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W108

Sigma-Aldrich

WAY-100635 maleate salt

powder

Synonym(s):

N-[2-[4-(2-Methoxyphenyl)-1-piperazinyl]ethyl]-N-2-pyridinylcyclohexanecarboxamide maleate salt

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About This Item

Empirical Formula (Hill Notation):
C25H34N4O2 · C4H4O4
CAS Number:
634908-75-1
Molecular Weight:
538.64
MDL number:
MFCD01321056
UNSPSC Code:
12352200
PubChem Substance ID:
24278113
NACRES:
NA.77

form

powder

Quality Level

100

color

white

solubility

H2O: 25 mg/mL

SMILES string

[H]\C(=C(/[H])C(O)=O)C(O)=O.COc1ccccc1N2CCN(CC2)CCN(C(=O)C3CCCCC3)c4ccccn4

InChI

1S/C25H34N4O2.C4H4O4/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;5-3(6)1-2-4(7)8/h5-8,11-14,21H,2-4,9-10,15-20H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

InChI key

XIGAHNVCEFUYOV-BTJKTKAUSA-N

Gene Information

human ... HTR1A(3350)

Application

WAY-100635 maleate salt has been used as a 5-HT1A serotonin receptor antagonist:
  • to study whether the behavior of the cleaner wrasse is regulated by serotonin activity
  • to block activity of 3,4 methylenedioxymethamphetamine (MDMA) used to induce oxytocin release in male Wistar rats to increase their social behavior
  • to study the role of serotonin during metamorphosis of the ascidian Phallusia mammillata larvae

Biochem/physiol Actions

WAY-100635 maleate salt is a highly selective 5-HT1A serotonin receptor antagonist. It has an ability to inhibit brexpiprazole, an antipsychotic drug that regulates serotonin-dopamine activity.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Effects of brexpiprazole, a novel serotonin-dopamine activity modulator, on phencyclidine-induced cognitive deficits in mice: a role for serotonin 5-HT1A receptors
Yoshimi N, et al.
Pharmacology, Biochemistry, and Behavior, 124, 245-249 (2014)
E A Forster et al.
European journal of pharmacology, 281(1), 81-88 (1995-07-25)
WAY-100635 (N-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-N-(2- pyridinyl)cyclohexanecarboxamide trihydrochloride) is an achiral phenylpiperazine derivative that binds with high affinity and selectivity to the 5-HT1A receptor. WAY-100635 displaced specific binding of the 5-HT1A radioligand, [3H]8-OH-DPAT (8-hydroxy-2-(di-n-propylamino)tetralin), to rat hippocampal membranes with a pIC50 of 8.87. This
Dopamine and serotonin modulate the onset of metamorphosis in the ascidian Phallusia mammillata
Zega G, et al.
Developmental Biology, 282(1), 246-256 (2005)
Naozumi Araragi et al.
Frontiers in pharmacology, 4, 97-97 (2013-08-13)
Firing activity of serotonin (5-HT) neurons in the dorsal raphe nucleus (DRN) is controlled by inhibitory somatodendritic 5-HT1A autoreceptors. This autoinhibitory mechanism is implicated in the etiology of disorders of emotion regulation, such as anxiety disorders and depression, as well
H Gozlan et al.
European journal of pharmacology, 288(2), 173-186 (1995-01-16)
The tritiated derivative of the novel silent 5-HT1A receptor antagonist WAY 100635 [N-(2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl)-N-(2-pyridinyl) cyclohexane carboxamide] was tested as a potential radioligand of 5-HT1A receptors in the rat brain. Binding assays with membranes from various brain regions showed that [3H]WAY 100635
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