INDATRALINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H15Cl2N
Molecular Weight	292.203
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN[C@@H]1C[C@H](C2=CC=CC=C12)C3=CC=C(Cl)C(Cl)=C3

InChI

InChIKey=SVFXPTLYMIXFRX-XJKSGUPXSA-N

InChI=1S/C16H15Cl2N/c1-19-16-9-13(11-4-2-3-5-12(11)16)10-6-7-14(17)15(18)8-10/h2-8,13,16,19H,9H2,1H3/t13-,16+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C16H15Cl2N
Molecular Weight	292.203
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10490887 | https://www.ncbi.nlm.nih.gov/pubmed/11889495 | https://www.ncbi.nlm.nih.gov/pubmed/22075572

Indatraline (Lu 19-005) is a non-selective monoamine transporter inhibitor that has been shown to block the reuptake of dopamine, norepinephrine, and serotonin with effects similar to those of cocaine. In vivo, indatraline produced behavioral effects suggestive of enhanced dopaminergic, noradrenergic, and serotonergic activity in mice. Indatraline also substituted for a high dose of cocaine in rats trained to discriminate between a low and a high dose of cocaine, which demonstrates that indatraline produces cocaine-like discriminative stimulus effects. Indatraline has been studied to block the action of methamphetamine and MDMA.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine transporter 180 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11150168	Inhibitor 8297	290.0 nM [Ki]
Serotonin transporter 178 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11150168	Inhibitor 8297	38.0 nM [Ki]
Norepinephrine transporter 191 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11150168	Inhibitor 8297	600.0 nM [Ki]

PubMed

Title	Date	PubMed
Pharmacology in vivo of the phenylindan derivative, Lu 19-005, a new potent inhibitor of dopamine, noradrenaline and 5-hydroxytryptamine uptake in rat brain.	1985 Apr	2409454
Effects of the long-acting monoamine reuptake inhibitor indatraline on cocaine self-administration in rhesus monkeys.	1999 Oct	10490887
Effects of indatraline and buprenorphine on self-administration of speedball combinations of cocaine and heroin by rhesus monkeys.	2001 Jul	11377924
Rhesus monkey trace amine-associated receptor 1 signaling: enhancement by monoamine transporters and attenuation by the D2 autoreceptor in vitro.	2007 Apr	17234900

Patents

Sample Use Guides

In Vivo Use Guide

rhesus monkeys: 0.1–0.56 mg/kg/day

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 15:51:09 GMT 2023` Edited by `admin` on `Sat Dec 16 15:51:09 GMT 2023`
Record UNII	4U40Y96J1Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INDATRALINE

Official Name

English

indatraline [INN]

Common Name

English

(±)-TRANS-3-(3,4-DICHLOROPHENYL)-N-METHYL-1-INDANAMINE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C94725