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I7379

Sigma-Aldrich

Imipramine hydrochloride

≥99% (TLC)

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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:
113-52-0
Molecular Weight:
316.87
EC Number:
204-030-7
MDL number:
MFCD00012669
PubChem Substance ID:
24278097

Quality Level

200

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

Gene Information

human ... HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR1E(3354) , HTR1F(3355) , HTR2A(3356) , HTR2B(3357) , HTR2C(3358) , HTR3A(3359) , HTR3B(9177) , HTR3C(170572) , HTR3D(200909) , HTR3E(285242) , HTR4(3360) , HTR5A(3361) , HTR5B(645694) , HTR6(3362) , HTR7(3363) , SLC6A2(6530) , SLC6A4(6532)

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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

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 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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

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

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Psychotropic drugs
Drugs During Pregnancy and Lactation, 743-774 (2015)
Thermodynamic study of the imipramine-insulin interaction
Lopez-Fontan J, et al.
The Journal of Chemical Thermodynamics, 31(10), 1297-1306 (1999)
Attention Deficit Hyperactivity Disorder
Comprehensive Medicinal Chemistry II.: Global perspective (2007)
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)
Direct retino-raphe projection alters serotonergic tone and affective behavior
Ren C, et al.
Neuropsychopharmacology, 38(7), 1163-1163 (2013)
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