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Details

Stereochemistry RACEMIC
Molecular Formula C20H26N2
Molecular Weight 294.4346
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIMIPRAMINE

SMILES

CC(CN(C)C)CN1c2ccccc2CCc3ccccc31

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 294.4346
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

2.97993601E11
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
Differential effects of trimipramine and fluoxetine on sleep in geriatric depression.
2001 Mar
Polysomnographic effects of adjuvant ginkgo biloba therapy in patients with major depression medicated with trimipramine.
2001 Mar
The use of antidepressant drugs in dermatology.
2001 Nov
Perazine for schizophrenia.
2002
Hydrophobia as a rare presentation of Cotard's syndrome: a case report.
2002 Aug
Effects of the atypical antidepressant trimipramine on neuronal excitability and long-term potentiation in guinea pig hippocampal slices.
2002 Feb
[Delusional depression as differential dementia of the Alzheimer type diagnosis].
2002 May
Is the nonREM-REM sleep cycle reset by forced awakenings from REM sleep?
2002 Nov
Enantiomers' potential in psychopharmacology--a critical analysis with special emphasis on the antidepressant escitalopram.
2002 Oct
Trimipramine in primary insomnia: results of a polysomnographic double-blind controlled study.
2002 Sep
Current use of selective serotonin reuptake inhibitors and risk of acute myocardial infarction.
2004
[Hypotensive cardio-circulatory failure and metabolic acidosis after suicidal intoxication with trimipramine and quetiapine. Case report and background].
2004 Jan
Severe adverse drug reactions of antidepressants: results of the German multicenter drug surveillance program AMSP.
2004 Mar
Contribution of sleep research to the development of new antidepressants.
2005
Sleep and psychiatry.
2005
Protonation of trimipramine salts of maleate, mesylate and hydrochloride observed by 1H, 13C and 15N NMR spectroscopy.
2005 Feb
Fluoxetine versus trimipramine in the treatment of depression in geriatric patients.
2005 Jan
2,2'-Bipyridine as a new and sensitive spectrophotometric reagent for the determination of nanoamounts of certain dibenzazepine class of tricyclic antidepressant drugs.
2005 Jan
[Multiple fibromas in systemic mastocytosis].
2005 May
Depression and sleep: pathophysiology and treatment.
2006
Perazine for schizophrenia.
2006 Apr 19
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Solid-phase extraction and analysis of 20 antidepressant drugs in human plasma by LC/MS with SSI method.
2006 Oct 16
Quantitative determination of forty-eight antidepressants and antipsychotics in human serum by HPLC tandem mass spectrometry: a multi-level, single-sample approach.
2006 Oct 20
An electrospray ionisation tandem mass spectrometric investigation of selected psychoactive pharmaceuticals and its application in drug and metabolite profiling by liquid chromatography/electrospray ionisation tandem mass spectrometry.
2007
Shifts in metabolic parameters surrounding glucose homoeostasis resulting from tricyclic antidepressant therapy: implications of insulin resistance?
2007 Jan
Quantification of tricyclic antidepressants and monoamine oxidase inhibitors by high-performance liquid chromatography-tandem mass spectrometry in whole blood.
2007 May
Pharmacokinetic genes do not influence response or tolerance to citalopram in the STAR*D sample.
2008 Apr 2
Pharmacogenetics: data, concepts and tools to improve drug discovery and drug treatment.
2008 Feb
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
Acid sphingomyelinase inhibitors normalize pulmonary ceramide and inflammation in cystic fibrosis.
2010 Jun
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 Fri Jun 25 22:33:19 UTC 2021
Edited
by admin
on Fri Jun 25 22:33:19 UTC 2021
Record UNII
6S082C9NDT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
7162 RP
Code English
TRIMEPROPRIMINE
Common Name English
5H-DIBENZ(B,F)AZEPINE-5-PROPANAMINE, 10,11-DIHYDRO-N,N,.BETA.-TRIMETHYL-
Systematic Name English
TRIMIPRAMINE [WHO-DD]
Common 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 Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
WHO-ATC N06AA06
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
WHO-VATC QN06AA06
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
NCI_THESAURUS C94727
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
LIVERTOX 1004
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
Code System Code Type Description
EVMPD
SUB11314MIG
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
RXCUI
10834
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C61990
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
DRUG CENTRAL
2758
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
LACTMED
Trimipramine
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
ECHA (EC/EINECS)
212-008-3
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
DRUG BANK
DB00726
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
EPA CompTox
739-71-9
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
INN
1414
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
IUPHAR
7317
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
FDA UNII
6S082C9NDT
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
MERCK INDEX
M11164
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY Merck Index
CAS
739-71-9
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
PUBCHEM
5584
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
MESH
D014299
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
WIKIPEDIA
TRIMIPRAMINE
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
PRIMARY
ChEMBL
CHEMBL644
Created by admin on Fri Jun 25 22:33:19 UTC 2021 , Edited by admin on Fri Jun 25 22:33:19 UTC 2021
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
Related Record Type Details
ACTIVE MOIETY