Trimipramine

Trimipramine
Clinical data
Trade names	Surmontil, others
Other names	Trimeproprimine; IF-6120; IL-6001; RP-7162; 2'-Methylimipramine; β-Methylimipramine
AHFS/Drugs.com
MedlinePlus	a602010
License data	US FDA: Trimipramine;
Pregnancy; category	AU: C;
Routes of; administration	Oral, intramuscular injection, intravenous
ATC code	N06AA06 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	41%
Protein binding	94.9%
Metabolism	Hepatic
Elimination 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 ; 521-78-8 (maleate);
PubChem CID	5584;
IUPHAR/BPS	7317;
DrugBank	DB00726 ;
ChemSpider	5382 ;
UNII	6S082C9NDT;
KEGG	D00394 ;
ChEBI	CHEBI:9738 ;
ChEMBL	ChEMBL644 ;
CompTox Dashboard (EPA)	DTXSID8023715 ;
ECHA InfoCard	100.010.917
Chemical and physical data
Formula	C20H26N2
Molar mass	294.442 g·mol−1
3D model (JSmol)	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 ; Key:ZSCDBOWYZJWBIY-UHFFFAOYSA-N ;
	(verify)

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.