4-(1H-IMIDAZOL-4-YLMETHYL)PIPERIDINE DIHYDROBROMIDE Chemical Properties

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

MSDS

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4-(1H-IMIDAZOL-4-YLMETHYL)PIPERIDINE DIHYDROBROMIDE Usage And Synthesis

Description

Immepip is a histamine H₃ receptor agonist (K_I = 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 (K_is = >16 μM for both) but also agonizes H₄ receptors (K_I = 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.

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.

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

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