Structure via PubChem · Public domain (PubChem)
imipramine
Sign in to saveAlso 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 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1959
- Admin. routes
- oral, parenteral
- Indications
- gastroesophageal reflux disease, anxiety, Dementia, myocardial infarction
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 280.194
- Has use
- medication
Show 8 more facts
- significant drug interaction
- tryptophan
- chemical formula
- C₁₉H₂₄N₂
- medical condition treated
- depression
- canonical SMILES
- CN(C)CCCN1C2=CC=CC=C2CCC3=CC=CC=C31
- World Health Organisation international non-proprietary name
- imipramine
- subject has role
- tricyclic antidepressant
- Commons category
- Imipramine
- physically interacts with
- solute carrier family 6 member 4
Sources (6)
via Wikidata · CC0
~16 min read
Encyclopedic overview
18 sectionsContents
- 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
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.
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.
Excerpted from Wikipedia’s “imipramine” article, available under the CC BY-SA 4.0 licence.