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
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
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.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Selective alterations of the CB1 receptors and the fatty acid amide hydrolase in the ventral striatum of alcoholics and suicides. | 2010-07 |
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| Determination of moxifloxacin in human plasma, plasma ultrafiltrate, and cerebrospinal fluid by a rapid and simple liquid chromatography- tandem mass spectrometry method. | 2010-04 |
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| Differential regulation of serotonin-1A receptor-stimulated [35S]GTP gamma S binding in the dorsal raphe nucleus by citalopram and escitalopram. | 2008-03-31 |
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| Architectonic distribution of the serotonin transporter within the orbitofrontal cortex of the vervet monkey. | 2007-09-21 |
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| Serotonin transporter function, but not expression, is dependent on brain-derived neurotrophic factor (BDNF): in vivo studies in BDNF-deficient mice. | 2007-05 |
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| 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
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3382461
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/6478739
2 mg for 3 weeks
Route of Administration:
Oral
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NCI_THESAURUS |
C66885
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48126
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C024316
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C80767
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DTXSID90216956
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Cianopramine
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66834-24-0
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5185
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CHEMBL2106504
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ACTIVE MOIETY