Related CAS #
151070-80-3 (HBr); 151070-79-0 (HCl)
Synonym
Methimepip dihydrobromide; Methimepip HBr
IUPAC/Chemical Name
4-((1H-imidazol-4-yl)methyl)-1-methylpiperidine dihydrobromide
InChi Key
XTJPHXJFOFOXJG-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H17N3.2BrH/c1-13-4-2-9(3-5-13)6-10-7-11-8-12-10;;/h7-9H,2-6H2,1H3,(H,11,12);2*1H
SMILES Code
CN(CC1)CCC1CC2=CNC=N2.[H]Br.[H]Br
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:
Methimepip dihydrobromide is a histamine agonist which is highly selective for the H3 subtype.
In vitro activity:
This study observed that N-methyl-substituted immepip (methimepip) exhibits high affinity and agonist activity at the human histamine H(3) receptor (pK(i) = 9.0 and pEC(50) = 9.5) with a 2000-fold selectivity at the human H(3) receptor over the human H(4) receptor and more than a 10000-fold selectivity over the human histamine H(1) and H(2) receptors.
Reference: J Med Chem. 2005 Mar 24;48(6):2100-7. https://pubmed.ncbi.nlm.nih.gov/15771452/
In vivo activity:
To further investigate this mechanism, this study examined the effect of methimepip, a selective histamine H3 receptor agonist, on DG (dentate gyrus) granule cell responses and LTP (long-term potentiation) in saccharin control and PAE (prenatal alcohol-exposed) rats. In control offspring, methimepip reduced the coupling of fast excitatory postsynaptic field potentials to population spikes (E-S coupling), the probability of glutamate release, as measured by paired-pulse ratio (PPR) and diminished DG LTP.
Reference: Alcohol Clin Exp Res. 2014 Jul;38(7):1902-11. https://pubmed.ncbi.nlm.nih.gov/24818819/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
341.09
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. Dandekar RD, Khan MM. Regulation of ERK2 phosphorylation by histamine in splenocytes. Immunopharmacol Immunotoxicol. 2011 Jun;33(2):250-8. doi: 10.3109/08923973.2010.499913. PMID: 21554104.
2. Kitbunnadaj R, Hashimoto T, Poli E, Zuiderveld OP, Menozzi A, Hidaka R, de Esch IJ, Bakker RA, Menge WM, Yamatodani A, Coruzzi G, Timmerman H, Leurs R. N-substituted piperidinyl alkyl imidazoles: discovery of methimepip as a potent and selective histamine H3 receptor agonist. J Med Chem. 2005 Mar 24;48(6):2100-7. doi: 10.1021/jm049475h. PMID: 15771452.
3. Varaschin RK, Rosenberg MJ, Hamilton DA, Savage DD. Differential effects of the histamine H(3) receptor agonist methimepip on dentate granule cell excitability, paired-pulse plasticity and long-term potentiation in prenatal alcohol-exposed rats. Alcohol Clin Exp Res. 2014 Jul;38(7):1902-11. doi: 10.1111/acer.12430. Epub 2014 May 12. PMID: 24818819; PMCID: PMC5094461.
4. Abuhamdah RM, van Rensburg R, Lethbridge NL, Ennaceur A, Chazot PL. Effects of methimepip and JNJ-5207852 in Wistar rats exposed to an open-field with and without object and in Balb/c mice exposed to a radial-arm maze. Front Syst Neurosci. 2012 Jul 16;6:54. doi: 10.3389/fnsys.2012.00054. PMID: 22811660; PMCID: PMC3397409.
In vitro protocol:
1. Dandekar RD, Khan MM. Regulation of ERK2 phosphorylation by histamine in splenocytes. Immunopharmacol Immunotoxicol. 2011 Jun;33(2):250-8. doi: 10.3109/08923973.2010.499913. PMID: 21554104.
2. Kitbunnadaj R, Hashimoto T, Poli E, Zuiderveld OP, Menozzi A, Hidaka R, de Esch IJ, Bakker RA, Menge WM, Yamatodani A, Coruzzi G, Timmerman H, Leurs R. N-substituted piperidinyl alkyl imidazoles: discovery of methimepip as a potent and selective histamine H3 receptor agonist. J Med Chem. 2005 Mar 24;48(6):2100-7. doi: 10.1021/jm049475h. PMID: 15771452.
In vivo protocol:
1. Varaschin RK, Rosenberg MJ, Hamilton DA, Savage DD. Differential effects of the histamine H(3) receptor agonist methimepip on dentate granule cell excitability, paired-pulse plasticity and long-term potentiation in prenatal alcohol-exposed rats. Alcohol Clin Exp Res. 2014 Jul;38(7):1902-11. doi: 10.1111/acer.12430. Epub 2014 May 12. PMID: 24818819; PMCID: PMC5094461.
2. Abuhamdah RM, van Rensburg R, Lethbridge NL, Ennaceur A, Chazot PL. Effects of methimepip and JNJ-5207852 in Wistar rats exposed to an open-field with and without object and in Balb/c mice exposed to a radial-arm maze. Front Syst Neurosci. 2012 Jul 16;6:54. doi: 10.3389/fnsys.2012.00054. PMID: 22811660; PMCID: PMC3397409.
1: Varaschin RK, Rosenberg MJ, Hamilton DA, Savage DD. Differential effects of the histamine H(3) receptor agonist methimepip on dentate granule cell excitability, paired-pulse plasticity and long-term potentiation in prenatal alcohol-exposed rats. Alcohol Clin Exp Res. 2014 Jul;38(7):1902-11. doi: 10.1111/acer.12430. Epub 2014 May 12. PubMed PMID: 24818819; PubMed Central PMCID: PMC5094461.
2: Abuhamdah RM, van Rensburg R, Lethbridge NL, Ennaceur A, Chazot PL. Effects of methimepip and JNJ-5207852 in Wistar rats exposed to an open-field with and without object and in Balb/c mice exposed to a radial-arm maze. Front Syst Neurosci. 2012 Jul 16;6:54. doi: 10.3389/fnsys.2012.00054. eCollection 2012. PubMed PMID: 22811660; PubMed Central PMCID: PMC3397409.
3: Kitbunnadaj R, Hashimoto T, Poli E, Zuiderveld OP, Menozzi A, Hidaka R, de Esch IJ, Bakker RA, Menge WM, Yamatodani A, Coruzzi G, Timmerman H, Leurs R. N-substituted piperidinyl alkyl imidazoles: discovery of methimepip as a potent and selective histamine H3 receptor agonist. J Med Chem. 2005 Mar 24;48(6):2100-7. PubMed PMID: 15771452.
