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R103

Sigma-Aldrich

Ritanserin

powder

Synonym(s):

6-[2-[4-(bis(4-Fluorophenyl)methylene]-1-piperidinyl]ethyl]-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one

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About This Item

Empirical Formula (Hill Notation):
C27H25F2N3OS
CAS Number:
Molecular Weight:
477.57
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

form

powder

color

white

solubility

methanol: >10 mg/mL
DMSO: >10.1 mg/mL
2-hydroxypropyl-β-cyclodextrin: insoluble
H2O: insoluble
dilute aqueous base: insoluble

SMILES string

CC1=C(CCN2CCC(\CC2)=C(\c3ccc(F)cc3)c4ccc(F)cc4)C(=O)N5C=CSC5=N1

InChI

1S/C27H25F2N3OS/c1-18-24(26(33)32-16-17-34-27(32)30-18)12-15-31-13-10-21(11-14-31)25(19-2-6-22(28)7-3-19)20-4-8-23(29)9-5-20/h2-9,16-17H,10-15H2,1H3

InChI key

JUQLTPCYUFPYKE-UHFFFAOYSA-N

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Application

Ritanserin has been used in behavioral testing and as a serotonin 2A receptor (5-HT2A)-receptor antagonist.

Biochem/physiol Actions

Potent 5-HT2A serotonin receptor antagonist/inverse agonist that crosses the blood-brain barrier.
Ritanserin is a potent serotonin 2A receptor (5-HT2A) serotonin receptor antagonist/inverse agonist, which crosses the blood-brain barrier. It modulates 5-HT2A receptors and has been suggested to have antiparkinsonian effect. Ritanserin also impacts schizophrenia by modulating mood, cognition and negative symptoms.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Modulation by 5-HT2A receptors of aggressive behavior in isolated mice
Sakaue M, et al.
Japanese Journal of Pharmacology, 89(1), 89-92 (2002)
The 5-HT 2 antagonist ritanserin blocks dopamine re-uptake in the rat frontal cortex
Ruiu S, et al.
Molecular Psychiatry, 5(6), 673-673 (2000)
Does ritanserin, a potent serotonin-S2 antagonist, restore energetic functions during the night?
Janssen, PAJ
Journal of the Royal Society of Medicine, 80, 409-413 (1987)
Anna Sławińska et al.
Neuropharmacology, 66, 225-235 (2012-05-29)
Previous studies demonstrated that the Group III mGlu receptor-selective orthosteric agonist, LSP1-2111 produced anxiolytic- but not antidepressant-like effects upon peripheral administration. Herein, we report the pharmacological actions of Lu AF21934, a novel, selective, and brain-penetrant positive allosteric modulator (PAM) of
J E Leysen et al.
Molecular pharmacology, 27(6), 600-611 (1985-06-01)
In vitro and in vivo receptor-binding properties of the new serotonin antagonist, ritanserin, are reported. In in vitro binding assays, ritanserin shows high affinity binding to serotonin-S2 sites in rat frontal cortex tissue: IC50 = 0.9 nM without drug preincubation

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