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=C1N=CC=C2)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 44 Target ID: CHEMBL3371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17625499	Agonist 2752	4.8 nM [Ki]
Serotonin 2c (5-HT2c) receptor 131 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17625499	Antagonist 2849	217.0 nM [Ki]
Serotonin 2c (5-HT2c) receptor 131 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17625499	Agonist 2752	644.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 275 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20217056	Primary		Preclinical	Unknown Approved Use Unknown
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20217056	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
WAY208466 inhibits glutamate release at hippocampal nerve terminals.	2016-06-15	27068148
Serotonin₆ receptors in the dorsal hippocampus regulate depressive-like behaviors in unilateral 6-hydroxydopamine-lesioned Parkinson's rats.	2015-08	25863121
The effects of systemic and local microinjection into the central nervous system of the selective serotonin 5-HT6 receptor agonist WAY-208466 on sleep and wakefulness in the rat.	2013-07-15	23624323
Antidepressant and anxiolytic effects of selective 5-HT6 receptor agonists in rats.	2011-02	20217056
Neuropharmacological profile of novel and selective 5-HT6 receptor agonists: WAY-181187 and WAY-208466.	2008-05	17625499

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 `Tue Apr 01 18:29:00 GMT 2025` Edited by `admin` on `Tue Apr 01 18:29:00 GMT 2025`
Record UNII	0AXW9ALG9W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

WAY-208,466

Preferred Name

English

WAY-208466

Common Name

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