I7379

Sigma-Aldrich

Imipramine hydrochloride

≥99% (TLC)

Synonym(s):
10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine hydrochloride, 5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine hydrochloride
Empirical Formula (Hill Notation):
C19H24N2 · HCl
CAS Number:
Molecular Weight:
316.87
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

assay

≥99% (TLC)

form

powder

color

white

solubility

H2O: 50 mg/mL

originator

Novartis

SMILES string

Cl[H].CN(C)CCCN1c2ccccc2CCc3ccccc13

InChI

1S/C19H24N2.ClH/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21;/h3-6,8-11H,7,12-15H2,1-2H3;1H

InChI key

XZZXIYZZBJDEEP-UHFFFAOYSA-N

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General description

Imipramine is a tricyclic antidepressant. It has a half-life of 6 to 20 hours. Imipramine is made up of a tricyclic nucleus, that consists of two phenyl rings and a central cycloheptadien ring.

Application

Imipramine hydrochloride has been used:
  • as a non- selective serotonin reuptake inhibitor (SSRI) tricyclic anti-depressant (DD-IMI) to treat animals
  • to investigate its interaction with insulin in aqueous solution
  • to abolish the ability of internalized lipoproteins to stimulate cholesteryl esterification

Packaging

5, 25, 100 g in glass bottle

Biochem/physiol Actions

Tricyclic antidepressant; inhibits the serotonin and norepinephrine transporters with Kis of 7.7 nM and 67 nM, respectively. Has little effect on the dopamine transporter (Ki = 25 μM).

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.
This compound is featured on the Biogenic Amine Transporters and Chloride Channels pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

pictograms

Skull and crossbones

signalword

Danger

hcodes

hazcat

Acute Tox. 2 Oral

storage_class_code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK Germany

WGK 1

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

Thermodynamic study of the imipramine-insulin interaction
Lopez-Fontan J, et al.
The Journal of Chemical Thermodynamics, 31(10), 1297-1306 (1999)
Direct retino-raphe projection alters serotonergic tone and affective behavior
Ren C, et al.
Neuropsychopharmacology, 38(7), 1163-1163 (2013)
Psychotropic drugs
Drugs During Pregnancy and Lactation, 743-774 (2015)
Yeqing Huang et al.
Biochemical and biophysical research communications, 518(2), 337-343 (2019-08-20)
The slow onset of traditional antidepressants has become an urgent clinical issue, researchers are constantly exploring new antidepressants with prompt action. Previous studies have found that zinc levels were decreased in serum and brain of depressed patients or animal models....
Low density lipoprotein receptor-related protein and gp330 bind similar ligands, including plasminogen activator-inhibitor complexes and lactoferrin, an inhibitor of chylomicron remnant clearance.
Willnow TE, et al.
Test, 267(36), 26172-26180 (1992)

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