Synonym
Immepip (hydrobromide)
IUPAC/Chemical Name
4-(1H-imidazol-5-ylmethyl)-piperidine, dihydrobromide
InChi Key
YGNJPNRDGXJQJX-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H15N3.2BrH/c1-3-10-4-2-8(1)5-9-6-11-7-12-9;;/h6-8,10H,1-5H2,(H,11,12);2*1H
SMILES Code
[H]Br.[H]Br.C1(CC2=CN=CN2)CCNCC1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Immepip (hydrobromide) is a histamine H3 receptor agonist selective for histamine H3 over H1 and H2 receptors in CHO cell membranes expressing the guinea pig and human receptors.
In vitro activity:
Serum glucagon concentration after a 24-h fast was remarkably inhibited by 1 μM immepip (75.3 ± 14.5 pg/mL versus 130.0 ± 12.8 pg/mL, P < 0.05; Fig. 4), indicating that H3R was involved in the regulation of serum glucagon concentration in rats in vivo.
Reference: FEBS Open Bio. 2014 Dec 13;5:36-41. https://pubmed.ncbi.nlm.nih.gov/25685663/
In vivo activity:
H3R antagonist ciproxifan suppressed and H3R agonist immepip increased alcohol drinking in C57BL/6J mice. Impairment in reward mechanisms in H3R KO mice was confirmed by the lack of alcohol-evoked conditioned place preference.
Reference: Neuropsychopharmacology. 2011 Sep;36(10):2030-40. https://pubmed.ncbi.nlm.nih.gov/21654737/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Water |
32.7 |
100.01 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
327.06
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Annamalai B, Ragu Varman D, Horton RE, Daws LC, Jayanthi LD, Ramamoorthy S. Histamine Receptors Regulate the Activity, Surface Expression, and Phosphorylation of Serotonin Transporters. ACS Chem Neurosci. 2020 Feb 5;11(3):466-476. doi: 10.1021/acschemneuro.9b00664. Epub 2020 Jan 22. PMID: 31916747; PMCID: PMC7004881.
2. Nakamura T, Yoshikawa T, Naganuma F, Mohsen A, Iida T, Miura Y, Sugawara A, Yanai K. Role of histamine H3 receptor in glucagon-secreting αTC1.6 cells. FEBS Open Bio. 2014 Dec 13;5:36-41. doi: 10.1016/j.fob.2014.12.001. PMID: 25685663; PMCID: PMC4309840.
3. Nuutinen S, Lintunen M, Vanhanen J, Ojala T, Rozov S, Panula P. Evidence for the role of histamine H3 receptor in alcohol consumption and alcohol reward in mice. Neuropsychopharmacology. 2011 Sep;36(10):2030-40. doi: 10.1038/npp.2011.90. Epub 2011 Jun 8. PMID: 21654737; PMCID: PMC3158320.
4. Cannon KE, Leurs R, Hough LB. Activation of peripheral and spinal histamine H3 receptors inhibits formalin-induced inflammation and nociception, respectively. Pharmacol Biochem Behav. 2007 Nov;88(1):122-9. doi: 10.1016/j.pbb.2007.07.014. Epub 2007 Jul 25. PMID: 17719621; PMCID: PMC2064035.
In vitro protocol:
1. Annamalai B, Ragu Varman D, Horton RE, Daws LC, Jayanthi LD, Ramamoorthy S. Histamine Receptors Regulate the Activity, Surface Expression, and Phosphorylation of Serotonin Transporters. ACS Chem Neurosci. 2020 Feb 5;11(3):466-476. doi: 10.1021/acschemneuro.9b00664. Epub 2020 Jan 22. PMID: 31916747; PMCID: PMC7004881.
2. Nakamura T, Yoshikawa T, Naganuma F, Mohsen A, Iida T, Miura Y, Sugawara A, Yanai K. Role of histamine H3 receptor in glucagon-secreting αTC1.6 cells. FEBS Open Bio. 2014 Dec 13;5:36-41. doi: 10.1016/j.fob.2014.12.001. PMID: 25685663; PMCID: PMC4309840.
In vivo protocol:
1. Nuutinen S, Lintunen M, Vanhanen J, Ojala T, Rozov S, Panula P. Evidence for the role of histamine H3 receptor in alcohol consumption and alcohol reward in mice. Neuropsychopharmacology. 2011 Sep;36(10):2030-40. doi: 10.1038/npp.2011.90. Epub 2011 Jun 8. PMID: 21654737; PMCID: PMC3158320.
2. Cannon KE, Leurs R, Hough LB. Activation of peripheral and spinal histamine H3 receptors inhibits formalin-induced inflammation and nociception, respectively. Pharmacol Biochem Behav. 2007 Nov;88(1):122-9. doi: 10.1016/j.pbb.2007.07.014. Epub 2007 Jul 25. PMID: 17719621; PMCID: PMC2064035.
1. Liu, C., Ma, X., Jiang, X., et al. Cloning and pharmacological characterization of a fourth histamine receptor (H4) expressed in bone marrow. Mol. Pharmacol. 59(3), 420-426 (2001).
2. Vollinga, R.C., de Koning, J.P., Jansen, F.P., et al. A new potent and selective histamine H3 receptor agonist, 4-(1H-imidazol-4-ylmethyl)piperidine. J. Med. Chem. 37(3), 332-333 (1994).
3. Jansen, F.P., Mochizuki, T., Yamamoto, Y., et al. In vivo modulation of rat hypothalamic histamine release by the histamine H3 receptor ligands, immepip and clobenpropit. Effects of intrahypothalamic and peripheral application. Eur. J. Pharmacol. 362(2-3), 149-155 (1998).
4. Cannon, K.E., Leurs, R., and Hough, L.B. Activation of peripheral and spinal histamine H3 receptors inhibits formalin-induced inflammation and nociception, respectively. Pharmacol. Biochem. Behav. 88(1), 122-129 (2007).
