Trimipramine

Trimipramine

Clinical data
Trade names	Surmontil
AHFS/Drugs.com	Monograph
MedlinePlus	a602010
License data	US FDA: Trimipramine
Pregnancy category	AU: C US: C (Risk not ruled out)
Routes of administration	Oral, IM, IV
ATC code	N06AA10 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	41%
Protein binding	94.9%
Metabolism	Hepatic
Biological half-life	23-24 hours
Excretion	Renal
Identifiers
IUPAC name (±)-3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N,2-trimethylpropan-1-amine
CAS Number	739-71-9 Y
PubChem CID	5584
IUPHAR/BPS	7317
DrugBank	DB00726 Y
ChemSpider	5382 Y
UNII	6S082C9NDT
KEGG	D00394 Y
ChEBI	CHEBI:9738 Y
ChEMBL	CHEMBL644 Y
ECHA InfoCard	100.010.917
Chemical and physical data
Formula	C20H26N2
Molar mass	294.434 g/mol
3D model (Jmol)	Interactive image
SMILES c1cc3c(cc1)CCc2c(cccc2)N3CC(C)CN(C)C
InChI InChI=1S/C20H26N2/c1-16(14-21(2)3)15-22-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)22/h4-11,16H,12-15H2,1-3H3 Y Key:ZSCDBOWYZJWBIY-UHFFFAOYSA-N Y

Trimipramine (Surmontil, Rhotrimine, Stangyl) is a tricyclic antidepressant (TCA) with antipsychotic and sedative properties.

Trimipramine's primary use in medicine is in the treatment of major depressive disorder, especially where sedation is required due to its prominent sedative effects. Trimipramine also has some weak antipsychotic effects which are less pronounced than with the phenothiazine antipsychotic perazine.

Trimipramine is the only effective drug against insomnia known so far that does not alter the normal sleep architecture (there is evidence in medical journals that refute this last statement). In particular, it does not suppress REM sleep, and dreams are said to brighten during treatment.

Common adverse effects include:

Note: Bolded adverse effects are serious ones.

whereas adverse effects with an unknown incidence includes:

and rare adverse effects include:

Contraindications include:

Trimipramine should not be given with sympathomimetic agents such as adrenaline, ephedrine, isoprenaline, noradrenaline, phenylephrine and phenylpropanolamine.

Barbiturates may increase the rate of metabolism. Trimipramine should be administered with care in patients receiving therapy for hyperthyrodism.

Compared to other tricyclic antidepressants trimipramine is relatively safe in overdose, although it is more dangerous than the selective serotonin reuptake inhibitors (SSRIs) and serotonin-norepinephrine reuptake inhibitors (SNRIs) but less dangerous than bupropion in cases of overdose.