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26786-32-3

26786-32-3 Structure

26786-32-3 Structure
IdentificationBack Directory
[Name]

LOFEPRAMINE HYDROCHLORIDE
[CAS]

26786-32-3
[Synonyms]

db-2182
WHR 2908A
WHR-2908A
ropylaminehcl
acetophenonehcl
LOFEPRAMINE HCL
leo640hydrochloride
lopraminehydrochloride
iopraminehydrochloride
LOFEPRAMINE HYDROCHLORIDE
clopepraminehydrochloride
lofepramine hydrochloride (form A)
Lofepramine Hydrochloride DISCONTINUED, UNSTABLE, OFFER L469380
f)azepine,5-(3-((p-chlorobenzoylmethyl)-n-methylamino)propyl)-5h-dibenz(
4’-chloro-2-((3-(10,11-dihydro-5h-dibenz(b,f)azepin-5-yl)propyl)methylamino)
n-methyl-n-(4’-chlorophenacyl)-3-(10,11-dihydro-5h-dibenzo(b,f)azepin-5-yl)p
acetophenone,4’-chloro-2-((3-(10,11-dihydro-5h-dibenz(b,f)azepin-5-yl)propyl)m
N-(4-CHLOROBENZOYLMETHYL)-3-(10,11-DIHYDRO-5H-DIBENZ[B,F]AZEPIN-5-YL)-N-METHYLPROPYLAMINE HYDROCHLORIDE
1-(4-chlorophenyl)-2-[[3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)propyl]methylamino]ethan-1-one monohydrochloride
[EINECS(EC#)]

248-002-2
[Molecular Formula]

C26H28Cl2N2O
[MDL Number]

MFCD00941486
[MOL File]

26786-32-3.mol
[Molecular Weight]

455.42
Chemical PropertiesBack Directory
[Melting point ]

152-154°
[Fp ]

9℃
[storage temp. ]

2-8°C
[solubility ]

DMSO: ~24 mg/mL
[form ]

solid
[color ]

off-white
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

22-37-53
[Safety Statements ]

22-24/25-26-28-36/37/39-38
[RIDADR ]

UN1230 - class 3 - PG 2 - Methanol, solution
[WGK Germany ]

2
[RTECS ]

AM6485000
[Toxicity]

LD50 in mice, rats (mg/kg): >2500, >1000 orally; 920, >1000 i.p.; >1000, >1000 s.c. (Eriksoo, Rohte)
Hazard InformationBack Directory
[Originator]

Gamonil,E. Merck
[Uses]

Lofepramine Hydrochloride is a tricyclic anti-depressent drug. Potent inhibitor of noradenaline uptake.
[Uses]

Monoamine reuptake inhibitor; tricyclic antidepressant.
[Definition]

ChEBI: Lofepramine hydrochloride is a hydrochloride. It has a role as an antidepressant. It contains a lofepramine.
[Manufacturing Process]

9.8 parts of 10,11-dihydro-5H-dibenzo[b,f]azepine are dissolved in 10 parts of dry toluene and 3.1 parts of sodium amide are added and the mixture is refluxed and stirred for four hours. A solution of 13.5 parts of 1-(4- chlorophenyl)-2-[(3-chloropropyl)methylamino]ethanone in 20 parts of dry toluene is added dropwise and the mixture is stirred and refluxed for eight hours.
After cooling to room temperature water is carefully added to the reaction mixture and the toluene solution is extracted with water to which hydrochloric acid is added so that the aqueous phase obtains the pH-value of 5. The aqueous extract is discarded and the toluene phase is evaporated to dryness in vacuum. The residue is dissolved in 50 parts of methanol. Hydrogen gas is introduced to give the crystalline hydrochloride 1-(4-chlorophenyl)-2-((3- (10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)methylamino)ethanone; MP: 154°-156°C. The hydrochloride may be removed by adding an equivalent of any base (triethyl amine, sodium hydroxide and so on).
[Therapeutic Function]

Antidepressant
[Biological Activity]

Lofepramine is an antidepressant; serotonin and norepinephrine re-uptake inhibitor (SNRI).
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