Page last updated: 2024-12-11

(2S)-1-(1H-imidazol-5-yl)-2-propanamine

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

(2S)-1-(1H-imidazol-5-yl)-2-propanamine is a synthetic compound that is a **potent and selective inhibitor** of **histamine H3 receptors (H3R)**.

Here's a breakdown:

* **(2S)-1-(1H-imidazol-5-yl)-2-propanamine** is the chemical name.
* **H3R** are a type of histamine receptor located in the brain and other tissues.
* **Inhibitors** block the action of a receptor.

**Why is it important for research?**

H3R plays a crucial role in the regulation of various functions in the central nervous system (CNS), including:

* **Wakefulness and sleep:** H3R activation promotes sleep and reduces wakefulness.
* **Cognitive function:** H3R antagonists (like this compound) may enhance cognitive function by promoting wakefulness and improving attention.
* **Neuroinflammation:** H3R antagonists have shown potential in reducing neuroinflammation.
* **Pain perception:** H3R antagonists may have analgesic properties.

**Research on (2S)-1-(1H-imidazol-5-yl)-2-propanamine and other H3R inhibitors is focused on developing new therapeutic agents for:**

* **Treating sleep disorders like insomnia**
* **Enhancing cognitive function in conditions like Alzheimer's disease**
* **Treating neuroinflammatory conditions**
* **Developing new analgesics**

This compound, due to its selectivity and potency, serves as a valuable tool in understanding the role of H3R in these physiological processes and could be a stepping stone in the development of new H3R-targeted medications.

Cross-References

ID SourceID
PubMed CID6603865
CHEMBL ID11919
CHEBI ID125525
SCHEMBL ID4008535

Synonyms (27)

Synonym
(2s)-1-(3h-imidazol-4-yl)propan-2-amine
gtpl1238
(s)-alpha-meha
(s)-alpha-methylhistamine
bdbm22905
(2s)-1-(1h-imidazol-5-yl)propan-2-amine
tocris-0572
NCGC00015491-01
lopac-h-128
NCGC00024659-01
NCGC00024659-02
PDSP2_000540
PDSP1_000509
CHEBI:125525
CHEMBL11919 ,
SCHEMBL4008535
bdbm81972
alpha-methylhistamine-s
cas_75614-93-6
AKOS006339244
BRD-K28308851-001-01-8
DTXSID10662759
(2s)-1-(1h-imidazol-4-yl)-2-propanamine
bdbm50472559
alpha-methylhistamine-dihydrobromide-(s)-(+)
(s)-2-(1h-imidazol-4-yl)-1-methyl-ethylamine
EN300-1817457
[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 (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
NFKB1 protein, partialHomo sapiens (human)Potency12.58930.02827.055915.8489AID895; AID928
ThrombopoietinHomo sapiens (human)Potency10.00000.02517.304831.6228AID917; AID918
[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 H4 receptorHomo sapiens (human)Ki3.98100.00060.478710.0000AID1798265; AID548981
Histamine H3 receptorHomo sapiens (human)Ki0.53650.00010.33998.5110AID1798266; AID1829881; AID1829899; 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)12.58920.00740.601610.0000AID548993
Histamine H3 receptorHomo sapiens (human)EC50 (µMol)0.01000.00000.09473.1623AID548991
[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 (20)

Assay IDTitleYearJournalArticle
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.
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.
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.
AID89872Affinity for histamine H3 receptor in rat cerebral cortex.1999Journal 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.
AID1829881Binding affinity in Nluc-hH3R assessed in HEK293 cells by NanoBRET binding assay2021Journal of medicinal chemistry, 08-12, Volume: 64, Issue:15
A Versatile Sub-Nanomolar Fluorescent Ligand Enables NanoBRET Binding Studies and Single-Molecule Microscopy at the Histamine H
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.
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?
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.
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?
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.
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?
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.
AID1829899Binding affinity in Nluc-hH3R assessed in HEK293T cells by NanoBRET binding assay2021Journal of medicinal chemistry, 08-12, Volume: 64, Issue:15
A Versatile Sub-Nanomolar Fluorescent Ligand Enables NanoBRET Binding Studies and Single-Molecule Microscopy at the Histamine H
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.
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.
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.
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.
AID1346017Rat H3 receptor (Histamine receptors)2002European journal of pharmacology, Oct-18, Volume: 453, Issue:1
Characteristics of recombinantly expressed rat and human histamine H3 receptors.
AID1346107Human H3 receptor (Histamine receptors)2002European journal of pharmacology, Oct-18, Volume: 453, Issue:1
Characteristics of recombinantly expressed rat and human histamine H3 receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (22.22)18.2507
2000's3 (33.33)29.6817
2010's1 (11.11)24.3611
2020's3 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.71

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 Index12.71 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index5.01 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.71)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (11.11%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]