Page last updated: 2024-11-12

4-(1h-imidazol-4-yl)butanamine

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Description

4-(1H-imidazol-4-yl)butanamine: agonist of both H3 and H4 histamine receptors; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID13499360
CHEMBL ID90019
SCHEMBL ID3885328
MeSH IDM000595584

Synonyms (16)

Synonym
CHEMBL90019
4-(3h-imidazol-4-yl)butan-1-amine
gtpl1249
bdbm22907
4-(1h-imidazol-5-yl)butan-1-amine
imbutamine
AKOS006310860
SCHEMBL3885328
4-(1h-imidazol-4-yl)butanamine
imidazole-4-butanamine
VJSUMPPMFYQOMP-UHFFFAOYSA-N
4-(4-aminobutyl)imidazole
40546-47-2
DTXSID90542303
bdbm50170164
EN300-1816934
[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)Ki794.32800.00062.197310.0000AID88467
Histamine H1 receptorCavia porcellus (domestic guinea pig)Ki398.10700.00261.783210.0000AID87063
Histamine H4 receptorHomo sapiens (human)Ki11,530,516,387,157.34200.00060.478710.0000AID1300612; AID1798265; AID262566; AID548981; AID90038; AID90039
Histamine H3 receptorHomo sapiens (human)Ki0.00410.00010.33998.5110AID1300611; AID1798266; AID262564; AID548987; AID86615; AID86619
[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)0.07000.00740.601610.0000AID548993; AID90032; AID90035
Histamine H3 receptorHomo sapiens (human)EC50 (µMol)0.00510.00000.09473.1623AID262565; AID548991; AID86476; AID86478
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

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 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 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 (4)

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)
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 (30)

