Page last updated: 2024-10-14

methimepip

Description

methimepip: histamine H3 agonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11313837
CHEMBL ID175782
SCHEMBL ID8320104
MeSH IDM000604356

Synonyms (18)

Synonym
4-(3h-imidazol-4-ylmethyl)-1-methylpiperidine
gtpl1254
bdbm22909
methimepip
4-(1h-imidazol-5-ylmethyl)-1-methylpiperidine
L009044
CHEMBL175782
151070-80-3
SCHEMBL8320104
bdbm50475340
Q6593527
4-((1h-imidazol-5-yl)methyl)-1-methylpiperidine
piperidine, 4-(1h-imidazol-5-ylmethyl)-1-methyl-
unii-259ysh2wl6
piperidine, 4-(1h-imidazol-4-ylmethyl)-1-methyl-
259ysh2wl6 ,
4-(1h-imidazol-4-ylmethyl)-1-methylpiperidine
DTXSID501027200
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histamine H2 receptorHomo sapiens (human)Ki10.00000.00062.197310.0000AID239970
Histamine H1 receptorHomo sapiens (human)Ki10.00000.00000.511010.0000AID239969
Histamine H4 receptorHomo sapiens (human)Ki1.99520.00060.478710.0000AID1798265; AID239948; AID548981
Histamine H3 receptorHomo sapiens (human)Ki0.00100.00010.33998.5110AID1798266; AID239947; AID408541; AID548987
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histamine H4 receptorHomo sapiens (human)EC50 (µMol)5.01190.00740.601610.0000AID548993
Histamine H3 receptorHomo sapiens (human)EC50 (µMol)0.00030.00000.09473.1623AID249512; AID408552; AID548991
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
gastric acid secretionHistamine H2 receptorHomo sapiens (human)
immune responseHistamine H2 receptorHomo sapiens (human)
positive regulation of vasoconstrictionHistamine H2 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H2 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H2 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H2 receptorHomo sapiens (human)
inflammatory responseHistamine H1 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
memoryHistamine H1 receptorHomo sapiens (human)
visual learningHistamine H1 receptorHomo sapiens (human)
regulation of vascular permeabilityHistamine H1 receptorHomo sapiens (human)
positive regulation of vasoconstrictionHistamine H1 receptorHomo sapiens (human)
regulation of synaptic plasticityHistamine H1 receptorHomo sapiens (human)
cellular response to histamineHistamine H1 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H1 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H1 receptorHomo sapiens (human)
inflammatory responseHistamine H4 receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationHistamine H4 receptorHomo sapiens (human)
biological_processHistamine H4 receptorHomo sapiens (human)
regulation of MAPK cascadeHistamine H4 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H4 receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayHistamine H4 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H4 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H4 receptorHomo sapiens (human)
neurotransmitter secretionHistamine H3 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H3 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H3 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H3 receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayHistamine H3 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
histamine receptor activityHistamine H2 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H2 receptorHomo sapiens (human)
neurotransmitter receptor activityHistamine H2 receptorHomo sapiens (human)
histamine receptor activityHistamine H1 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H1 receptorHomo sapiens (human)
neurotransmitter receptor activityHistamine H1 receptorHomo sapiens (human)
histamine receptor activityHistamine H4 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H4 receptorHomo sapiens (human)
G protein-coupled acetylcholine receptor activityHistamine H4 receptorHomo sapiens (human)
histamine receptor activityHistamine H3 receptorHomo sapiens (human)
G protein-coupled acetylcholine receptor activityHistamine H3 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H3 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membraneHistamine H2 receptorHomo sapiens (human)
synapseHistamine H2 receptorHomo sapiens (human)
plasma membraneHistamine H2 receptorHomo sapiens (human)
dendriteHistamine H2 receptorHomo sapiens (human)
cytosolHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H1 receptorHomo sapiens (human)
synapseHistamine H1 receptorHomo sapiens (human)
dendriteHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H4 receptorHomo sapiens (human)
plasma membraneHistamine H4 receptorHomo sapiens (human)
dendriteHistamine H4 receptorHomo sapiens (human)
synapseHistamine H4 receptorHomo sapiens (human)
plasma membraneHistamine H3 receptorHomo sapiens (human)
presynapseHistamine H3 receptorHomo sapiens (human)
plasma membraneHistamine H3 receptorHomo sapiens (human)
synapseHistamine H3 receptorHomo sapiens (human)
