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Details

Stereochemistry RACEMIC
Molecular Formula C20H26N2
Molecular Weight 294.4338
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIMIPRAMINE

SMILES

CC(CN(C)C)CN1C2=CC=CC=C2CCC3=CC=CC=C13

InChI

InChIKey=ZSCDBOWYZJWBIY-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C20H26N2
Molecular Weight 294.4338
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Trimipramine is a tricyclic antidepressant similar to imipramine, but with more antihistaminic and sedative properties. It was sold under brand name surmontil for the relief of symptoms of depression. Endogenous depression is more likely to be alleviated than other depressive states. In studies with neurotic outpatients, the drug appeared to be equivalent to amitriptyline in the less-depressed patients but somewhat less effective than amitriptyline in the more severely depressed patients. In hospitalized depressed patients, trimipramine and imipramine were equally effective in relieving depression. Trimipramine has been reported to differ from other typical tricyclic antidepressant drugs in several aspects, for instance it does not inhibit neuronal transmitter uptake and does not cause down-regulation of beta-adrenoceptors. Moreover, it may possess antipsychotic activity in schizophrenic patients. In addition, was found that it did not antagonize the inhibitory effect of noradrenaline and 5-hydroxytryptamine on the release of transmitter, mediated by presynaptic auto receptors. In radioligand binding studies, trimipramine showed fairly high affinities for some dopamine (DA), noradrenaline and 5-hydroxytryptamine (5-HT) receptor subtypes (5-HT2 receptors = alpha 1A/B-adrenoceptors greater than or equal to D2 receptors), intermediate affinities for D1 receptors, alpha 2B-adrenoceptors and 5-HT1C receptors but only low affinities for alpha 2A-adrenoceptors, 5-HT1A, 5-HT1D and 5-HT3 receptors. It may thus be classified as an atypical neuroleptic drug.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SURMONTIL

Approved Use

SURMONTIL is indicated for the relief of symptoms of depression. Endogenous depression is more likely to be alleviated than other depressive states. In studies with neurotic outpatients, the drug appeared to be equivalent to amitriptyline in the less-depressed patients but somewhat less effective than amitriptyline in the more severely depressed patients. In hospitalized depressed patients, trimipramine and imipramine were equally effective in relieving depression.

Launch Date

1979
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
92.1 ng/mL
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2.13 μg × h/mL
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
31 h
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIMIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
[Instead of benzodiazepines. An antidepressant as sleep aid].
2001 Jan 18
[Delusional depression as differential dementia of the Alzheimer type diagnosis].
2002 May
Enantiomers' potential in psychopharmacology--a critical analysis with special emphasis on the antidepressant escitalopram.
2002 Oct
Antidepressants are functional antagonists at the serotonin type 3 (5-HT3) receptor.
2003 Nov
Severe adverse drug reactions of antidepressants: results of the German multicenter drug surveillance program AMSP.
2004 Mar
Antidepressants and their effect on sleep.
2005 Dec
Solid-phase extraction and analysis of 20 antidepressant drugs in human plasma by LC/MS with SSI method.
2006 Oct 16
Antidepressant therapy in tinnitus.
2007 Apr
Heart rate variability reveals risk of arrhythmias after intoxication with antidepressants.
2007 Jan
Antidepressant interactions with the NMDA NR1-1b subunit.
2008
Pharmacogenetics: data, concepts and tools to improve drug discovery and drug treatment.
2008 Feb
Diverse antidepressants increase CDP-diacylglycerol production and phosphatidylinositide resynthesis in depression-relevant regions of the rat brain.
2008 Jan 24
Determination of tricyclic antidepressants in human plasma using pipette tip solid-phase extraction and gas chromatography-mass spectrometry.
2008 Jul
Depression following thrombotic cardiovascular events in elderly medicare beneficiaries: risk of morbidity and mortality.
2009
Efficacy of tricyclic antidepressants in irritable bowel syndrome: a meta-analysis.
2009 Apr 7
Accuracy of Veterans Affairs databases for diagnoses of chronic diseases.
2009 Oct
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Role of human UGT2B10 in N-glucuronidation of tricyclic antidepressants, amitriptyline, imipramine, clomipramine, and trimipramine.
2010 May
Patents

