Structure via PubChem · Public domain (PubChem)
trimipramine
Sign in to saveAlso known as trimeprimine, 5-[3-(dimethylamino)-2-methylpropyl]-10,11-dihydro-5H-dibenz[b,f]azepine, beta-methylimipramine, 5-(gamma-dimethylamino-beta-methylpropyl)-10,11-dihydro-5H-dibenzo[b,f]azepine, trimeproprimine, 10,11-dihydro-N,N,beta-trimethyl-5H-dibenz[b,f]azepine-5-propanamine
Trimipramine, sold under the brand name Surmontil among others, is a tricyclic antidepressant (TCA) which is used to treat depression. It has also been used for its sedative, anxiolytic, and weak antipsychotic effects in the treatment of insomnia, anxiety disorders, and psychosis, respectively. The drug is described as an atypical or "second-generation" TCA because, unlike other TCAs, it seems to be a fairly weak monoamine reuptake inhibitor. Similarly to other TCAs, however, trimipramine does have antihistamine, antiserotonergic, antiadrenergic, antidopaminergic, and anticholinergic activitie
Key facts
- Drug.verifiedrevid
- 470616008
- Drug.IUPAC_name
- (±)-3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N,2-trimethylpropan-1-amine
- Drug.image
- Trimipramine2DACS.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.image2
- Trimipramine-ball-and-stick-model.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200px
- Drug.tradename
- Surmontil, others
- Drug.MedlinePlus
- a602010
- Drug.licence_US
- Trimipramine
- Drug.pregnancy_AU
- C
- Drug.pregnancy_US
- C
- Drug.legal_AU
- S4
- Drug.legal_BR
- C1
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C20H26N2
- Molecular weight
- 294.4 g/mol
- IUPAC name
- 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N,2-trimethylpropan-1-amine
- SMILES
- CC(CN1C2=CC=CC=C2CCC3=CC=CC=C31)CN(C)C
- InChIKey
- ZSCDBOWYZJWBIY-UHFFFAOYSA-N
- XLogP
- 5.8
- 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
- 1979
- Admin. routes
- oral
- Indications
- anxiety, Dementia, depressive disorder, schizophrenia
via ChEMBL · EBI
Research
558 papers- Trimipramine.2006
- Trimipramine.2012
- Trimipramine, anxiety, depression and sleep.Drugs · 1989
- Trimipramine.British medical journal · 1967
- Trimipramine: a challenge to current concepts on antidepressives.European archives of psychiatry and clinical neuroscience · 1996
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 294.209599
- Has use
- medication
Show 7 more facts
- chemical formula
- C₂₀H₂₆N₂
- significant drug interaction
- loxapine
- Commons category
- Trimipramine
- World Health Organisation international non-proprietary name
- trimipramine
- canonical SMILES
- CC(CN1C2=CC=CC=C2CCC3=CC=CC=C31)CN(C)C
- subject has role
- tricyclic antidepressant
- physically interacts with
- solute carrier family 6 member 4
Sources (1)
via Wikidata · CC0
~22 min read
Encyclopedic overview
21 sectionsContents
- Medical uses
- Contraindications
- Side effects
- List of side effects
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Monoamine reuptake inhibition
- Antihistamine activity
- As a hypnotic
- Antidopaminergic activity
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Availability
- In film
- References
Trimipramine, sold under the brand name Surmontil among others, is a tricyclic antidepressant (TCA) which is used to treat depression. It has also been used for its sedative, anxiolytic, and weak antipsychotic effects in the treatment of insomnia, anxiety disorders, and psychosis, respectively. The drug is described as an atypical or "second-generation" TCA because, unlike other TCAs, it seems to be a fairly weak monoamine reuptake inhibitor. Similarly to other TCAs, however, trimipramine does have antihistamine, antiserotonergic, antiadrenergic, antidopaminergic, and anticholinergic activities.
==Medical uses== Trimipramine's primary use in medicine is in the treatment of major depressive disorder, especially where sedation is helpful due to its prominent sedative effects. The drug is also an effective anxiolytic, and can be used in the treatment of anxiety. In addition to depression and anxiety, trimipramine is effective in the treatment of insomnia, and unlike most other hypnotics, does not alter the normal sleep architecture. In particular, it does not suppress REM sleep, and dreams are said to "brighten" during treatment.
Excerpted from Wikipedia’s “trimipramine” article, available under the CC BY-SA 4.0 licence.