Page last updated: 2024-12-07

2-methylhistamine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2-Methylhistamine is a histamine analog that has been shown to possess anti-inflammatory and anti-allergic properties. It is synthesized by the methylation of histamine at the N-2 position. 2-Methylhistamine is a potent agonist of the H2 receptor, which is a G protein-coupled receptor involved in the regulation of gastric acid secretion, smooth muscle contraction, and inflammation. Studies have shown that 2-Methylhistamine can inhibit the release of histamine from mast cells, a key mediator of allergic reactions. This makes it a potential therapeutic target for treating allergic disorders such as asthma and rhinitis. Moreover, 2-Methylhistamine has been investigated for its potential in treating inflammatory bowel disease and other conditions. 2-Methylhistamine is a valuable tool for studying the role of histamine in various physiological processes. Its ability to selectively activate the H2 receptor allows researchers to investigate the downstream signaling pathways and therapeutic implications of this receptor. Research into 2-Methylhistamine continues to explore its potential applications in treating a wide range of inflammatory and allergic diseases.'

2-methylhistamine: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-methylhistamine : An aralkylamino compound that is histamine bearing a methyl substituent at the 2 position on the ring. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID91613
CHEMBL ID12620
CHEBI ID74761
SCHEMBL ID624809
SCHEMBL ID8611446
MeSH IDM0086464

Synonyms (30)

Synonym
1h-imidazole-4-ethanamine, 2-methyl-
bdbm22862
2-methylhistamine
2-(2-methyl-1h-imidazol-4-yl)ethan-1-amine
L000064
CHEMBL12620
chebi:74761 ,
C17928
34392-54-6
2-(2-methyl-1h-imidazol-5-yl)ethanamine
A822902
AKOS012035902
h5dhg2wbhm ,
unii-h5dhg2wbhm
1h-imidazole-5-ethanamine, 2-methyl-
4-(2-aminoethyl)-2-methylimidazole
imidazole, 4-(2-aminoethyl)-2-methyl-
BRD-K96043519-001-01-2
SCHEMBL624809
AB76713
SCHEMBL8611446
2-(2-methyl-1h-imidazol-4-yl)ethylamine #
XDKYTXBAVJELDQ-UHFFFAOYSA-N
2-(2-methyl-1h-imidazol-4-yl)ethanamine
DTXSID00187966
o-methylhistamine
EN300-170661
2-(2-methyl-1h-imidazol-5-yl)ethan-1-amine
CS-0282346
PD180573

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" H1-agonists (2-methylHi and 2-thiazolylethylamine) also depressed the avoidance response; their dose-response lines run parallel to that of Hi."( The effects of histamine and some related compounds on conditioned avoidance response in rats.
Akahori, H; Kamei, C; Kitazumi, K; Tasaka, K, 1985
)
0.27
" If the mice were dosed daily (i."( Effect of histamine agonists and antagonists on the production of murine reaginic antibodies.
Baker, AP; Chakrin, LW; Holden, DA; Smith, WJ; Sung, CP, 1981
)
0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
histamine agonistA drug that binds to and activates histamine receptors. Although they have been suggested for a variety of clinical applications, histamine agonists have so far been more widely used in research than therapeutically.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
aralkylamino compoundAn organic amino compound in which an aminoalkyl group is linked to an arene.
imidazolesA five-membered organic heterocycle containing two nitrogen atoms at positions 1 and 3, or any of its derivatives; compounds containing an imidazole skeleton.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histamine H4 receptorHomo sapiens (human)Ki0.79420.00060.478710.0000AID1798265; AID548981
[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 H1 receptorHomo sapiens (human)EC50 (µMol)0.79430.00040.18810.7943AID548979
Histamine H4 receptorHomo sapiens (human)EC50 (µMol)3.98110.00740.601610.0000AID548982
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID548983Agonist activity at human recombinant histamine H4 receptor expressed in Sf9 cells coexpressing RGS19, Galphai2, Gbeta1gamma2 by steady-state GTPase activity assay relative to histamine2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID87852Evaluated for activity at Histamine H2 receptor in guinea pig ileum1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Histamine H3 ligands: just pharmacological tools or potential therapeutic agents?
AID548982Agonist activity at human recombinant histamine H4 receptor expressed in Sf9 cells coexpressing RGS19, Galphai2, Gbeta1gamma2 by steady-state GTPase activity assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID194444Relative inhibition of [3H]histamine release from pre-loaded slices of rat cerebral cortex1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Histamine H3 ligands: just pharmacological tools or potential therapeutic agents?
AID548980Agonist activity at human recombinant histamine H1 receptor expressed in Sf9 cells coexpressing RGS4 by steady-state GTPase activity assay relative to histamine2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID86257Evaluated for activity at Histamine H1 receptor in guinea pig ileum1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Histamine H3 ligands: just pharmacological tools or potential therapeutic agents?
AID157860In vitro antimalarial activity against chloroquine-sensitive Plasmodium falciparum2002Bioorganic & medicinal chemistry letters, Jul-08, Volume: 12, Issue:13
Antimalarial activities of ring-substituted bioimidazoles.
AID548979Agonist activity at human recombinant histamine H1 receptor expressed in Sf9 cells coexpressing RGS4 by steady-state GTPase activity assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID86750Contractile effect on isolated guinea pig ileal segments is a measure of H1 (histamine) receptor agonistic activity relative to histamine.1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (52)

TimeframeStudies, This Drug (%)All Drugs %
pre-199028 (53.85)18.7374
1990's18 (34.62)18.2507
2000's3 (5.77)29.6817
2010's1 (1.92)24.3611
2020's2 (3.85)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.47

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 Index10.47 (24.57)
Research Supply Index3.99 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.47)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.92%)5.53%
Reviews2 (3.85%)6.00%
Case Studies1 (1.92%)4.05%
Observational0 (0.00%)0.25%
Other48 (92.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]