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Key Documents

C6848

Sigma-Aldrich

Ciproxifan maleate

≥98% (HPLC), powder

Sinonimo/i:

Cyclopropyl (4-[3-(1H-imidazol-4-yl)propyloxy]phenyl) ketone maleate salt, FUB 359 maleate salt

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About This Item

Formula empirica (notazione di Hill):
C16H18N2O2 · C4H4O4
Numero CAS:
Peso molecolare:
386.40
Numero MDL:
Codice UNSPSC:
12352200
ID PubChem:
NACRES:
NA.77

Saggio

≥98% (HPLC)

Forma fisica

powder

Colore

white to beige

Solubilità

DMSO: 32 mg/mL
H2O: insoluble

Stringa SMILE

OC(=O)\C=C/C(O)=O.O=C(C1CC1)c2ccc(OCCCc3c[nH]cn3)cc2

InChI

1S/C16H18N2O2.C4H4O4/c19-16(12-3-4-12)13-5-7-15(8-6-13)20-9-1-2-14-10-17-11-18-14;5-3(6)1-2-4(7)8/h5-8,10-12H,1-4,9H2,(H,17,18);1-2H,(H,5,6)(H,7,8)/b;2-1-
RLQFKEYRALXXEJ-BTJKTKAUSA-N

Applicazioni

Ciproxifan maleate has been used as a selective H3R antagonist to investigate the antidepressant potential of ciproxifan in chronic unpredictable stress (CUS) model of depression in mice. It has also been used as an H3R antagonist to develop in vivo receptor occupancy assay for histamine H3 receptors (H3R)/to determine the occupancy of exogenous H3R antagonists using non-radiolabeled GSK189254 as a tracer in the rat.

Azioni biochim/fisiol

Cyclopropyl 4-(3-(1H-imidazol-4-yl)propyloxy)phenyl methanone (Ciproxifan) is a species-specific histamine H3 receptor (H3R) inverse agonist. It is mainly used as a reference H3R antagonist in rodent models for neurological diseases, Alzheimer′s disease, attention deficit hyperactivity disorder (ADHD), and sleep-wake disorders. It can block monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) enzyme isoforms reversibly in humans and rats.
Potent, selective H3 histamine receptor antagonist.

Caratteristiche e vantaggi

This compound is featured on the Histamine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pittogrammi

Exclamation mark

Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


Certificati d'analisi (COA)

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X Ligneau et al.
The Journal of pharmacology and experimental therapeutics, 287(2), 658-666 (1998-11-10)
Ciproxifan, i.e., cyclopropyl-(4-(3-1H-imidazol-4-yl)propyloxy) phenyl) ketone, belongs to a novel chemical series of histamine H3-receptor antagonists. In vitro, it behaved as a competitive antagonist at the H3 autoreceptor controlling [3H]histamine release from synaptosomes and displayed similar Ki values (0.5-1.9 nM) at
S Hagenow et al.
Scientific reports, 7, 40541-40541 (2017-01-14)
Ciproxifan is a well-investigated histamine H3 receptor (H3R) inverse agonist/antagonist, showing an exclusively high species-specific affinity at rodent compared to human H3R. It is well studied as reference compound for H3R in rodent models for neurological diseases connected with neurotransmitter
Ramakrishna Nirogi et al.
Journal of pharmacological and toxicological methods, 65(3), 115-121 (2012-04-11)
Rapid and reliable preclinical receptor occupancy measurement at the target organ in relevant species is critical in accelerating the drug hunting process. The aim of this study was to develop in vivo receptor occupancy assay for histamine H₃ receptors (H₃R)
Ajeet Kumar et al.
Psychoneuroendocrinology, 101, 128-137 (2018-11-21)
The last two decades of research has established histamine (HA) as a neurotransmitter. Since H3R antagonists are known to modulate several neurotransmitters besides HA, H3R antagonists have shown potential for the treatment of different central nervous system disorders, including depression.

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