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Details

Stereochemistry ACHIRAL
Molecular Formula C25H34N4O2
Molecular Weight 422.5631
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of WAY-100635

SMILES

COC1=C(C=CC=C1)N2CCN(CCN(C(=O)C3CCCCC3)C4=NC=CC=C4)CC2

InChI

InChIKey=SBPRIAGPYFYCRT-UHFFFAOYSA-N
InChI=1S/C25H34N4O2/c1-31-23-12-6-5-11-22(23)28-18-15-27(16-19-28)17-20-29(24-13-7-8-14-26-24)25(30)21-9-3-2-4-10-21/h5-8,11-14,21H,2-4,9-10,15-20H2,1H3

HIDE SMILES / InChI

Molecular Formula C25H34N4O2
Molecular Weight 422.5631
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16915381 | https://www.ncbi.nlm.nih.gov/pubmed/8566121 | https://www.ncbi.nlm.nih.gov/pubmed/8768719 | http://link.springer.com/chapter/10.1007%2F978-94-011-0429-6_9

WAY-100635 is an achiral phenylpiperazine derivative that originally discovered as an antagotist of 5-HT1A receptor. Later WAY-100635 was described as a potent dopamine D4 receptor agonist. WAY-100635 was in preclinical studies for the treatment of Diabetes mellitus, Anxiety and Cognition disorders, howevere the development was discontinued. Isotope labeled WAY-100635 could be used for the study of central 5-HT 1A receptors with potential for application to the study of neuropsychiatric disorders and to the human pharmacology of psychoactive drugs.

CNS Activity

Curator's Comment: WAY-100635 is CNS active in animals. Isotope labeled WAY-100635 could be used for the qualitative and quantitative study of 5-HT1A receptors in the human brain.

