DU-24565

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H14N4O2
Molecular Weight	258.2759
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+](=O)C1=CC=C2N=C(C=CC2=C1)N3CCNCC3

InChI

InChIKey=GGDBEAVVGFNWIA-UHFFFAOYSA-N

InChI=1S/C13H14N4O2/c18-17(19)11-2-3-12-10(9-11)1-4-13(15-12)16-7-5-14-6-8-16/h1-4,9,14H,5-8H2

HIDE SMILES / InChI

Molecular Formula	C13H14N4O2
Molecular Weight	258.2759
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/6973481 | https://www.ncbi.nlm.nih.gov/pubmed/3110297 | https://www.ncbi.nlm.nih.gov/pubmed/7776439

Du-24565 is a potent and selective inhibitor of the synaptosomal uptake of serotonin. At higher concentration, it affects the uptake of norepinephrine and dopamine. It is a potential antidepressant and can be useful as a pharmacological tool to study the role of 5-HT in the central nervous system. DU-24565 had little effect on serotonin or tyrosine accumulation in human melanoma cells but suppressed the uptake of extracellular Dopa. In vitro, DU-24565 inhibited the proliferation of PC-3, DU-145 and LNCaP human prostate carcinoma cells in a dose-dependent manner.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
serotonin uptake 20 Target ID: GO:0051610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6973481	Inhibitor 8297	0.045 µM [IC50]
norepinephrine uptake 18 Target ID: GO:0051620 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6973481	Inhibitor 8297	66.0 µM [IC50]
dopamine uptake 14 Target ID: GO:0090494 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6973481	Inhibitor 8297	41.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7776439	Primary		Basic research	Unknown Approved Use Unknown
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15723351 https://www.ncbi.nlm.nih.gov/pubmed/6973481	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synthesis of a fluorine-18-labelled derivative of 6-nitroquipazine, as a radioligand for the in vivo serotonin transporter imaging with PET.	2002 Aug	12057650
Synthesis, radiolabeling and preliminary biological evaluation of radiolabeled 5-methyl-6-nitroquipazine, a potential radioligand for the serotonin transporter.	2002 Dec 16	12443787
Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 2: 4-substituted 6-nitroquipazines.	2002 Mar 11	11859009
Biochemical evidence for the presence of serotonin transporters in the rat cochlea.	2003 Aug	12948600
Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter: Part 3. A potential 5-HT transporter imaging agent, 3-(3-[18F]fluoropropyl)-6-nitroquipazine.	2003 Nov 17	14604657
Zinc modulation of serotonin uptake in the adult rat corpus callosum.	2005 Apr 1	15723351
Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 4: 3-Alkyl-4-halo-6-nitroquipazines.	2005 Aug 15	15993088
Extracellular protons differentially potentiate the responses of native AMPA receptor subtypes regulating neurotransmitter release.	2005 Jan	15665865
Design and synthesis of long-chain arylpiperazines with mixed affinity for serotonin transporter (SERT) and 5-HT(1A) receptor.	2005 Oct	16259761
Presynaptic serotonergic modulation of 5-HT and acetylcholine release in the hippocampus and the cortex of 5-HT1B-receptor knockout mice.	2006 Jun 15	16750486
Presynaptic modulation of 5-HT release in the rat septal region.	2007 May 11	17383104
Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 5: 2'-Substituted 6-nitroquipazines.	2007 May 15	17376695
Synthesis and biological evaluation of one novel technetium-99m-labeled nitroquipazine derivative as an imaging agent for serotonin transporter.	2008 Dec	18684634
Effects of serotonergic agents on survival and hemolymph composition of the larval mosquito Aedes aegypti (Diptera: Culicidae, L.) in vivo: does serotonin regulate hemolymph acid-base homeostasis?	2009 Nov	19880735
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.	2009 Oct 23	19725810

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 1 mg/kg

Route of Administration: Oral

In Vitro Use Guide

DU-24565 at concentrations of 10(-8) and 10(-9) M was a potent inhibitor of serotonin uptake by rat blood platelets.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:46:40 UTC 2023` Edited by `admin` on `Fri Dec 15 17:46:40 UTC 2023`
Record UNII	28M0X094BH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DU-24565

Common Name

English

6-NITRO-2-PIPERAZIN-1-YL-QUINOLINE

Systematic Name

English

Code System Code Type Description

FDA UNII

28M0X094BH