Assay IDTitleYearJournalArticle
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.
AID1300611Displacement of [3H]N-alpha-methylhistamine from human histamine H3 receptor expressed in human SK-N-MC cells incubated for 40 mins2016Journal of medicinal chemistry, Apr-14, Volume: 59, Issue:7
Conformational Restriction and Enantioseparation Increase Potency and Selectivity of Cyanoguanidine-Type Histamine H4 Receptor Agonists.
AID262566Displacement of [3H]histamine from human H4 receptor expressed in SK-N-MC cells2006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
A chemical switch for the modulation of the functional activity of higher homologues of histamine on the human histamine H3 receptor: effect of various substitutions at the primary amino function.
AID227604Maximum response compared to histamine against either H3 or H4 receptors2004Journal of medicinal chemistry, May-06, Volume: 47, Issue:10
Identification of 4-(1H-imidazol-4(5)-ylmethyl)pyridine (immethridine) as a novel, potent, and highly selective histamine H(3) receptor agonist.
AID87063Binding affinity for H1 receptor of guinea pig by the displacement of [3H]mepyramine, bound to membranes of CHO cells1995Journal of medicinal chemistry, Jan-20, Volume: 38, Issue:2
Homologs of histamine as histamine H3 receptor antagonists: a new potent and selective H3 antagonist, 4(5)-(5-aminopentyl)-1H-imidazole.
AID89898Intrinsic activity for Histamine H4 receptor2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Synthesis and structure-activity relationships of conformationally constrained histamine H(3) receptor agonists.
AID86620Selectivity is the ratio of inhibitory activity against Histamine H3 receptor to that of Histamine H4 receptor2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Synthesis and structure-activity relationships of conformationally constrained histamine H(3) receptor agonists.
AID262565Activity against human H3 receptor as measured by CRE-mediated beta galactosidase reporter gene assay in forskolin-stimulated SK-N-MC cells2006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
A chemical switch for the modulation of the functional activity of higher homologues of histamine on the human histamine H3 receptor: effect of various substitutions at the primary amino function.
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.
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.
AID86619Inhibitory activity measured by [3H]- N alpha- methyl-histamine binding to membranes of SK-N-MC cells expressing the human Histamine H3 receptor2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Synthesis and structure-activity relationships of conformationally constrained histamine H(3) receptor agonists.
AID1300612Displacement of [3H]histamine from human histamine H4 receptor expressed in human SK-N-MC cell membrane incubated for 60 mins2016Journal of medicinal chemistry, Apr-14, Volume: 59, Issue:7
Conformational Restriction and Enantioseparation Increase Potency and Selectivity of Cyanoguanidine-Type Histamine H4 Receptor Agonists.
AID86615Displacement of [3H]N-alpha-methylhistamine from human histamine H3 receptor expressed in SK-N-MC cells2004Journal of medicinal chemistry, May-06, Volume: 47, Issue:10
Identification of 4-(1H-imidazol-4(5)-ylmethyl)pyridine (immethridine) as a novel, potent, and highly selective histamine H(3) receptor agonist.
AID86476Inhibition of the cAMP-stimulated beta-galactosidase transcription in SK-N-MC cells expressing the human Histamine H3 receptor2004Journal of medicinal chemistry, May-06, Volume: 47, Issue:10
Identification of 4-(1H-imidazol-4(5)-ylmethyl)pyridine (immethridine) as a novel, potent, and highly selective histamine H(3) receptor agonist.
AID86455Intrinsic activity determined towards Histamine H3 receptor2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Synthesis and structure-activity relationships of conformationally constrained histamine H(3) receptor agonists.
AID90038Displacement of [3H]histamine from human histamine H4 receptor expressed in SK-N-MC cells2004Journal of medicinal chemistry, May-06, Volume: 47, Issue:10
Identification of 4-(1H-imidazol-4(5)-ylmethyl)pyridine (immethridine) as a novel, potent, and highly selective histamine H(3) receptor agonist.
AID89906Selectivity expressed as the ratio of Ki for Histamine H4 receptor to that of Ki for Histamine H3 receptor2004Journal of medicinal chemistry, May-06, Volume: 47, Issue:10
Identification of 4-(1H-imidazol-4(5)-ylmethyl)pyridine (immethridine) as a novel, potent, and highly selective histamine H(3) receptor agonist.
AID90039Inhibitory activity measured by [3H]- N alpha- methyl-histamine binding to membranes of SK-N-MC cells expressing the human Histamine H4 receptor2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Synthesis and structure-activity relationships of conformationally constrained histamine H(3) receptor agonists.
AID86297Tested in vitro for antagonist activity against H3 receptor of guinea pig jejunum.1995Journal of medicinal chemistry, Jan-20, Volume: 38, Issue:2
Homologs of histamine as histamine H3 receptor antagonists: a new potent and selective H3 antagonist, 4(5)-(5-aminopentyl)-1H-imidazole.
AID88467Binding affinity against human H2 receptor by the displacement of [125I]iodoaminopotentidine bound to membranes of CHO cells.1995Journal of medicinal chemistry, Jan-20, Volume: 38, Issue:2
Homologs of histamine as histamine H3 receptor antagonists: a new potent and selective H3 antagonist, 4(5)-(5-aminopentyl)-1H-imidazole.
AID262564Displacement of [3H]N-alpha-methylhistamine from human H3 receptor expressed in SK-N-MC cells2006Journal of medicinal chemistry, Apr-20, Volume: 49, Issue:8
A chemical switch for the modulation of the functional activity of higher homologues of histamine on the human histamine H3 receptor: effect of various substitutions at the primary amino function.
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.
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.
AID90035Inhibitory activity determined by the inhibition of cAMP- stimulated beta-galactosidase transcription in SK-N-MC cells expressing the human Histamine H4 receptor2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Synthesis and structure-activity relationships of conformationally constrained histamine H(3) receptor agonists.
AID90032Inhibition of the cAMP-stimulated beta-galactosidase transcription in SK-N-MC cells expressing the human Histamine H4 receptor2004Journal of medicinal chemistry, May-06, Volume: 47, Issue:10
Identification of 4-(1H-imidazol-4(5)-ylmethyl)pyridine (immethridine) as a novel, potent, and highly selective histamine H(3) receptor agonist.
AID86478Inhibitory activity determined by the inhibition of cAMP- stimulated beta-galactosidase transcription in SK-N-MC cells expressing the human Histamine H3 receptor2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Synthesis and structure-activity relationships of conformationally constrained histamine H(3) receptor agonists.
AID1346107Human H3 receptor (Histamine receptors)2003Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25
Synthesis and structure-activity relationships of conformationally constrained histamine H(3) receptor agonists.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (12.50)18.2507
2000's4 (50.00)29.6817
2010's3 (37.50)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.73

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.73 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.93 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.73)

All Compounds (24.57)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]