Approval Year

PubMed

PubMed

TitleDatePubMed
Mirtazapine increases dopamine release in prefrontal cortex by 5-HT1A receptor activation.
2004 Apr 30
Effects of the 5-HT7 receptor antagonists SB-269970 and DR 4004 in autoshaping Pavlovian/instrumental learning task.
2004 Dec 6
WAY100635 and female rat lordosis behavior.
2004 Jul 9
Acute treatment with the antidepressant fluoxetine internalizes 5-HT1A autoreceptors and reduces the in vivo binding of the PET radioligand [18F]MPPF in the nucleus raphe dorsalis of rat.
2004 Jun 9
The hypotensive effect of BMY 7378 involves central 5-HT1A receptor stimulation in the adult but not in the young rat.
2004 Nov-Dec
Cloned human 5-HT1A receptor pharmacology determined using agonist binding and measurement of cAMP accumulation.
2004 Oct
Novel antipsychotic agents with 5-HT(1A) agonist properties: role of 5-HT(1A) receptor activation in attenuation of catalepsy induction in rats.
2005 Aug
Anticataleptic properties of alpha2 adrenergic antagonists in the crossed leg position and bar tests: differential mediation by 5-HT1A receptor activation.
2005 Feb
N-oxide analogs of WAY-100635: new high affinity 5-HT(1A) receptor antagonists.
2005 Feb 1
Citalopram combined with WAY 100635 inhibits ejaculation and ejaculation-related Fos immunoreactivity.
2005 Feb 10
In vitro profile of the antidepressant candidate OPC-14523 at rat and human 5-HT1A receptors.
2005 Jul 11
Dopamine uptake inhibitor-induced rotation in 6-hydroxydopamine-lesioned rats involves both D1 and D2 receptors but is modulated through 5-hydroxytryptamine and noradrenaline receptors.
2005 Mar
Serotonin1A-receptor antagonism blocks psychostimulant properties of diethylpropion in marmosets (Callithrix penicillata).
2005 Mar 21
Role of 5-HT1A and 5-HT1B receptors in the antinociceptive effect of tramadol.
2005 Mar 21
Repeated administration of citalopram and imipramine alters the responsiveness of rat hippocampal circuitry to the activation of 5-HT7 receptors.
2005 Nov 7
Differential effects of the 5-hydroxytryptamine (5-HT)1A receptor inverse agonists Rec 27/0224 and Rec 27/0074 on electrophysiological responses to 5-HT1A receptor activation in rat dorsal raphe nucleus and hippocampus in vitro.
2005 Oct
Inhibition of serotonergic neurons in the nucleus paragigantocellularis lateralis fragments sleep and decreases rapid eye movement sleep in the piglet: implications for sudden infant death syndrome.
2005 Sep 7
WAY-100635 antagonist-induced plasticity of 5-HT receptors: regulatory differences between a stable cell line and an in vivo native system.
2006 Jul
Anticonvulsant effect of the selective 5-HT1B receptor agonist CP 94253 in mice.
2006 Jul 10
MDMA and fenfluramine reduce L-DOPA-induced dyskinesia via indirect 5-HT1A receptor stimulation.
2006 May
Clozapine modulates aromatic L-amino acid decarboxylase activity in mouse striatum.
2006 May
Early life blockade of 5-hydroxytryptamine 1A receptors normalizes sleep and depression-like behavior in adult knock-out mice lacking the serotonin transporter.
2006 May 17
Serotonin receptor involvement in effects of restraint on female rat lordosis behavior.
2007 Apr
Role of peripheral 5-HT1A receptors in detrusor over activity associated with partial bladder outlet obstruction in female rats.
2007 Apr 30
The partial 5-HT(1A) agonist buspirone reduces the expression and development of l-DOPA-induced dyskinesia in rats and improves l-DOPA efficacy.
2007 Aug-Sep
Substance P neurokinin 1 receptor activation within the dorsal raphe nucleus controls serotonin release in the mouse frontal cortex.
2007 Dec
5-HT1A receptors mediate (+)8-OH-DPAT-stimulation of extracellular signal-regulated kinase (MAP kinase) in vivo in rat hypothalamus: time dependence and regional differences.
2007 Dec 5
Acetaminophen recruits spinal p42/p44 MAPKs and GH/IGF-1 receptors to produce analgesia via the serotonergic system.
2007 Feb
Dopamine released from 5-HT terminals is the cause of L-DOPA-induced dyskinesia in parkinsonian rats.
2007 Jul
Antagonist-induced increase in 5-HT1A-receptor expression in adult rat hippocampus and cortex.
2007 Jul
Single exposure to a serotonin 1A receptor agonist, (+)8-hydroxy-2-(di-n-propylamino)-tetralin, produces a prolonged heterologous desensitization of serotonin 2A receptors in neuroendocrine neurons in vivo.
2007 Mar
Role of postsynaptic serotonin1A receptors in risperidone-induced increase in acetylcholine release in rat prefrontal cortex.
2007 Mar 22
3,4-Methylenedioxymethamphetamine- and 8-hydroxy-2-di-n-propylamino-tetralin-induced hypothermia: role and location of 5-hydroxytryptamine 1A receptors.
2007 Nov
Effects of repetitive administration of tianeptine, zinc hydroaspartate and electroconvulsive shock on the reactivity of 5-HT(7) receptors in rat hippocampus.
2007 Nov-Dec
Descending facilitation of spinal NMDA-dependent reflex potentiation from pontine tegmentum in rats.
2007 Oct
Distinct electrophysiological effects of paliperidone and risperidone on the firing activity of rat serotonin and norepinephrine neurons.
2007 Sep
Effects of 5-HT drugs in prefrontal cortex during memory formation and the ketamine amnesia-model.
2008
Serotonin activates presynaptic and postsynaptic receptors in rat globus pallidus.
2008 Apr
Fluoxetine-induced proliferation and differentiation of neural progenitor cells isolated from rat postnatal cerebellum.
2008 Aug 1
Stress-induced hyperthermia and basal body temperature are mediated by different 5-HT(1A) receptor populations: a study in SERT knockout rats.
2008 Aug 20
Antipsychotics differ in their ability to internalise human dopamine D2S and human serotonin 5-HT1A receptors in HEK293 cells.
2008 Feb 26
Delta(9)-tetrahydrocannabinol prolongs the immobility time in the mouse forced swim test: involvement of cannabinoid CB(1) receptor and serotonergic system.
2008 Jul 28
Involvement of glutamate neurotransmission and N-methyl-d-aspartate receptor in the activation of midbrain dopamine neurons by 5-HT1A receptor agonists: an electrophysiological study in the rat.
2008 Oct 28
Inhibition of monoamine oxidases desensitizes 5-HT1A autoreceptors and allows nicotine to induce a neurochemical and behavioral sensitization.
2009 Jan 28
Activation of serotonin 5-HT1-receptors decreased gripping-induced immobility episodes in taiep rats.
2009 Jan 9
The role of the dorsal raphe nucleus in the development, expression, and treatment of L-dopa-induced dyskinesia in hemiparkinsonian rats.
2009 Jul
The sigma-1 antagonist BMY-14802 inhibits L-DOPA-induced abnormal involuntary movements by a WAY-100635-sensitive mechanism.
2009 Jul
Contribution of the striatum to the effects of 5-HT1A receptor stimulation in L-DOPA-treated hemiparkinsonian rats.
2009 May 15
Differential effects of M1 and 5-hydroxytryptamine1A receptors on atypical antipsychotic drug-induced dopamine efflux in the medial prefrontal cortex.
2009 Sep
The firing activity of pyramidal neurons in medial prefrontal cortex and their response to 5-hydroxytryptamine-1A receptor stimulation in a rat model of Parkinson's disease.
2009 Sep 15
Patents

