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Details

Stereochemistry ACHIRAL
Molecular Formula C19H23N3.ClH
Molecular Weight 329.867
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BINEDALINE HYDROCHLORIDE

SMILES

Cl.CN(C)CCN(C)N1C=C(C2=C1C=CC=C2)C3=CC=CC=C3

InChI

InChIKey=LWSDQRSJVPCQRC-UHFFFAOYSA-N
InChI=1S/C19H23N3.ClH/c1-20(2)13-14-21(3)22-15-18(16-9-5-4-6-10-16)17-11-7-8-12-19(17)22;/h4-12,15H,13-14H2,1-3H3;1H

HIDE SMILES / InChI

Molecular Formula C19H23N3
Molecular Weight 293.406
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Binedaline is a drug that was investigated as an antidepressant in the 1980s. It`s development for the treatment of major depressive disorder was discontinued. It acts as a selective norepinephrine reuptake inhibitor (Ki = 25 nM), with relatively insignificant influence on the serotonin (Ki = 847 nM) and dopamine (Ki >= 2 µM) transporters.

CNS Activity

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
The effects of two single oral doses of binedaline (50 and 100 mg), imipramine (75 mg) and placebo were compared on a range of psychological tasks (logical reasoning, the Stroop test, and five-choice serial reaction) in healthy young volunteers.
Route of Administration: Oral
In Vitro Use Guide
Binedaline and desmethylbinedaline were potent inhibitors of the uptake of norepinephrine in synaptosomes from rat cerebral cortex (Ki = 25 and 29 nM, respectively). Binedaline also inhibited 5-HT uptake with a weak affinity (Ki = 847 nM) but was inactive as an inhibitor of dopamine uptake in synaptosomes from rat striatum (Ki greater than 2 uM).
Substance Class Chemical
Record UNII
WEK9FVT37G
Record Status Validated (UNII)
Record Version