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164391-47-3

164391-47-3 Structure

164391-47-3 Structure
IdentificationBack Directory
[Name]

4-(1H-IMIDAZOL-4-YLMETHYL)PIPERIDINE DIHYDROBROMIDE
[CAS]

164391-47-3
[Synonyms]

Zinc00005777
Immepip hydrobromide
IMMEPIP DIHYDROBROMIDE
4-(1H-Imidazol-5-ylmethyl)piperidine hydrobromide
4-(1H-IMIDAZOL-4-YLMETHYL)PIPERIDINE DIHYDROBROMIDE
Piperidine,4-(1H-imidazol-4-ylmethyl)-,dihydrobromide
[Molecular Formula]

C9H17Br2N3
[MDL Number]

MFCD06407876
[MOL File]

164391-47-3.mol
[Molecular Weight]

327.06
Chemical PropertiesBack Directory
[Appearance]

Crystalline Solid
[Melting point ]

234-235℃
[storage temp. ]

2-8°C
[solubility ]

H2O: 7 mg/mL at <40 °C
[form ]

solid
[color ]

light tan
[Water Solubility ]

Soluble to 100 mM in water
[InChI]

1S/C9H15N3.2BrH/c1-2-8(5-10-3-1)4-9-6-11-7-12-9;;/h6-8,10H,1-5H2,(H,11,12);2*1H
[InChIKey]

FXFINNKFZKZVLS-UHFFFAOYSA-N
[SMILES]

Br.Br.C1CNCC(C1)Cc2c[nH]cn2
Hazard InformationBack Directory
[Chemical Properties]

Crystalline Solid
[Uses]

A selective nonchiral histamine H3 agonist
[Biological Activity]

Potent histamine H 3 receptor agonist. Also binds to H 4 receptors (K i values are 0.4 and 9 nM at human recombinant H 3 and H 4 receptors respectively). Equipotent to or slightly more active than (R)- α -methylhistamine at H 3 receptors.
[Description]

Immepip is a histamine H3 receptor agonist (KI = 0.4 nM in SK-N-MC cell membranes expressing the human receptor). It is selective for histamine H3 over H1 and H2 receptors in CHO cell membranes expressing the guinea pig and human receptors, respectively (Kis = >16 μM for both) but also agonizes H4 receptors (KI = 9 nM in SK-N-MC cell membranes expressing the human receptor). Immepip (5 mg/kg, s.c.) decreases hypothalamic histamine release in anesthetized rats. It decreases flinching in the formalin test in rats when administered at doses of 5 and 30 mg/kg and inhibits formalin-induced paw edema at 30 mg/kg.
[storage]

Desiccate at RT
[References]

[1] CHANGLU LIU. Cloning and pharmacological characterization of a fourth histamine receptor (H(4)) expressed in bone marrow.[J]. Molecular Pharmacology, 2001, 59 3 1: 420-426. DOI: 10.1124/mol.59.3.420
[2] ROELAND C. VOLLINGA. A New Potent and Selective Histamine H3 Receptor Agonist, 4-(1H-imidazol-4-ylmethyl)piperidine[J]. Journal of Medicinal Chemistry, 1994, 37 3: 332-333. DOI: 10.1021/jm00029a002
[3] FRANK P JANSEN . In vivo modulation of rat hypothalamic histamine release by the histamine H3 receptor ligands, immepip and clobenpropit. Effects of intrahypothalamic and peripheral application[J]. European journal of pharmacology, 1998, 362 2: Pages 149-155. DOI: 10.1016/s0014-2999(98)00739-0
[4] KERI E. CANNON  Lindsay B H  Rob Leurs. Activation of peripheral and spinal histamine H3 receptors inhibits formalin-induced inflammation and nociception, respectively[J]. Pharmacology Biochemistry and Behavior, 2007, 88 1: Pages 122-129. DOI: 10.1016/j.pbb.2007.07.014
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

22
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
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