Desipramine hydrochloride

Chemical Properties

White To Off-White Solid

Originator

Pertofran,Geigy,UK,1963

Uses

Tricyclic antidepresant that is a more potent inhibitor of the norepinephrine transporter than the serotonin transporter.

Uses

Tricyclic antidepressant that is a more potent inhibitor of the norepinephrine transporter than the serotonin transporter.

Uses

Desipramine hydrochloride has been used:

• to prevent norepinephrine neuron degeneration and to maximize uptake into DA neurons
• to protect unselective damage to thenoradrenergic system
• as a norepinephrine re-uptake inhibitor to treat rats for lesioning

Definition

ChEBI: The hydrochloride salt of desipramine.

Manufacturing Process

Oxidative coupling of o-nitrotoluene gives 4,4'-dinitrodibenzyl which is reduced with hydrogen to the diamine. The diamine is pyrolyzed to give dihydrobenzazepine. This is reacted with N-(3-chloropropyl)-Nmethylbenzamine to give N-benzyldesipramine. This is debenzylated by reductive cleavage and then reacted with HCl.

brand name

Norpramin (Sanofi Aventis); Pertofrane (Sanofi Aventis).

Therapeutic Function

Psychostimulant

General Description

The structure and salient properties of desipramine hydrochloride,10,11-dihydro-N-methyl-5H-dibenz[b,f]azepine-5-propanamine monohydrochloride, 5-(3-methylaminopropyl)-10,11-dihydro-5H-dibenz[b,f]azepine hydrochloride(Norpramin, Pertofrane), are discussed under the heading,Imipramine. Among tricyclics, desipramine would be consideredwhen few anticholinergic effects or a low level of sedationare important. It is a SNERI.

Biological Activity

Tricyclic antidepressant that is a selective inhibitor of noradrenalin transporters (K i values are 4, 61 and 78720 nM for NET, SERT and DAT transporters respectively).

Biochem/physiol Actions

Desipramine is used to treat depression. It is also used to manage enuresis in children. Desipramine helps to eliminate the pain triggered by diabetic neuropathy.

Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Human systemic effects by ingestion: decreased urine volume, sodium level changes, chlorine level changes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of NO, and HCI.

storage

Desiccate at +4°C