dendriteHistamine H3 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID548993Agonist activity at human histamine H4 receptor expressed in human SK-N-MC cells by CRE-beta galactosidase reporter gene assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID252999Intrinsic activity as relative maximum response at histamine H3 receptor expressed in SK-N-MC cells2005Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6
N-substituted piperidinyl alkyl imidazoles: discovery of methimepip as a potent and selective histamine H3 receptor agonist.
AID548981Displacement of [3H]-histamine from human histamine H4 receptor expressed in Sf9 cells coexpressing RGS19, Galphai2, Gbeta1gamma22010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID548994Agonist activity at human histamine H4 receptor expressed in human SK-N-MC cells by CRE-beta galactosidase reporter gene assay relative to histamine2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID239969Displacement of [3H]mepyramine binding to COS-7 cell membranes expressing human histamine H1 receptor2005Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6
N-substituted piperidinyl alkyl imidazoles: discovery of methimepip as a potent and selective histamine H3 receptor agonist.
AID245847Effect on guinea pig ileal muscle contraction evoked by electrical field stimulation (EFS)2005Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6
N-substituted piperidinyl alkyl imidazoles: discovery of methimepip as a potent and selective histamine H3 receptor agonist.
AID239970Displacement of [125I]aminopotentidine binding to CHO cell membranes expressing human histamine H2 receptor2005Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6
N-substituted piperidinyl alkyl imidazoles: discovery of methimepip as a potent and selective histamine H3 receptor agonist.
AID548992Agonist activity at human histamine H3 receptor expressed in human SK-N-MC cells by CRE-beta galactosidase reporter gene assay relative to histamine2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID249512Inhibition of cAMP-stimulated beta-galactosidase transcription in SK-N-MC cells expressing human H3 receptor2005Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6
N-substituted piperidinyl alkyl imidazoles: discovery of methimepip as a potent and selective histamine H3 receptor agonist.
AID239947Displacement of [3H]N-R-methylhistamine binding to SK-N-MC cell membranes expressing human H3 receptor2005Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6
N-substituted piperidinyl alkyl imidazoles: discovery of methimepip as a potent and selective histamine H3 receptor agonist.
AID548987Displacement of [3H]Nalpha-methylhistamine from human histamine H3 receptor expressed in human SK-N-MC cells2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID548991Agonist activity at human histamine H3 receptor expressed in human SK-N-MC cells by CRE-beta galactosidase reporter gene assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID408541Displacement of [3H]N-alpha-methylhistamine from human histamine H3 receptor expressed in CHO cells2008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
4-benzyl-1H-imidazoles with oxazoline termini as histamine H3 receptor agonists.
AID239948Displacement of [3H]histamine binding to SK-N-MC cell membranes expressing human histamine H4 receptor2005Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6
N-substituted piperidinyl alkyl imidazoles: discovery of methimepip as a potent and selective histamine H3 receptor agonist.
AID549000Selectivity ratio of EC50 for human histamine H3 receptor to EC50 for human histamine H4 receptor2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID408552Agonist activity at human histamine H3 receptor assessed as beta galactosidase activity2008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
4-benzyl-1H-imidazoles with oxazoline termini as histamine H3 receptor agonists.
AID1798266H3R Radioligand Binding Assay from Article 10.1124/jpet.105.087965: \\Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist.\\2005The Journal of pharmacology and experimental therapeutics, Sep, Volume: 314, Issue:3
Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist.
AID1798265H4R Radioligand Binding Assay from Article 10.1124/jpet.105.087965: \\Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist.\\2005The Journal of pharmacology and experimental therapeutics, Sep, Volume: 314, Issue:3
Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist.
AID1346107Human H3 receptor (Histamine receptors)2005Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6
N-substituted piperidinyl alkyl imidazoles: discovery of methimepip as a potent and selective histamine H3 receptor agonist.
AID1346055Human H4 receptor (Histamine receptors)2005Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6
N-substituted piperidinyl alkyl imidazoles: discovery of methimepip as a potent and selective histamine H3 receptor agonist.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (50.00)29.6817
2010's3 (50.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]