Sample Use Guides

mice: 3.0 mg/kg, i.p. rats: 200 ng, injected in the median raphé nucleus cats: 0.025-0.5 mg/kg i.v.
Route of Administration: Other
Exposure of h5-HT(1A) CHO cells to WAY-100635 decreased the cell-surface h5-HT(1A) receptor density in a way that was both time (24-72 h) and concentration (1-100 nM) dependent. In dorsal raphe nucleus slices superfused with WAY 100635 (10 nM), the majority of putative 5-HT neurons increased their firing rate. In addition, WAY 100635 completely prevented the decrease in firing rate produced by 5-HT (3-15 microM), 8-OH-DPAT (10 nM), 5-carboxamidotryptamine (20 nM) and lesopitron (100 nM).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:08:29 UTC 2023
Edited
by admin
on Fri Dec 15 15:08:29 UTC 2023
Record UNII
71IH826FEG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
WAY-100635
Common Name English
CYCLOHEXANECARBOXAMIDE, N-(2-(4-(2-METHOXYPHENYL)-1-PIPERAZINYL)ETHYL)-N-2-PYRIDINYL-
Systematic Name English
Code System Code Type Description
WIKIPEDIA
WAY 100635
Created by admin on Fri Dec 15 15:08:29 UTC 2023 , Edited by admin on Fri Dec 15 15:08:29 UTC 2023
PRIMARY
FDA UNII
71IH826FEG
Created by admin on Fri Dec 15 15:08:29 UTC 2023 , Edited by admin on Fri Dec 15 15:08:29 UTC 2023
PRIMARY
PUBCHEM
5684
Created by admin on Fri Dec 15 15:08:29 UTC 2023 , Edited by admin on Fri Dec 15 15:08:29 UTC 2023
PRIMARY
CAS
162760-96-5
Created by admin on Fri Dec 15 15:08:29 UTC 2023 , Edited by admin on Fri Dec 15 15:08:29 UTC 2023
PRIMARY
EPA CompTox
DTXSID20167467
Created by admin on Fri Dec 15 15:08:29 UTC 2023 , Edited by admin on Fri Dec 15 15:08:29 UTC 2023
PRIMARY
MESH
C090413
Created by admin on Fri Dec 15 15:08:29 UTC 2023 , Edited by admin on Fri Dec 15 15:08:29 UTC 2023
PRIMARY
Related Record Type Details
LABELED -> NON-LABELED
LABELED -> NON-LABELED
TARGET -> AGONIST
Kd
TARGET -> INHIBITOR
Exhibited antagonism activity at both presynaptic and postsynaptic 5-HT1A receptor sites.
Kd