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Merck

R103

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:
87051-43-2
Molecular Weight:
477.57
NACRES:
NA.77
PubChem Substance ID:
24278117
UNSPSC Code:
12352200
MDL number:
MFCD00069341
Form:
powder
Quality level:
200

Key Documents

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form

powder

Quality Level

200

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

Gene Information

human ... HTR2A(3356)
rat ... Adra1a(29412), Drd2(24318), Htr1a(24473), Htr2a(29595), Htr7(65032)

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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000214592
0000214594
0000214595
0000214594
0000214592

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Depression-like behavior in the forced swimming test in PACAP-deficient mice: amelioration by the atypical antipsychotic risperidone
Hashimoto H, et al.
Journal of Neurochemistry, 110(2), 595-602 (2009)
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)
Xiaojun Jia et al.
Neuropharmacology, 62(2), 775-783 (2011-09-20)
The key role of the hypothalamic neuropeptides orexins in maintenance and promotion of arousal has been well established in normal mammalian animals, but whether orexins exert arousal effects under pathological condition such as coma was little studied. In this study
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)
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