imipramine

Also known as N-(gamma-Dimethylaminopropyl)iminodibenzyl, N-(γ-dimethylaminopropyl)iminodibenzyl, 3-(5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine, melipramine, 10,11-dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine, 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine

Imipramine, sold under the brand name Tofranil, among others, is a tricyclic antidepressant (TCA) mainly used in the treatment of depression. It is also effective in treating anxiety and panic disorder. Imipramine is taken by mouth.

Chemical data

Formula: C19H24N2
Molecular weight: 280.4 g/mol
IUPAC name: 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine
SMILES: CN(C)CCCN1C2=CC=CC=C2CCC3=CC=CC=C31
InChIKey: BCGWQEUPMDMJNV-UHFFFAOYSA-N
XLogP: 4.8
Polar surface area: 6.5 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Wikidata facts

Mass: 280.194

Show 4 more facts

chemical formula: C₁₉H₂₄N₂
canonical SMILES: CN(C)CCCN1C2=CC=CC=C2CCC3=CC=CC=C31
World Health Organisation international non-proprietary name: imipramine
Commons category: Imipramine

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Medical uses
Contraindications
Side effects
Overdose
Interactions
Pharmacology
Pharmacodynamics
Pharmacokinetics
Chemistry
History
Society and culture
Generic names
Brand names
Availability
Prescription trends
See also
References
Further reading

Common side effects of imipramine include dry mouth, drowsiness, dizziness, low blood pressure, rapid heart rate, urinary retention, and electrocardiogram changes. Overdose of the medication can result in death. Imipramine appears to work by increasing levels of serotonin and norepinephrine and by blocking certain serotonin, adrenergic, histamine, and cholinergic receptors.