BINEDALINE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H23N3
Molecular Weight	293.406
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=SXYFFMXPDDGOEK-UHFFFAOYSA-N

InChI=1S/C19H23N3/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

HIDE SMILES / InChI

Molecular Formula	C19H23N3
Molecular Weight	293.406
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2540319 | https://adisinsight.springer.com/drugs/800000676 | https://www.ncbi.nlm.nih.gov/pubmed/6239991

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

Title	Date	PubMed
Pharmacological profile of binedaline, a new antidepressant drug.	1989-04	2540319
Binedaline binding to plasma proteins and red blood cells in humans.	1985-07	4032243
A controlled double-blind study comparing binedaline and imipramine in the treatment of endogenous depression.	1984	6239991

Patents

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 Created by `admin` on `Mon Mar 31 18:02:04 GMT 2025` Edited by `admin` on `Mon Mar 31 18:02:04 GMT 2025`
Record UNII	3AVG9P140R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BINEDALINE [MI]

Preferred Name

English

BINEDALINE

Official Name

English

binedaline [INN]

Common Name

English

1-((2-(DIMETHYLAMINO)ETHYL)METHYLAMINO)-3-PHENYLINDOLE

Systematic Name

English

BINEDALINE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265