Desipramine

 ( Alpha-1 Blockers ) 

Desipramine, sold under the brand name Norpramin among others, is a tricyclic antidepressant (TCA) used in the treatment of depression.

It acts as a relatively selective norepinephrine reuptake inhibitor, though it does also have other activities such as weak serotonin reuptake inhibitory, α₁-blocking, antihistamine, and anticholinergic effects. The drug has not been considered a first-line treatment for depression since the introduction of selective serotonin reuptake inhibitor (SSRI) , which have fewer and are safer in overdose.

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Medical uses Desipramine is primarily used for the treatment of depression. It may also be useful to treat symptoms of attention-deficit hyperactivity disorder (ADHD). Evidence of benefit is only in the short term, and with concerns of side effects its overall usefulness is not clear. Desipramine at very low doses is also used to help reduce the pain associated with functional dyspepsia. It has also been tried, albeit with little evidence of effectiveness, in the treatment of cocaine dependence. Evidence for usefulness in neuropathic pain is also poor.

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Side effects

Desipramine tends to be less sedation than other TCAs and tends to produce fewer anticholinergic effects such as dry mouth, constipation, urinary retention, blurred vision, and cognitive or memory impairments.

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Overdose

Desipramine is particularly toxic in cases of overdose, compared to other antidepressants. Any overdose or suspected overdose of desipramine is considered to be a medical emergency and can result in death without prompt medical intervention.

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Pharmacology

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Pharmacodynamics

+ Desipramine
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

Desipramine is a very potent and relatively selective norepinephrine reuptake inhibitor (NRI), which is thought to enhance noradrenergic neurotransmission. Based on one study, it has the highest affinity for the norepinephrine transporter (NET) of any other TCA, and is said to be the most noradrenergic and the most selective for the NET of the TCAs.

(2025). 9780781762144, Lippincott Williams & Wilkins. . ISBN 9780781762144

The observed effectiveness of desipramine in the treatment of ADHD was the basis for the development of the selective NRI atomoxetine and its use in ADHD.

Desipramine has the weakest antihistamine and anticholinergic effects of the TCAs.

(1984). 9780849356803, CRC Press. . ISBN 9780849356803

(2016). 9780323416917, Elsevier Health Sciences. . ISBN 9780323416917

(2025). 9781550092486, PMPH-USA. . ISBN 9781550092486

It tends to be slightly psychostimulant rather than sedative, unlike most others TCAs. Whereas other TCAs are useful for treating insomnia, desipramine can cause insomnia as a side effect due to its activating properties. The drug is also not associated with weight gain, in contrast to many other TCAs. Secondary amine TCAs like desipramine and nortriptyline have a lower risk of orthostatic hypotension than other TCAs,

(2012). 9781461559573, Springer Science & Business Media. . ISBN 9781461559573

(2025). 9781585629336, American Psychiatric Pub. . ISBN 9781585629336

although desipramine can still cause moderate orthostatic hypotension.

(2007). 9781437721904, Elsevier Health Sciences. . ISBN 9781437721904

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Pharmacokinetics

Desipramine is the major metabolite of imipramine and lofepramine.

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Chemistry

Desipramine is a tricyclic compound, specifically a dibenzazepine, and possesses three rings fused together with a side chain attached in its chemical structure.

(2013). 9789400758056, Springer Science & Business Media. . ISBN 9789400758056

Other dibenzazepine TCAs include imipramine ( N-methyldesipramine), clomipramine, trimipramine, and lofepramine ( N-(4-chlorobenzoylmethyl)desipramine).

(2025). 9780781768795, Lippincott Williams & Wilkins. . ISBN 9780781768795

Desipramine is a secondary amine TCA, with its N-methylation parent compound imipramine being a tertiary amine.

(1994). 9780471950523, John Wiley & Sons. . ISBN 9780471950523

(2012). 9783527646326, John Wiley & Sons. . ISBN 9783527646326

Other secondary amine TCAs include nortriptyline and protriptyline.

(2025). 9781560534709, Elsevier Health Sciences. . ISBN 9781560534709

(2012). 9780191626753, OUP Oxford. . ISBN 9780191626753

The chemical name of desipramine is 3-(10,11-dihydro-5 H-dibenzo b, fazepin-5-yl)- N-methylpropan-1-amine and its free base form has a chemical formula of C₁₈H₂₂N₂ with a molecular weight of 266.381 g/mol. The drug is used commercially mostly as the hydrochloride salt; the dibudinate salt is or has been used for intramuscular injection in Argentina (brand name Nebril) and the free base form is not used. The CAS Registry Number of the free base is 50-47-5, of the hydrochloride is 58-28-6, and of the dibudinate is 62265-06-9.

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History

Desipramine was developed by Geigy. It first appeared in the literature in 1959 and was patented in 1962. The drug was first introduced for the treatment of depression in 1963 or 1964.

(2025). 9780781728454, Lippincott Williams & Wilkins. . ISBN 9780781728454

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Society and culture

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Generic names

Desipramine is the generic term of the drug and its and , while desipramine hydrochloride is its , , , and .

(2014). 9781475720853, Springer. . ISBN 9781475720853

(2025). 9783887630751, Taylor & Francis. . ISBN 9783887630751

(2012). 9789401144391, Springer Science & Business Media. . ISBN 9789401144391

Its generic name in French language and its are désipramine, in Spanish language and Italian language and its are desipramina, in German language is desipramin, and in Latin language is desipraminum.

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Brand names

Desipramine is or has been marketed throughout the world under a variety of brand names, including Irene, Nebril, Norpramin, Pertofran, Pertofrane, Pertrofran, and Petylyl among others.

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External links

• Desipramine - MedlinePlus

Categories: Alpha-1 Blockers, Antihistamines, Cyp2a6 Inhibitors, Cyp2d6 Inhibitors, Dibenzazepines, Human Drug Metabolites, M1 Receptor Antagonists, M2 Receptor Antagonists, M3 Receptor Antagonists, M4 Receptor Antagonists, M5 Receptor Antagonists, Norepinephrine Reuptake Inhibitors, Secondary Amines, Serotonin Receptor Antagonists, Sodium Channel Blockers, Stimulants, Tricyclic Antidepressants, Wakefulness-promoting Agents

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