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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=C(CCC3=C1C=C(C=C3)C#N)C=CC=C2

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

Molecular Formula C20H23N3
Molecular Weight 305.4167
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Serotonin transporter function, but not expression, is dependent on brain-derived neurotrophic factor (BDNF): in vivo studies in BDNF-deficient mice.
2007 May
Architectonic distribution of the serotonin transporter within the orbitofrontal cortex of the vervet monkey.
2007 Sep 21
Differential regulation of serotonin-1A receptor-stimulated [35S]GTP gamma S binding in the dorsal raphe nucleus by citalopram and escitalopram.
2008 Mar 31
Determination of moxifloxacin in human plasma, plasma ultrafiltrate, and cerebrospinal fluid by a rapid and simple liquid chromatography- tandem mass spectrometry method.
2010 Apr
Selective alterations of the CB1 receptors and the fatty acid amide hydrolase in the ventral striatum of alcoholics and suicides.
2010 Jul
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:59:23 GMT 2023
Edited
by admin
on Sat Dec 16 15:59:23 GMT 2023
Record UNII
02MNR4P2PM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIANOPRAMINE
INN   MART.   WHO-DD  
INN  
Official Name English
RO 11-2464
Code English
CIANOPRAMINE [MART.]
Common Name English
cianopramine [INN]
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 Sat Dec 16 15:59:23 GMT 2023 , Edited by admin on Sat Dec 16 15:59:23 GMT 2023
Code System Code Type Description
PUBCHEM
48126
Created by admin on Sat Dec 16 15:59:23 GMT 2023 , Edited by admin on Sat Dec 16 15:59:23 GMT 2023
PRIMARY
FDA UNII
02MNR4P2PM
Created by admin on Sat Dec 16 15:59:23 GMT 2023 , Edited by admin on Sat Dec 16 15:59:23 GMT 2023
PRIMARY
MESH
C024316
Created by admin on Sat Dec 16 15:59:23 GMT 2023 , Edited by admin on Sat Dec 16 15:59:23 GMT 2023
PRIMARY
NCI_THESAURUS
C80767
Created by admin on Sat Dec 16 15:59:23 GMT 2023 , Edited by admin on Sat Dec 16 15:59:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID90216956
Created by admin on Sat Dec 16 15:59:23 GMT 2023 , Edited by admin on Sat Dec 16 15:59:23 GMT 2023
PRIMARY
EVMPD
SUB06227MIG
Created by admin on Sat Dec 16 15:59:23 GMT 2023 , Edited by admin on Sat Dec 16 15:59:23 GMT 2023
PRIMARY
SMS_ID
100000081881
Created by admin on Sat Dec 16 15:59:23 GMT 2023 , Edited by admin on Sat Dec 16 15:59:23 GMT 2023
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WIKIPEDIA
Cianopramine
Created by admin on Sat Dec 16 15:59:23 GMT 2023 , Edited by admin on Sat Dec 16 15:59:23 GMT 2023
PRIMARY
CAS
66834-24-0
Created by admin on Sat Dec 16 15:59:23 GMT 2023 , Edited by admin on Sat Dec 16 15:59:23 GMT 2023
PRIMARY
INN
5185
Created by admin on Sat Dec 16 15:59:23 GMT 2023 , Edited by admin on Sat Dec 16 15:59:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106504
Created by admin on Sat Dec 16 15:59:23 GMT 2023 , Edited by admin on Sat Dec 16 15:59:23 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY