U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H23N3
Molecular Weight 305.4167
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIANOPRAMINE

SMILES

CN(C)CCCN1C2=CC=CC=C2CCC3=CC=C(C=C13)C#N

InChI

InChIKey=LQXYCDLHSKICDY-UHFFFAOYSA-N
InChI=1S/C20H23N3/c1-22(2)12-5-13-23-19-7-4-3-6-17(19)10-11-18-9-8-16(15-21)14-20(18)23/h3-4,6-9,14H,5,10-13H2,1-2H3

HIDE SMILES / InChI
Cianopramine is a highly potent inhibitor of neuronal serotonin (5-HT) uptake developed by Hoffmann-La Roche for major depression treatment. In preclinical studies, acute and chronic treatment with Cianopramine shows clear behavioural effects Cianopramine increases neophobic reactions in the free exploration test, the avoidance reaction to a brightly illuminated chamber in the light/dark choice procedure as well as to open arms in the elevated plus-maze test. In a double-blind trial, Cianopramine effective in reducing scores on the Hamilton Psychiatric Rating Scale for Depression and on a global scale. Unfortunately, Cianopramine administrations were associated with significant adverse effects and future development was discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Selective alterations of the CB1 receptors and the fatty acid amide hydrolase in the ventral striatum of alcoholics and suicides.
2010-07
Determination of moxifloxacin in human plasma, plasma ultrafiltrate, and cerebrospinal fluid by a rapid and simple liquid chromatography- tandem mass spectrometry method.
2010-04
Differential regulation of serotonin-1A receptor-stimulated [35S]GTP gamma S binding in the dorsal raphe nucleus by citalopram and escitalopram.
2008-03-31
Architectonic distribution of the serotonin transporter within the orbitofrontal cortex of the vervet monkey.
2007-09-21
Serotonin transporter function, but not expression, is dependent on brain-derived neurotrophic factor (BDNF): in vivo studies in BDNF-deficient mice.
2007-05
Comparative evaluation of two serotonin transporter ligands in the human brain: [(11)C](+)McN5652 and [(11)C]cyanoimipramine.
2002-10
A positive association between 5HT re-uptake binding sites and depression in dementia with Lewy bodies.
2002-05
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/6478739
2 mg for 3 weeks
Route of Administration: Oral
Name Type Language
cianopramine [INN]
Preferred Name English
CIANOPRAMINE
INN   MART.   WHO-DD  
INN  
Official Name English
RO 11-2464
Code English
CIANOPRAMINE [MART.]
Common Name English
5-(3-(DIMETHYLAMINO)PROPYL)-10,11-DIHYDRO-5H-DIBENZ(B,F)AZEPINE-3-CARBONITRILE
Systematic Name English
Cianopramine [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Wed Apr 02 06:59:36 GMT 2025 , Edited by admin on Wed Apr 02 06:59:36 GMT 2025
Code System Code Type Description
PUBCHEM
48126
Created by admin on Wed Apr 02 06:59:36 GMT 2025 , Edited by admin on Wed Apr 02 06:59:36 GMT 2025
PRIMARY
FDA UNII
02MNR4P2PM
Created by admin on Wed Apr 02 06:59:36 GMT 2025 , Edited by admin on Wed Apr 02 06:59:36 GMT 2025
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MESH
C024316
Created by admin on Wed Apr 02 06:59:36 GMT 2025 , Edited by admin on Wed Apr 02 06:59:36 GMT 2025
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NCI_THESAURUS
C80767
Created by admin on Wed Apr 02 06:59:36 GMT 2025 , Edited by admin on Wed Apr 02 06:59:36 GMT 2025
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EPA CompTox
DTXSID90216956
Created by admin on Wed Apr 02 06:59:36 GMT 2025 , Edited by admin on Wed Apr 02 06:59:36 GMT 2025
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EVMPD
SUB06227MIG
Created by admin on Wed Apr 02 06:59:36 GMT 2025 , Edited by admin on Wed Apr 02 06:59:36 GMT 2025
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SMS_ID
100000081881
Created by admin on Wed Apr 02 06:59:36 GMT 2025 , Edited by admin on Wed Apr 02 06:59:36 GMT 2025
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WIKIPEDIA
Cianopramine
Created by admin on Wed Apr 02 06:59:36 GMT 2025 , Edited by admin on Wed Apr 02 06:59:36 GMT 2025
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CAS
66834-24-0
Created by admin on Wed Apr 02 06:59:36 GMT 2025 , Edited by admin on Wed Apr 02 06:59:36 GMT 2025
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INN
5185
Created by admin on Wed Apr 02 06:59:36 GMT 2025 , Edited by admin on Wed Apr 02 06:59:36 GMT 2025
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ChEMBL
CHEMBL2106504
Created by admin on Wed Apr 02 06:59:36 GMT 2025 , Edited by admin on Wed Apr 02 06:59:36 GMT 2025
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