Page last updated: 2024-11-04

n-methylhistamine

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

N-methylhistamine (N-MH) is a naturally occurring histamine derivative, found in various biological systems. It exhibits a range of pharmacological properties, including potent agonistic activity at the H3 receptor, which is involved in regulating histamine release and neuronal activity. Notably, N-MH has been shown to possess anti-inflammatory and neuroprotective effects in preclinical studies. Its synthesis involves methylation of the amine group of histamine. Researchers are studying N-MH for its potential therapeutic applications, particularly in conditions related to inflammation, neurodegenerative disorders, and allergic responses.'

Cross-References

ID SourceID
PubMed CID912
CHEMBL ID268490
CHEBI ID184982
SCHEMBL ID119179
SCHEMBL ID2086409
MeSH IDM0138667

Synonyms (55)

Synonym
unii-y7qr253130
y7qr253130 ,
n-alpha-meha
gtpl1239
[3h]namh
[3h]-na-methylhistamine
gtpl1240
n-[3h]alpha-methylhistamine
2-(3h-imidazol-4-yl)-n-methylethanamine
1h-imidazole-4-ethanamine, n-methyl-
imidazole, 4-(2-(methylamino)ethyl)-
n(sup alpha)-methylhistamine
4-(2-methylaminoethyl)imidazole
n-alpha-methylhistamine
namh
[2-(1h-imidazol-5-yl)ethyl](methyl)amine
bdbm22530
n(alpha)-methylhistamine
[3h]n-alpha-methyl histamine
tocris-0573
NCGC00024660-01
PDSP1_000543
NCGC00024660-03
PDSP2_000541
NCGC00024660-02
673-50-7
L000451
CHEMBL268490
nalpha-methylhistamine
AKOS006348059
CHEBI:184982
2-(1h-imidazol-5-yl)-n-methylethanamine
n-[2-(1h-imidazol-5-yl)ethyl]-n-methylamine
FT-0632781
AKOS015906002
imidazole, 4(or 5)-(2-(methylamino)ethyl)-
1h-imidazole-5-ethanamine, n-methyl-
n.alpha.-methylhistamine
2-(1h-imidazol-4-yl)-n-methylethanamine
4-(2-(n-methylamino)ethyl)imidazole
n'-methylhistamine
4-(2-methylaminoethyl)-1h-imidazole
SCHEMBL119179
SCHEMBL2086409
n(sup .alpha.)-methylhistamine
PHSPJQZRQAJPPF-UHFFFAOYSA-N
n-[2-(1h-imidazol-4-yl)ethyl]-n-methylamine #
imidazole, 4-[2-(methylamino)ethyl]-
DTXSID00217671
phosphorustribromide
Q27078066
EN300-170734
[2-(1h-imidazol-4-yl)ethyl](methyl)amine
n-alpha-methylhistamine-dihydrochloride
n-methyl-1h-imidazole-4-ethanamine
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aralkylamineAn alkylamine in which the alkyl group is substituted by an aromatic group.
[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 (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Microtubule-associated protein tauHomo sapiens (human)Potency0.07940.180013.557439.8107AID1468
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency39.81070.011212.4002100.0000AID1030
regulator of G-protein signaling 4Homo sapiens (human)Potency1.19170.531815.435837.6858AID504845
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency22.38720.251215.843239.8107AID504327
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histamine H3 receptorMus musculus (house mouse)Ki0.01900.00060.01810.0680AID426166
Histamine H4 receptorHomo sapiens (human)Ki0.31610.00060.478710.0000AID1798265; AID548981
Histamine H3 receptorHomo sapiens (human)Ki0.00400.00010.33998.5110AID1798266; 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)0.79430.00740.601610.0000AID548993
Histamine H3 receptorHomo sapiens (human)EC50 (µMol)0.00040.00000.09473.1623AID548991
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
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 (3)

Processvia Protein(s)Taxonomy
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 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 (22)

Assay IDTitleYearJournalArticle
AID1346055Human H4 receptor (Histamine receptors)2001Molecular pharmacology, Mar, Volume: 59, Issue:3
Cloning, expression, and pharmacological characterization of a novel human histamine receptor.
AID1346088Mouse H3 receptor (Histamine receptors)2003European journal of pharmacology, Apr-25, Volume: 467, Issue:1-3
Molecular and pharmacological characterization of the mouse histamine H3 receptor.
AID1346055Human H4 receptor (Histamine receptors)2001The Journal of pharmacology and experimental therapeutics, Mar, Volume: 296, Issue:3
Cloning and characterization of a novel human histamine receptor.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID548997Selectivity ratio of EC50 for human histamine H4 receptor to EC50 for human histamine H3 receptor2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
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.
AID408549Agonist activity at histamine H3 receptor in guinea pig ileum assessed as inhibition of electrically induced twitch contraction2008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
4-benzyl-1H-imidazoles with oxazoline termini as histamine H3 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.
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?
AID89730Binding affinity for Histamine H3 receptor1999Journal of medicinal chemistry, Apr-08, Volume: 42, Issue:7
Synthesis and in vitro pharmacology of a series of new chiral histamine H3-receptor ligands: 2-(R and S)-Amino-3-(1H-imidazol-4(5)-yl)propyl ether derivatives.
AID426166Displacement of 3-([1,1,1-3H]methyl)-2-(4-{[3-(1-pyrrolidinyl)propyl]oxy}phenyl)-4(3H)-quinazolinone from mouse histamine H3 receptor expressed in HEK293 cells2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
Development of a selective and potent radioactive ligand for histamine H(3) receptors: A compound potentially useful for receptor occupancy studies.
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.
AID408554Activity at histamine H3 receptor in guinea pig ileum2008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
4-benzyl-1H-imidazoles with oxazoline termini as histamine H3 receptor agonists.
AID197186Evaluated for inhibition of [3H]histamine release from preloaded slices and is represented as pD2.1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Histamine H3 ligands: just pharmacological tools or potential therapeutic agents?
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.
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?
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?
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (18.18)18.2507
2000's6 (54.55)29.6817
2010's1 (9.09)24.3611
2020's2 (18.18)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 43.60

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index43.60 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.94 (4.65)
Search Engine Demand Index60.22 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (43.60)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]