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| CAS No.: | 303-49-1 |
|---|---|
| Name: | Clomipramine |
| Article Data: | 120 |
| Molecular Structure: | |
|
|
|
| Formula: | C19H23ClN2 |
| Molecular Weight: | 314.858 |
| 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; |
| EINECS: | 206-144-2 |
| Density: | 1.119 g/cm3 |
| Melting Point: | 189.5°C |
| Boiling Point: | 434.2 °C at 760 mmHg |
| Flash Point: | 216.4 °C |
| Solubility: | 25 mg/mL in water |
| Appearance: | white to off-white powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 20/21/22 |
| Safety: | 36 |
| PSA: | 6.48000 |
| LogP: | 4.59340 |
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clomipramine N-oxide
- 303-49-1
Clomipramine
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| Stage #1: 3-chloro-5H-dibenzo[b,f]azepine With methanol; magnesium at 50℃; for 1.5h; Stage #2: 3-(Dimethylamino)propyl chloride |
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 |
- 303-49-1
Clomipramine
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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% |
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Chemistry
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
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.
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 | 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 | 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 | Journal of Toxicology, Clinical Toxicology. Vol. 32, Pg. 425, 1994 |
Safety Profile
Hazard Codes : Xn .gif){kind=small}
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
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