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

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

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.

Approval Year

PubMed

PubMed

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

Sample Use Guides

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 19:16:58 GMT 2025
Edited
by admin
on Mon Mar 31 19:16:58 GMT 2025
Record UNII
WEK9FVT37G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IXPRIM
Preferred Name English
BINEDALINE HYDROCHLORIDE
MI  
Common Name English
DIMETHYL-(2-(METHYL-(3-PHENYLINDOL-1-YL)AMINO)ETHYL)AZANIUM CHLORIDE
Systematic Name English
N,N,N'-TRIMETHYL-N'-(3-PHENYL-1H-INDOL-1-YL)ETHYLENEDIAMINE MONOHYDROCHLORIDE
Systematic Name English
INDOLE, 1-((2-(DIMETHYLAMINO)ETHYL)METHYLAMINO)-3-PHENYL-, HYDROCHLORIDE
Systematic Name English
RU-39780
Code English
BINEDALINE HYDROCHLORIDE [MI]
Common Name English
Code System Code Type Description
MERCK INDEX
m84
Created by admin on Mon Mar 31 19:16:58 GMT 2025 , Edited by admin on Mon Mar 31 19:16:58 GMT 2025
PRIMARY Merck Index
EVMPD
SUB25841
Created by admin on Mon Mar 31 19:16:58 GMT 2025 , Edited by admin on Mon Mar 31 19:16:58 GMT 2025
PRIMARY
SMS_ID
100000089669
Created by admin on Mon Mar 31 19:16:58 GMT 2025 , Edited by admin on Mon Mar 31 19:16:58 GMT 2025
PRIMARY
CAS
57647-35-5
Created by admin on Mon Mar 31 19:16:58 GMT 2025 , Edited by admin on Mon Mar 31 19:16:58 GMT 2025
PRIMARY
ECHA (EC/EINECS)
260-877-2
Created by admin on Mon Mar 31 19:16:58 GMT 2025 , Edited by admin on Mon Mar 31 19:16:58 GMT 2025
PRIMARY
EPA CompTox
DTXSID50973230
Created by admin on Mon Mar 31 19:16:58 GMT 2025 , Edited by admin on Mon Mar 31 19:16:58 GMT 2025
PRIMARY
PUBCHEM
42509
Created by admin on Mon Mar 31 19:16:58 GMT 2025 , Edited by admin on Mon Mar 31 19:16:58 GMT 2025
PRIMARY
FDA UNII
WEK9FVT37G
Created by admin on Mon Mar 31 19:16:58 GMT 2025 , Edited by admin on Mon Mar 31 19:16:58 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY