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Chemical Compound Review

Immepip     4-(3H-imidazol-4- ylmethyl)piperidine

Synonyms: Tocris-0932, CHEMBL18661, AG-D-97885, SureCN3338054, SureCN6347746, ...
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Disease relevance of Immepip


Psychiatry related information on Immepip

  • The results showed that the same i.p. doses of 5 and 10 mg kg(-1) of immepip was devoid of any significant impact on the sleep/wake phases (active awake, drowsiness and slow wave sleep), except for a slight, albeit significant, decrease in sleep onset latency [3].

High impact information on Immepip


Biological context of Immepip

  • The accumulation of [3H]cAMP induced by 1 microM SKF-81297 was inhibited in a concentration-dependent manner by the selective H3 receptor agonist immepip (maximal inhibition 60+/-5%, IC50 13 +/- 5 nM) [7].
  • Neither the density of [3H]SCH-23390 binding sites (D1 receptors) nor the inhibition by SKF-81297 were affected by 1 microM immepip, ruling out a direct interaction between D1 and H3 receptors [7].

Anatomical context of Immepip


Associations of Immepip with other chemical compounds

  • In perfused ileal segments, specific agonists acting at histamine H3 receptors, ((R)-alpha-methylhistamine and immepip, 1 nmol-10 micromol/l), did not cause any change in the threshold pressure for triggering the peristaltic wave, or in the rise of the perfusion pressure during the emptying phase [11].
  • Hydroxyzine prevents isolation-induced vocalization in guinea pig pups: comparison with chlorpheniramine and immepip [12].

Analytical, diagnostic and therapeutic context of Immepip

  • Using the microdialysis technique in freely moving rats, we found that the histaminergic H3 agonists R-alpha-methylhistamine (RAMH) and immepip, directly administered into the BLA, augmented spontaneous release of ACh in a similar manner [13].
  • This study reports the effect of a potent and selective H3 agonist, immepip, on EEG assessed sleep/wake phases in Sprague-Dawley rats at doses that significantly modulate brain histamine release [3].


  1. Pre-synaptic histamine H(3) receptors regulate glutamate, but not GABA release in rat thalamus. Garduño-Torres, B., Treviño, M., Gutiérrez, R., Arias-Montaño, J.A. Neuropharmacology (2007) [Pubmed]
  2. Histamine H3 receptor agonists reduce L-dopa-induced chorea, but not dystonia, in the MPTP-lesioned nonhuman primate model of Parkinson's disease. Gomez-Ramirez, J., Johnston, T.H., Visanji, N.P., Fox, S.H., Brotchie, J.M. Mov. Disord. (2006) [Pubmed]
  3. H3 agonist immepip markedly reduces cortical histamine release, but only weakly promotes sleep in the rat. Lamberty, Y., Margineanu, D.G., Dassesse, D., Klitgaard, H. Pharmacol. Res. (2003) [Pubmed]
  4. A new potent and selective histamine H3 receptor agonist, 4-(1H-imidazol-4-ylmethyl)piperidine. Vollinga, R.C., de Koning, J.P., Jansen, F.P., Leurs, R., Menge, W.M., Timmerman, H. J. Med. Chem. (1994) [Pubmed]
  5. Identification of zebrafish histamine H(1), H(2) and H(3) receptors and effects of histaminergic ligands on behavior. Peitsaro, N., Sundvik, M., Anichtchik, O.V., Kaslin, J., Panula, P. Biochem. Pharmacol. (2007) [Pubmed]
  6. Histamine H3 receptor activation selectively inhibits dopamine D1 receptor-dependent [3H]GABA release from depolarization-stimulated slices of rat substantia nigra pars reticulata. Garcia, M., Floran, B., Arias-Montaño, J.A., Young, J.M., Aceves, J. Neuroscience (1997) [Pubmed]
  7. Histamine H3 receptor activation inhibits dopamine D1 receptor-induced cAMP accumulation in rat striatal slices. Sánchez-Lemus, E., Arias-Montaño, J.A. Neurosci. Lett. (2004) [Pubmed]
  8. Pharmacological analysis of immepip and imetit homologues. Further evidence for histamine H(3) receptor heterogeneity? Alves-Rodrigues, A., Lemstra, S., Vollinga, R.C., Menge, W.M., Timmerman, H., Leurs, R. Behav. Brain Res. (2001) [Pubmed]
  9. Activation of spinal histamine H3 receptors inhibits mechanical nociception. Cannon, K.E., Nalwalk, J.W., Stadel, R., Ge, P., Lawson, D., Silos-Santiago, I., Hough, L.B. Eur. J. Pharmacol. (2003) [Pubmed]
  10. In vivo modulation of rat hypothalamic histamine release by the histamine H3 receptor ligands, immepip and clobenpropit. Effects of intrahypothalamic and peripheral application. Jansen, F.P., Mochizuki, T., Yamamoto, Y., Timmerman, H., Yamatodani, A. Eur. J. Pharmacol. (1998) [Pubmed]
  11. Histamine H3 receptors do not modulate reflex-evoked peristaltic motility in the isolated guinea-pig ileum. Poli, E., Pozzoli, C. Eur. J. Pharmacol. (1997) [Pubmed]
  12. Hydroxyzine prevents isolation-induced vocalization in guinea pig pups: comparison with chlorpheniramine and immepip. Lamberty, Y., Gower, A.J. Pharmacol. Biochem. Behav. (2004) [Pubmed]
  13. Activation of histaminergic H3 receptors in the rat basolateral amygdala improves expression of fear memory and enhances acetylcholine release. Cangioli, I., Baldi, E., Mannaioni, P.F., Bucherelli, C., Blandina, P., Passani, M.B. Eur. J. Neurosci. (2002) [Pubmed]
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