WAY-208466

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H18FN3O2S
Molecular Weight	347.407
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCN1C=C(C2=CC=CN=C12)S(=O)(=O)C3=CC(F)=CC=C3

InChI

InChIKey=SFSFIDVAEMDPIP-UHFFFAOYSA-N

InChI=1S/C17H18FN3O2S/c1-20(2)9-10-21-12-16(15-7-4-8-19-17(15)21)24(22,23)14-6-3-5-13(18)11-14/h3-8,11-12H,9-10H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C17H18FN3O2S
Molecular Weight	347.407
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/17625499
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/20217056 | https://www.ncbi.nlm.nih.gov/pubmed/23624323

WAY 208466 dihydrochloride is a high affinity, selective SR-6 (5-HT6) receptor agonist. WAY-208466 produced both antidepressant-like and anxiolytic-like effects. Direct infusion of WAY-208466 into the dorsal raphe nucleus, locus coeruleus, basal forebrain (horizontal limb of the diagonal band of Broca) or laterodorsal tegmental nucleus specifically decreased REM sleep without significantly altering wakefulness or slow wave sleep.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 6 (5-HT6) receptor 45 Target ID: CHEMBL3371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17625499	Agonist 2678	4.8 nM [Ki]
Serotonin 2c (5-HT2c) receptor 124 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17625499	Antagonist 2778	217.0 nM [Ki]
Serotonin 2c (5-HT2c) receptor 124 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17625499	Agonist 2678	644.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20217056	Primary		Preclinical	Unknown Approved Use Unknown
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20217056	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Neuropharmacological profile of novel and selective 5-HT6 receptor agonists: WAY-181187 and WAY-208466.	2008 May	17625499
Antidepressant and anxiolytic effects of selective 5-HT6 receptor agonists in rats.	2011 Feb	20217056
Serotonin₆ receptors in the dorsal hippocampus regulate depressive-like behaviors in unilateral 6-hydroxydopamine-lesioned Parkinson's rats.	2015 Aug	25863121
WAY208466 inhibits glutamate release at hippocampal nerve terminals.	2016 Jun 15	27068148

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 10 mg/kg once a day

Route of Administration: Other

In Vitro Use Guide

In the presence of DL-TBOA, WAY208466 (30 uM) effectively caused an average inhibition of 35 % of 4-aminopyridine-evoked glutamate release; the inhibition was similar to that produced by WAY208466 alone (41%).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 12:09:11 UTC 2023` Edited by `admin` on `Sat Dec 16 12:09:11 UTC 2023`
Record UNII	0AXW9ALG9W
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

WAY-208466

Common Name

English

WAY-208,466

Code

English

3-((3-FLUOROPHENYL)SULFONYL)-N,N-DIMETHYL-1H-PYRROLO(2,3-B)PYRIDINE-1-ETHANAMINE

Systematic Name

English

1H-PYRROLO(2,3-B)PYRIDINE-1-ETHANAMINE, 3-((3-FLUOROPHENYL)SULFONYL)-N,N-DIMETHYL-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID60621755