DIBENZEPIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H21N3O
Molecular Weight	295.3788
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCN1C2=CC=CC=C2N(C)C3=CC=CC=C3C1=O

InChI

InChIKey=QPGGEKPRGVJKQB-UHFFFAOYSA-N

InChI=1S/C18H21N3O/c1-19(2)12-13-21-17-11-7-6-10-16(17)20(3)15-9-5-4-8-14(15)18(21)22/h4-11H,12-13H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C18H21N3O
Molecular Weight	295.3788
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: Leigh, D., Pare, C.M., Marks, J. (2012) A Concise Encyclopaedia of Psychiatry, page 380, retrieved from: https://books.google.ru/books?id=o-bzCAAAQBAJ
Curator's Comment: Description was created based on several sources, including http://mentalhealthdaily.com/2014/08/18/tricyclic-antidepressants-list-tcas/

Dibenzepin is a tricyclic antidepressant of the dibenzo-epine group. It is a selective noradrenaline uptake inhibitor, which exhibits in vitro and in vivo imipramine-like effects. It binds strongly to histamine H1 receptors in the brain and, to a lesser extent, to cholinergic receptors. The pharmacological profile of dibenzepin corresponds widely to its biochemical properties: histamine antagonism, tetrabenazine antagonism, potentiation of various noradrenergic effects and anticholinergic effects. Dibenzepin is only available in European countries for the treatment of depression.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: http://www.pharmawiki.ch/wiki/index.php?wiki=Dibenzepin	Antagonist 2849
Monoamine transporter 10 Target ID: CHEMBL2363064 Sources: http://www.kegg.jp/entry/D07812	Inhibitor 8504
Muscarinic acetylcholine receptor 162 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20647 \| https://www.old.health.gov.il/units/pharmacy/trufot/alonim/4401.pdf	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5492203	Primary		Approved 8583	NOVERIL Approved Use Noveril (dibenzepin) is indicated for the treatment of depression

Doses

Dose	Population	Adverse events
14.4 g single, oral Overdose Dose: 14.4 g Route: oral Route: single Dose: 14.4 g Sources: https://pubmed.ncbi.nlm.nih.gov/6138296/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6138296/	Other AEs: Seizures... Other AEs: Seizures Sources: https://pubmed.ncbi.nlm.nih.gov/6138296/
2160 mg single, oral Overdose Dose: 2160 mg Route: oral Route: single Dose: 2160 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8826563/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8826563/	Other AEs: Pulmonary edema... Other AEs: Pulmonary edema Sources: https://pubmed.ncbi.nlm.nih.gov/8826563/

AEs

AE	Significance	Dose	Population
Seizures		14.4 g single, oral Overdose Dose: 14.4 g Route: oral Route: single Dose: 14.4 g Sources: https://pubmed.ncbi.nlm.nih.gov/6138296/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6138296/
Pulmonary edema		2160 mg single, oral Overdose Dose: 2160 mg Route: oral Route: single Dose: 2160 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8826563/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8826563/

PubMed

Title	Date	PubMed
Tricyclic antidepressants and headaches: systematic review and meta-analysis.	2010-10-20	20961988
Inhibition of the cardiac L-type calcium channel current by antidepressant drugs.	2008-03	18048694
Comparison of trazodone, diazepame and dibenzepine influences on rat brain beta-endorphins content.	2007-08	17848146
Therapeutic drug monitoring of 13 antidepressant and five neuroleptic drugs in serum with liquid chromatography-electrospray ionization mass spectrometry.	2003-12	14708881
Precise gas chromatography with retention time locking in comprehensive toxicological screening for drugs in blood.	2003-05-25	12705964
Simultaneous determination of seven tricyclic antidepressant drugs in human plasma by direct-injection HPLC-APCI-MS-MS with an ion trap detector.	2002-08	12142640
Discrimination in 5-HT(3) receptor binding in murine brain and cultured cell preparations.	2002-02	11819030
Direct-injection high performance liquid chromatography ion trap mass spectrometry for the quantitative determination of olanzapine, clozapine and N-desmethylclozapine in human plasma.	2002	12112253
Drug-induced rapid cycling: possible outcomes and management.	1982-07	6124134
Dibenzepin and amitriptyline in the treatment of depression.	1971-05	5580367

Patents

Sample Use Guides

In Vivo Use Guide

In adult patients, treatment should begin with Noveril (dibenzepin) 240 mg tablets, the daily dose being given as a single dose or in 2 divided dose.

Route of Administration: Oral

In Vitro Use Guide

Dibenzepin blocked calcium current in enzymatically isolated rat ventricular myocytes with IC(50) values of 364 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:49:11 GMT 2025` Edited by `admin` on `Mon Mar 31 18:49:11 GMT 2025`
Record UNII	510SJZ1Y6L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

10-(2-(DIMETHYLAMINO)ETHYL)-5,10-DIHYDRO-5-METHYL-11-H-DIBENZO(B,E)(1,4)DIAZEPIN-11-ONE

Preferred Name

English

DIBENZEPIN

Official Name

English

DIBENZEPINE

Common Name

English

Dibenzepin [WHO-DD]

Common Name

English

DIBENZEPIN [MI]

Common Name

English

dibenzepin [INN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN06AA08