Sample Use Guides

Outpatients and Office Patients: initially, 75 mg/day in divided doses, increased to 150 mg/day. Dosages over 200 mg/day are not recommended. Maintenance therapy is in the range of 50 to 150 mg/day. For convenient therapy and to facilitate patient compliance, the total dosage requirement may be given at bedtime. Hospitalized Patient: initially, 100 mg/day in divided doses. This may be increased gradually in a few days to 200 mg/day, depending upon individual response and tolerance. If improvement does not occur in 2 to 3 weeks, the dose may be increased to the maximum recommended dose of 250 to 300 mg/day. Adolescent and Geriatric Patients: initially, a dose of 50 mg/day is recommended, with gradual increments up to 100 mg/day, depending upon patient response and tolerance.
Route of Administration: Oral
It was investigated whether trimipramine and three of its metabolites interact with targets of other antidepressants, namely, the human monoamine transporters for noradrenaline (hNAT), serotonin (hSERT), and dopamine (hDAT), and with the human organic cation transporters (hOCT1, hOCT2, and hOCT3) which are expressed in the brain and are known to be involved in the uptake of monoamines. HEK293 cells heterologously expressing the abovementioned transporters were used to determine the inhibition of [(3)H]MPP(+) uptake by trimipramine and its main metabolites. At concentrations up to 30 μM, all transporters, except hOCT3, were inhibited by all examined substances. With IC(50) values between 2 and 10 μM, trimipramine inhibited hSERT, hNAT, hOCT1, and hOCT2, whereas clearly higher concentrations were needed for half-maximal inhibition of hDAT. Desmethyl-trimipramine showed about the same potencies as trimipramine, whereas 2-hydroxy-trimipramine was less potent at hNAT, hSERT, and hOCT1. Trimipramine-N-oxide preferentially inhibited hSERT.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:56:07 GMT 2025
Edited
by admin
on Mon Mar 31 18:56:07 GMT 2025
Record UNII
6S082C9NDT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
7162 RP
Preferred Name English
TRIMIPRAMINE
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
IL 6001
Code English
TRIMIPRAMINE [VANDF]
Common Name English
trimipramine [INN]
Common Name English
TRIMIPRAMINE [USAN]
Common Name English
5-(3-(DIMETHYLAMINO)-2-METHYLPROPYL)-10,11-DIHYDRO-5H-DIBENZ(B,F)AZEPINE
Systematic Name English
Trimipramine [WHO-DD]
Common Name English
TRIMEPROPRIMINE
Common Name English
5H-DIBENZ(B,F)AZEPINE-5-PROPANAMINE, 10,11-DIHYDRO-N,N,.BETA.-TRIMETHYL-
Systematic Name English
TRIMIPRAMINE [MART.]
Common Name English
7162-RP
Code English
TRIMIPRAMINE [MI]
Common Name English
IL-6001
Code English
Classification Tree Code System Code
NDF-RT N0000175752
Created by admin on Mon Mar 31 18:56:08 GMT 2025 , Edited by admin on Mon Mar 31 18:56:08 GMT 2025
WHO-ATC N06AA06
Created by admin on Mon Mar 31 18:56:08 GMT 2025 , Edited by admin on Mon Mar 31 18:56:08 GMT 2025
WHO-VATC QN06AA06
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
NCI_THESAURUS C94727
Created by admin on Mon Mar 31 18:56:08 GMT 2025 , Edited by admin on Mon Mar 31 18:56:08 GMT 2025
LIVERTOX NBK547855
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
Code System Code Type Description
EVMPD
SUB11314MIG
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
PRIMARY
RXCUI
10834
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C61990
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
PRIMARY
DRUG CENTRAL
2758
Created by admin on Mon Mar 31 18:56:08 GMT 2025 , Edited by admin on Mon Mar 31 18:56:08 GMT 2025
PRIMARY
LACTMED
Trimipramine
Created by admin on Mon Mar 31 18:56:08 GMT 2025 , Edited by admin on Mon Mar 31 18:56:08 GMT 2025
PRIMARY
DAILYMED
6S082C9NDT
Created by admin on Mon Mar 31 18:56:08 GMT 2025 , Edited by admin on Mon Mar 31 18:56:08 GMT 2025
PRIMARY
ECHA (EC/EINECS)
212-008-3
Created by admin on Mon Mar 31 18:56:08 GMT 2025 , Edited by admin on Mon Mar 31 18:56:08 GMT 2025
PRIMARY
DRUG BANK
DB00726
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
PRIMARY
EPA CompTox
DTXSID8023715
Created by admin on Mon Mar 31 18:56:08 GMT 2025 , Edited by admin on Mon Mar 31 18:56:08 GMT 2025
PRIMARY
INN
1414
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
PRIMARY
IUPHAR
7317
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
PRIMARY
FDA UNII
6S082C9NDT
Created by admin on Mon Mar 31 18:56:08 GMT 2025 , Edited by admin on Mon Mar 31 18:56:08 GMT 2025
PRIMARY
MERCK INDEX
m11164
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
PRIMARY Merck Index
CAS
739-71-9
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
PRIMARY
SMS_ID
100000076927
Created by admin on Mon Mar 31 18:56:08 GMT 2025 , Edited by admin on Mon Mar 31 18:56:08 GMT 2025
PRIMARY
PUBCHEM
5584
Created by admin on Mon Mar 31 18:56:08 GMT 2025 , Edited by admin on Mon Mar 31 18:56:08 GMT 2025
PRIMARY
MESH
D014299
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
PRIMARY
WIKIPEDIA
TRIMIPRAMINE
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
PRIMARY
CHEBI
9738
Created by admin on Mon Mar 31 18:56:08 GMT 2025 , Edited by admin on Mon Mar 31 18:56:08 GMT 2025
PRIMARY
ChEMBL
CHEMBL644
Created by admin on Mon Mar 31 18:56:07 GMT 2025 , Edited by admin on Mon Mar 31 18:56:07 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE -> PARENT
MAJOR
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ACTIVE MOIETY