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Skeletal formula of desipramine
Ball-and-stick model of the desipramine molecule
Trade namesNorpramin, Pertofrane, others
Other namesDesmethylimipramine; Norimipramine; EX-4355; G-35020; JB-8181; NSC-114901[1][2][3]
  • 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine
Clinical data
Drug classTricyclic antidepressant[4]
Main usesDepression, panic disorder, postherpetic neuralgia[5]
Side effectsDry mouth, constipation, blurry vision, low blood pressure with standing, sleepiness, weakness[5]
  • US: N (Not classified yet)
Routes of
By mouth, intramuscular injection
External links
Legal status
Protein binding91%[6]
MetabolismLiver (CYP2D6)[7]
Elimination half-life12–30 hours[6]
ExcretionUrine (70%), feces[6]
Chemical and physical data
Molar mass266.388 g·mol−1
3D model (JSmol)
  • c1cc3c(cc1)CCc2c(cccc2)N3CCCNC
  • InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3 checkY

Desipramine, sold under the brand name Norpramin among others, is a tricyclic antidepressant (TCA) used to treat depression, panic disorder, and postherpetic neuralgia.[5] While benefits may be seen within 5 days, up to 3 weeks may be required for full effects.[5]

Common side effects include dry mouth, constipation, blurry vision, low blood pressure with standing, sleepiness, and weakness.[5] Other side effects may include suicide, mania, arrythmias, and seizures.[5] Safety in pregnancy is unclear.[5] How it works is unclear, but is believed to involve effects on serotonin and norepinephrine.[5]

Desipramine was approved for medical use in the United States in 1964.[5] It is available as a generic medication.[4] In the United States 30 tablets of 100 mg costs about 25 USD as of 2021.[8] It has been widely used.[4]

Medical uses

Desipramine is primarily used for the treatment of depression.[9]

Evidence of benefit in attention-deficit hyperactivity disorder (ADHD) is only in the short term, and with concerns of side effects its overall usefulness is not clear.[10] Desipramine at very low doses is also used to help reduce the pain associated with functional dyspepsia.[11] It has also been tried, albeit with little evidence, in the treatment of cocaine dependence.[12] Evidence for usefulness in neuropathic pain is also poor.[13]


It is generally started at a dose of 75 to 150 mg per day though may be increased up to 300 mg per day.[5] The typical long term doses is 100 to 200 mg per day.[4]

Side effects

Desipramine tends to be less sedating than other TCAs and tends to produce fewer anticholinergic effects such as dry mouth, constipation, urinary retention, blurred vision, and cognitive or memory impairments.[14]


Desipramine is particularly toxic in cases of overdose, compared to other antidepressants.[15] Any overdose or suspected overdose of desipramine is considered to be a medical emergency and can result in death without prompt medical intervention.



Site Ki (nM) Species Ref
SERT 17.6–163 Human [17][18]
NET 0.63–3.5 Human [17][18]
DAT 3,190 Human [17]
5-HT1A ≥6,400 Human [19][20]
5-HT2A 115–350 Human [19][20]
5-HT2C 244–748 Rat [21][22]
5-HT3 ≥2,500 Rodent [22][23]
5-HT7 >1,000 Rat [24]
α1 23–130 Human [19][25][18]
α2 ≥1,379 Human [19][25][18]
β ≥1,700 Rat [26][27]
Cav2.2 410 Human [28]
D1 5,460 Human [29]
D2 3,400 Human [19][25]
H1 60–110 Human [19][25][30]
H2 1,550 Human [30]
H3 >100,000 Human [30]
H4 9,550 Human [30]
mACh 66–198 Human [19][25]
  M1 110 Human [31]
  M2 540 Human [31]
  M3 210 Human [31]
  M4 160 Human [31]
  M5 143 Human [31]
σ1 1,990–4,000 Rodent [32][33]
σ2 ≥1,611 Rat [16][33]
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.[34][35] Based on one study, it has the highest affinity for the norepinephrine transporter (NET) of any other TCA,[17] and is said to be the most noradrenergic[36] and the most selective for the NET of the TCAs.[34] 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.[34]

Desipramine has the weakest antihistamine and anticholinergic effects of the TCAs.[37][36][38] It tends to be slightly activating/stimulating rather than sedating, unlike most others TCAs.[36] Whereas other TCAs are useful for treating insomnia, desipramine can cause insomnia as a side effect due to its activating properties.[36] The drug is also not associated with weight gain, in contrast to many other TCAs.[36] Secondary amine TCAs like desipramine and nortriptyline have a lower risk of orthostatic hypotension than other TCAs,[39][40] although desipramine can still cause moderate orthostatic hypotension.[41]


Desipramine is the major metabolite of imipramine and lofepramine.[42]


Desipramine is a tricyclic compound, specifically a dibenzazepine, and possesses three rings fused together with a side chain attached in its chemical structure.[43] Other dibenzazepine TCAs include imipramine (N-methyldesipramine), clomipramine, trimipramine, and lofepramine (N-(4-chlorobenzoylmethyl)desipramine).[43][44] Desipramine is a secondary amine TCA, with its N-methylated parent imipramine being a tertiary amine.[45][46] Other secondary amine TCAs include nortriptyline and protriptyline.[47][48] The chemical name of desipramine is 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-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.[1] 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.[1][2] 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.[1][2][49]


Desipramine was developed by Geigy.[50] It first appeared in the literature in 1959 and was patented in 1962.[50] The drug was first introduced for the treatment of depression in 1963 or 1964.[50][51]

Society and culture

Generic names

Desipramine is the generic name of the drug and its INN and BAN, while desipramine hydrochloride is its USAN, USP, BAN, and JAN.[1][2][52][3] Its generic name in French and its DCF are désipramine, in Spanish and Italian and its DCIT are desipramina, in German is desipramin, and in Latin is desipraminum.[2][3]

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.[2][3]


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External links