Trimipramine information

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.^[6]^[7]^[8]^[9] It has also been used for its sedative, anxiolytic, and weak antipsychotic effects in the treatment of insomnia, anxiety disorders, and psychosis, respectively.^[6]^[7]^[8]^[9] 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.^[10] Similarly to other TCAs, however, trimipramine does have antihistamine, antiserotonergic, antiadrenergic, antidopaminergic, and anticholinergic activities.^[6]^[7]^[8]^[9]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ ^a ^b ^c ^d ^e "PRODUCT INFORMATION SURMONTIL Tablets and Capsules" (PDF). TGA eBusiness Services. Aspen Pharmacare Australia Pty Ltd. 28 November 2012. Retrieved 30 November 2013.
^ ^a ^b ^c ^d ^e "SURMONTIL (trimipramine maleate) capsule [Duramed Pharmaceuticals Inc]". DailyMed. Duramed Pharmaceuticals Inc. December 2012. Retrieved 30 November 2013.
^ ^a ^b ^c ^d ^e "Surmontil, Trimip (trimipramine) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 30 November 2013.
^ ^a ^b ^c ^d ^e "Trimipramine 50mg Capsules - Summary of Product Characteristics (SPC)". electronic Medicines Compendium. Zentiva. 19 November 2012. Retrieved 30 November 2013.
^ ^a ^b ^c Berger M, Gastpar M (1996). "Trimipramine: a challenge to current concepts on antidepressives". Eur Arch Psychiatry Clin Neurosci. 246 (5): 235–9. doi:10.1007/bf02190274. PMID 8863001. S2CID 29596291.
^ ^a ^b ^c Gastpar M (1989). "Clinical originality and new biology of trimipramine". Drugs. 38 (Suppl 1): 43–8, discussion 49–50. doi:10.2165/00003495-198900381-00010. PMID 2693055. S2CID 23302529.
^ ^a ^b ^c Pecknold JC, Luthe L (1989). "Trimipramine, anxiety, depression and sleep". Drugs. 38 (Suppl 1): 25–31, discussion 49–50. doi:10.2165/00003495-198900381-00007. PMID 2693052. S2CID 20347877.
^ ^a ^b ^c Lapierre YD (1989). "A review of trimipramine. 30 years of clinical use". Drugs. 38 (Suppl 1): 17–24, discussion 49–50. doi:10.2165/00003495-198900381-00006. PMID 2693051. S2CID 22227558.
^ Cite error: The named reference pmid9090573 was invoked but never defined (see the help page).

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[TGA-2] "PRODUCT INFORMATION SURMONTIL Tablets and Capsules" (PDF). TGA eBusiness Services. Aspen Pharmacare Australia Pty Ltd. 28 November 2012. Retrieved 30 November 2013.

[DM-3] "SURMONTIL (trimipramine maleate) capsule [Duramed Pharmaceuticals Inc]". DailyMed. Duramed Pharmaceuticals Inc. December 2012. Retrieved 30 November 2013.

[MSR-4] "Surmontil, Trimip (trimipramine) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 30 November 2013.

[EMC-5] "Trimipramine 50mg Capsules - Summary of Product Characteristics (SPC)". electronic Medicines Compendium. Zentiva. 19 November 2012. Retrieved 30 November 2013.

[pmid8863001-6] Berger M, Gastpar M (1996). "Trimipramine: a challenge to current concepts on antidepressives". Eur Arch Psychiatry Clin Neurosci. 246 (5): 235–9. doi:10.1007/bf02190274. PMID 8863001. S2CID 29596291.

[pmid2693055-7] Gastpar M (1989). "Clinical originality and new biology of trimipramine". Drugs. 38 (Suppl 1): 43–8, discussion 49–50. doi:10.2165/00003495-198900381-00010. PMID 2693055. S2CID 23302529.

[pmid2693052-8] Pecknold JC, Luthe L (1989). "Trimipramine, anxiety, depression and sleep". Drugs. 38 (Suppl 1): 25–31, discussion 49–50. doi:10.2165/00003495-198900381-00007. PMID 2693052. S2CID 20347877.

[pmid2693051-9] Lapierre YD (1989). "A review of trimipramine. 30 years of clinical use". Drugs. 38 (Suppl 1): 17–24, discussion 49–50. doi:10.2165/00003495-198900381-00006. PMID 2693051. S2CID 22227558.

[pmid9090573-10] Cite error: The named reference pmid9090573 was invoked but never defined (see the help page).

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