine

53929-74-1

N,N-dimethyl-3-bromopropylamine

303-49-1

Clomipramine

Conditions
ConditionsYield
Stage #1: 3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine With sodium hydride In tetrahydrofuran at 110℃; for 2h; Glovebox; Inert atmosphere; Schlenk technique;
Stage #2: N,N-dimethyl-3-bromopropylamine In tetrahydrofuran at 110℃; for 22h; Glovebox; Inert atmosphere; Schlenk technique;		66%
39607-90-4

3-chloro-5H-dibenzo[b,f]azepine

109-54-6

3-(Dimethylamino)propyl chloride

303-49-1

Clomipramine

Conditions
ConditionsYield
Stage #1: 3-chloro-5H-dibenzo[b,f]azepine With methanol; magnesium at 50℃; for 1.5h;
Stage #2: 3-(Dimethylamino)propyl chloride
106-39-8

bromochlorobenzene

303-49-1

Clomipramine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: caesium carbonate; triphenylphosphine; palladium diacetate; potassium iodide / N,N-dimethyl-formamide / 46 h / 105 °C / Schlenk technique; Inert atmosphere
2: N,N-dimethyl-formamide / 24 h / 130 °C / Schlenk technique; Inert atmosphere
3: magnesium; methanol / 1.5 h / 50 °C
View Scheme
615-36-1

2-bromoaniline

303-49-1

Clomipramine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: caesium carbonate; triphenylphosphine; palladium diacetate; potassium iodide / N,N-dimethyl-formamide / 46 h / 105 °C / Schlenk technique; Inert atmosphere
2: N,N-dimethyl-formamide / 24 h / 130 °C / Schlenk technique; Inert atmosphere
3: magnesium; methanol / 1.5 h / 50 °C
View Scheme
25961-11-9

3-chloro-5-(3-dimethylaminopropyl)-10,11-dihydro-5H-dibenzo(6,5)azepine

303-49-1

Clomipramine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube
2.1: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube
3.1: sodium hydride / tetrahydrofuran / 2 h / 110 °C / Glovebox; Inert atmosphere; Schlenk technique
3.2: 22 h / 110 °C / Glovebox; Inert atmosphere; Schlenk technique
View Scheme

C20H23BClNO2

303-49-1

Clomipramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube
2.1: sodium hydride / tetrahydrofuran / 2 h / 110 °C / Glovebox; Inert atmosphere; Schlenk technique
2.2: 22 h / 110 °C / Glovebox; Inert atmosphere; Schlenk technique
View Scheme
303-49-1

Clomipramine

C19H13(2)H10ClN2

Conditions
ConditionsYield
Stage #1: Clomipramine With hydrogenchloride In 1,4-dioxane; ethyl acetate Inert atmosphere;
Stage #2: With 3,6-bis(dimethylamino)-9-(2,6-dimethylphenyl)-10-methylacridinium bromide; water-d2; lithium carbonate; triisopropylsilanethiol In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Inert atmosphere; Irradiation; regioselective reaction;		98%
10273-89-9

2-(2-methylphenyl)pyridine

303-49-1

Clomipramine

C31H33N3

Conditions
ConditionsYield
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 35℃; for 24h; Inert atmosphere;97%
303-49-1

Clomipramine

C19H21(2)H2ClN2

Conditions
ConditionsYield
Stage #1: Clomipramine With hydrogenchloride In 1,4-dioxane; ethyl acetate Inert atmosphere;
Stage #2: With 9-(4-methoxyphenyl)-10-methylacridinium bromide; water-d2; lithium carbonate; triisopropylsilanethiol In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Inert atmosphere; Irradiation; regioselective reaction;		88%

Clomipramine Chemical Properties

MF:  C19H23ClN2
MW:  314.85
MS:
EINECS: 206-144-2
Mol File: 303-49-1.mol
Solubility  H2O: 25 mg/mL
Form:  powder
color:  white to off-white
Surface Tension: 41.7 dyne/cm 
Density: 1.119 g/cm3 
Flash Point: 216.4 °C 
Enthalpy of Vaporization: 69.03 kJ/mol 
Boiling Point: 434.2 °C at 760 mmHg 
Vapour Pressure: 9.63E-08 mmHg at 25°C  
 

Clomipramine Uses

3-(9-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine hydrochloride (303-49-1 ) have effects on the performance of a variety of causes and symptoms of depression,Obsessive-compulsive disorder,associated with narcolepsy of cataplexy disorder, panic attacks, phobias, chronic pain state and nocturnal enuresis.
 

Clomipramine Toxicity Data With Reference

Organism

Test Type

Route

Reported Dose (Normalized Dose)

Effect

Source

man

TDLo

oral

357ug/kg (0.357mg/kg)

gastrointestinal: nausea or vomiting

Journal of Clinical Pyschopharmacology. Vol. 2, Pg. 215, 1982.

mouse

LD50

intraperitoneal

150mg/kg (150mg/kg)

 

Journal of Medicinal Chemistry. Vol. 21, Pg. 448, 1978.

mouse

LD50

intravenous

27mg/kg (27mg/kg)

 

Acta Pharmaceutica Suecica. Vol. 13, Pg. 485, 1976.

 

mouse

LD50

oral

380mg/kg (380mg/kg)

behavioral: wakefulness

behavioral: changes in motor activity (specific assay)

German Offenlegungsschrift Patent Document. Vol. #2618152,

rat

LD50

intraperitoneal

149mg/kg (149mg/kg)

 

Toxicology. Vol. 24, Pg. 335, 1982.

 

rat

LD50

oral

613mg/kg (613mg/kg)

 

Toxicology. Vol. 24, Pg. 335, 1982.

 

women

TDLo

intravenous

3400ug/kg/47M (3.4mg/kg)

behavioral: convulsions or effect on seizure threshold

cardiac: cardiomyopathy including infarction

British Medical Journal. Vol. 3, Pg. 698, 1972.

women

TDLo

oral

10mg/kg/5D-I (10mg/kg)

vascular: bp elevation not characterized in autonomic section

British Medical Journal. Vol. 1, Pg. 406, 1971.

women

TDLo

oral

30mg/kg (30mg/kg)

behavioral: coma

gastrointestinal: changes in structure or function of endocrine pancreas

gastrointestinal: decreased motility or constipation

Journal of Toxicology, Clinical Toxicology. Vol. 32, Pg. 425, 1994

Clomipramine Safety Profile

Hazard Codes : Xn
Risk Statements:  20/21/22
20/21/22 : 3-(9-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine hydrochloride (303-49-1 ) is harmful by inhalation, in contact with skin and if swallowed .
Safety Statements : 36
36: Keep away from sources of ignition - No smoking
WGK Germany:  3
RTECS:  HN9055000
 
 

Clomipramine Specification

IUPAC Name: 3-(9-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine hydrochloride (303-49-1 )
CAS: 303-49-1
Synonyms: 3-(3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine ; 3-Chloro-5-(3-(dimethylamino)propyl)-10,11-dihydro-5H-dibenz(b,f)azepine ; 3-Chloroimipramine ; 5H-Dibenz(b,f)azepine, 10,11-dihydro-3-chloro-5-(3-(dimethylamino)propyl)- ; 5H-Dibenz[b,f]azepine, 3-chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro- ; 5H-Dibenz[b,f]azepine-5-propanamine, 3-chloro-10,11-dihydro-N,N-dimethyl- ; Anafranil (free base) ; Anafranil base
 

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