INDALPINE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H20N2
Molecular Weight	228.3327
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(CC1=CNC2=C1C=CC=C2)C3CCNCC3

InChI

InChIKey=SADQVAVFGNTEOD-UHFFFAOYSA-N

InChI=1S/C15H20N2/c1-2-4-15-14(3-1)13(11-17-15)6-5-12-7-9-16-10-8-12/h1-4,11-12,16-17H,5-10H2

HIDE SMILES / InChI

Molecular Formula	C15H20N2
Molecular Weight	228.3327
Charge	0
Count

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

Description
Sources: https://www.drugbank.ca/drugs/DB08953 | https://www.ncbi.nlm.nih.gov/pubmed/6151492 | https://www.ncbi.nlm.nih.gov/pubmed/6255361

Indalpine was one of the first selective serotonin reuptake inhibitors to reach the American market. It was initially marketed by Pharmuka. Indalpine was used in the treatment of depression and anxiety. However, after the emergence of widespread concern regarding adverse effects caused by SSRIs, and reported hematological effects caused by Indalpine, it was abruptly withdrawn from the US market. Indalpine also showed analgesic properties in the hot plate test in mice. It enhanced the analgesic effect of morphine and pethidine.

Originator

Approval Year

PubMed

Title	Date	PubMed
Synthesis and hSERT activity of homotryptamine analogs. Part 6: [3+2] dipolar cycloaddition of 3-vinylindoles.	2010-02-01	20034793
Effects of autoshaping procedures on 3H-8-OH-DPAT-labeled 5-HT1a binding and 125I-LSD-labeled 5-HT2a binding in rat brain.	2003-06-13	12763605
Studies toward the discovery of the next generation of antidepressants. Part 2: incorporating a 5-HT(1A) antagonist component into a class of serotonin reuptake inhibitors.	2002-02-11	11814784
[Hematologic toxicity of antidepressive agents].	1988-07-01	3058454

Patents

Sample Use Guides

In Vivo Use Guide

Indalpine 150 mg per day and mianserin 60 mg per day were compared in a double-blind study of 65 depressed out-patients: 52 patients completed the 4-week trial.

Route of Administration: Oral

In Vitro Use Guide

The binding of [3H]indalpine (4-[2-(3-indolyl)]ethyl piperidine) to slide-mounted sections of rat brain has been characterized. This 5-hydroxytryptamine (5-HT) uptake blocker binds to sections with high affinity (KD approximately 1 nM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:43:21 GMT 2025` Edited by `admin` on `Mon Mar 31 21:43:21 GMT 2025`
Record UNII	V35562QSVT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INDALPINE [MI]

Preferred Name

English

INDALPINE

Official Name

English

indalpine [INN]

Common Name

English

3-(2-(4-PIPERIDYL)ETHYL)INDOLE

Systematic Name

English

Indalpine [WHO-DD]

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL276520