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Imipramine, sold under the brand name Tofranil among others, is a tricyclic antidepressant (TCA) which is used mainly in the treatment of depression. It can also reduce symptoms of agitation and anxiety. The drug is also used to treat bedwetting. It is taken by mouth. A long-acting form for injection into muscle is also available.
Common side effects of imipramine include dry mouth, drowsiness, dizziness, low blood pressure, rapid heart rate, urinary retention, and electrocardiogram changes. Overdose can result in death. The drug appears to work by increasing levels of serotonin and norepinephrine and by blocking certain serotonin, adrenergic, histamine, and cholinergic receptors.
Imipramine was discovered in 1951 and was introduced for medical use in 1957. It was the first TCA to be marketed. Imipramine and the other TCAs have decreased in use in recent decades due to the introduction of the selective serotonin reuptake inhibitors (SSRIs), which have fewer side effects and are safer in overdose.
Contents
1 Medical uses
1.1 Available forms
2 Contraindications
3 Side effects
4 Overdose
5 Interactions
6 Pharmacology
6.1 Pharmacodynamics
6.2 Pharmacokinetics
7 Chemistry
8 History
9 Society and culture
9.1 Generic names
9.2 Brand names
9.3 Availability
10 References
11 External links
Medical uses
Imipramine is used in the treatment of depression, such as depression associated with agitation or anxiety. It is similar in efficacy to the antidepressant drug moclobemide. It has also been used to treat nocturnal enuresis because of its ability to shorten the time of delta wave stage sleep, where wetting occurs. In veterinary medicine, imipramine is used with xylazine to induce pharmacologic ejaculation in stallions.
Available forms
Imipramine is available in the form of oral tablets and as a formulation for depot intramuscular injection.
Contraindications
Combining it with alcohol consumption causes excessive drowsiness. It may be unsafe during pregnancy.
Side effects
Those listed in italics below denote common side effects.
Central nervous system: dizziness, drowsiness, confusion, seizures, headache, anxiety, tremors, stimulation, weakness, insomnia, nightmares, extrapyramidal symptoms in geriatric patients, increased psychiatric symptoms, paresthesia
Cardiovascular: orthostatic hypotension, ECG changes, tachycardia, hypertension, palpitations, dysrhythmias
Eyes, ears, nose and throat: blurred vision, tinnitus, mydriasis
Gastrointestinal: dry mouth, nausea, vomiting, paralytic ileus, increased appetite, cramps, epigastric distress, jaundice, hepatitis, stomatitis, constipation, taste change
Genitourinary: urinary retention
Hematological: agranulocytosis, thrombocytopenia, eosinophilia, leukopenia
Skin: rash, urticaria, diaphoresis, pruritus, photosensitivity
Overdose
Main articles: Tricyclic antidepressant § Overdose, and Tricyclic antidepressant overdose
Interactions
Main article: Tricyclic antidepressant § Interactions
Pharmacology
Pharmacodynamics
See also: Pharmacology of antidepressants and Tricyclic antidepressant § Binding profiles
Imipramine (and metabolite)
Site
IMI
DSI
Species
Ref
SERT
1.3–1.4
17.6–163
Human
NET
20–37
0.63–3.5
Human
DAT
8,500
3,190
Human
5-HT 1A
≥5,800
≥6,400
Human
5-HT 2A
80–150
115–350
Human
5-HT 2C
120
244–748
Human/rat
5-HT 3
970–3,651
≥2,500
Rodent
5-HT 6
190–209
ND
Rat
5-HT 7
>1,000
>1,000
Rat
α 1
32
23–130
Human
α 2
3,100
≥1,379
Human
β
>10,000
≥1,700
Rat
D 1
>10,000
5,460
Human
D 2
620–726
3,400
Human
D 3
387
ND
Human
H 1
7.6–37
60–110
Human
H 2
550
1,550
Human
H 3
>100,000
>100,000
Human
H 4
24,000
9,550
Human
mACh
46
66–198
Human
   M 1
42
110
Human
   M 2
88
540
Human
   M 3
60
210
Human
   M 4
112
160
Human
   M 5
83
143
Human
α3β4
410–970
ND
Human
σ 1
332–520
1,990–4,000
Rodent
σ 2
327–2,100
≥1,611
Rat
hERG
3,400
ND
Human
Values are K i (nM). The smaller the value, the more strongly the drug binds to the site.
Imipramine affects numerous neurotransmitter systems known to be involved in the etiology of depression, anxiety, attention-deficit hyperactivity disorder (ADHD), enuresis and numerous other mental and physical conditions. Imipramine is similar in structure to some muscle relaxants, and has a significant analgesic effect and, thus, is very useful in some pain conditions.
The mechanisms of imipramine’s actions include, but are not limited to, effects on:
Serotonin : very strong reuptake inhibition.
Norepinephrine : strong reuptake inhibition. Desipramine has more affinity to norepinephrine transporter than imipramine.
Dopamine : imipramine blocks D 2 receptors.
Acetylcholine : imipramine is an anticholinergic, specifically an antagonist of the muscarinic acetylcholine receptors. Thus, it is prescribed with caution to the elderly and with extreme caution to those with psychosis, as the general brain activity enhancement in combination with the “dementing” effects of anticholinergics increases the potential of imipramine to cause hallucinations, confusion and delirium in this population.
Epinephrine : imipramine antagonizes adrenergic receptors, thus sometimes causing orthostatic hypotension.
Sigma receptor : activity on sigma receptors is present, but it is very weak (K i = 520 nM) and it is about half that of amitriptyline (K i = 300 nM).
Histamine : imipramine is an antagonist of the histamine H 1 receptors.
BDNF : BDNF is implicated in neurogenesis in the hippocampus, and studies suggest that depressed patients have decreased levels of BDNF and reduced hippocampal neurogenesis. It is not clear how neurogenesis restores mood, as ablation of hippocampal neurogenesis in murine models do not show anxiety related or depression related behaviours. Chronic imipramine administration results in increased histone acetylation (which is associated with transcriptional activation and decondensed chromatin) at the hippocampal BDNF promotor, and also reduced expression of hippocampal HDAC5.
Pharmacokinetics
Within the body, imipramine is converted into desipramine (desmethylimipramine) as a metabolite.
Chemistry
Imipramine is a tricyclic compound, specifically a dibenzazepine, and possesses three rings fused together with a side chain attached in its chemical structure.
History
The parent compound of imipramine, 10,11-dihydro-5 H -dibenz[b,f]azepine (dibenzazepine), was first synthesized in 1899, but no pharmacological assessment of this compound or any substituted derivatives was undertaken until the late 1940s.
In the late 1950s, imipramine was the first TCA to be developed (by Ciba ). At the first international congress of neuropharmacology in Rome, September 1958 Dr Freyhan from the University of Pennsylvania discussed as one of the first clinicians the effects of imipramine in a group of 46 patients, most of them diagnosed as “depressive psychosis”. The patients were selected for this study based on symptoms such as depressive apathy, kinetic retardation and feelings of hopelessness and despair. In 30% of all patients, he reported optimal results, and in around 20%, failure. The side effects noted were atropine -like, and most patients suffered from dizziness. Imipramine was first tried against psychotic disorders such as schizophrenia, but proved ineffective. As an antidepressant, it did well in clinical studies and it is known to work well in even the most severe cases of depression. Such powerful antidepressant properties have made it favorable in the treatment of treatment-resistant depression.
Before the advent of selective serotonin reuptake inhibitors (SSRIs), its sometimes intolerable side-effect profile was considered more tolerable. Therefore, it became extensively used as a standard antidepressant and later served as a prototypical drug for the development of the later-released TCAs. Today it is no longer used as commonly, but is sometimes still prescribed as a second-line treatment for treating major depression. It has also seen limited use in the treatment of migraines, ADHD, and post-concussive syndrome. Imipramine has additional indications for the treatment of panic attacks, chronic pain, and Kleine-Levin syndrome. In pediatric patients, it is relatively frequently used to treat pavor nocturnus and nocturnal enuresis.
Society and culture
Generic names
Imipramine is the English and French generic name of the drug and its INN, BAN, and DCF, while imipramine hydrochloride is its USAN, USP, BANM, and JAN.
Brand names
Imipramine is marketed throughout the world mainly under the brand name Tofranil.
Availability
Imipramine is available for medical use widely throughout the world, including in the United States, the United Kingdom, elsewhere in Europe, South Africa, Australia, and New Zealand.

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