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Details

Stereochemistry ACHIRAL
Molecular Formula C6H11N3
Molecular Weight 125.1716
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-METHYLHISTAMINE

SMILES

CC1=C(CCN)NC=N1

InChI

InChIKey=UGYXPZQILZRKJJ-UHFFFAOYSA-N
InChI=1S/C6H11N3/c1-5-6(2-3-7)9-4-8-5/h4H,2-3,7H2,1H3,(H,8,9)

HIDE SMILES / InChI

Molecular Formula C6H11N3
Molecular Weight 125.1716
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
31.62 nM [EC50]
PubMed

PubMed

TitleDatePubMed
The effect of intracerebroventricular injection of histamine in visceral nociception induced by acetic acid in rats.
2010-10
Histamine inhibits adhesion molecule expression in human monocytes, induced by advanced glycation end products, during the mixed lymphocyte reaction.
2010-07
Molecular determinants of ligand binding to H4R species variants.
2010-05
Histamine H(4) receptor antagonist ameliorates chronic allergic contact dermatitis induced by repeated challenge.
2010-03
Synthesis and structural and pharmacological properties of cyclopropane-based conformationally restricted analogs of 4-methylhistamine as histamine H3/H4 receptor ligands.
2010-02
Inhibition of basophil activation by histamine: a sensitive and reproducible model for the study of the biological activity of high dilutions.
2009-10
Histamine inhibits advanced glycation end products-induced adhesion molecule expression on human monocytes.
2009-09
Pharmacological characterization of the new histamine H4 receptor agonist VUF 8430.
2009-05
Role of histamine H(4) receptor in allergic conjunctivitis in mice.
2009-04-17
The histamine H4 receptor is functionally expressed on T(H)2 cells.
2009-03
Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells.
2008-06-06
Comparison of the effect of 4-methyl histamine on human and mouse basophil activation.
2008
Confirmation of biological effects of high dilutions. Effects of submolecular concentrations of histamine and 1-, 3- and 4-methylhistamines on human basophil activation.
2008
Histamine excites neurones in the human submucous plexus through activation of H1, H2, H3 and H4 receptors.
2007-09-01
Histamine downregulates monocyte CCL2 production through the histamine H4 receptor.
2007-08
Histamine 4 receptor activation induces recruitment of FoxP3+ T cells and inhibits allergic asthma in a murine model.
2007-06-15
Histamine H4 receptor agonists have more activities than H4 agonism in antigen-specific human T-cell responses.
2007-06
Compared pharmacology of human histamine H3 and H4 receptors: structure-activity relationships of histamine derivatives.
2006-04
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.
2005-09
Histamine downregulates CD14 expression via H2 receptors on human monocytes.
2003-09
Histamine inhibits lipopolysaccharide-induced tumor necrosis factor-alpha production in an intercellular adhesion molecule-1- and B7.1-dependent manner.
2003-02
Effect of histamine on intercellular adhesion molecule-1 expression and production of interferon-gamma and interleukin-12 in mixed lymphocyte reaction stimulated with interleukin-18.
2002-09-27
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding.
2002-06
Histamine regulation of interleukin-18-initiating cytokine cascade is associated with down-regulation of intercellular adhesion molecule-1 expression in human peripheral blood mononuclear cells.
2002-01
Effects of histamine and related compounds on the differentiation of HL-60-Eo cells into eosinophils.
2001-09
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:28:13 GMT 2025
Edited
by admin
on Mon Mar 31 19:28:13 GMT 2025
Record UNII
54ST71P9EE
Record Status Validated (UNII)
Record Version
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Name Type Language
4-METHYLHISTAMINE
Systematic Name English
5(4)-METHYLHISTAMINE
Preferred Name English
1H-IMIDAZOLE-4-ETHANAMINE, 5-METHYL-
Systematic Name English
4-(2-AMINOETHYL)-5-METHYLIMIDAZOLE
Systematic Name English
2-(5-METHYL-4-IMIDAZOLYL)ETHYLAMINE
Systematic Name English
1H-IMIDAZOLE-5-ETHANAMINE, 4-METHYL-
Systematic Name English
5-(2-AMINOETHYL)-4-METHYLIMIDAZOLE
Systematic Name English
Code System Code Type Description
CAS
36507-31-0
Created by admin on Mon Mar 31 19:28:13 GMT 2025 , Edited by admin on Mon Mar 31 19:28:13 GMT 2025
PRIMARY
PUBCHEM
37463
Created by admin on Mon Mar 31 19:28:13 GMT 2025 , Edited by admin on Mon Mar 31 19:28:13 GMT 2025
PRIMARY
MESH
C025566
Created by admin on Mon Mar 31 19:28:13 GMT 2025 , Edited by admin on Mon Mar 31 19:28:13 GMT 2025
PRIMARY
EPA CompTox
DTXSID90957812
Created by admin on Mon Mar 31 19:28:13 GMT 2025 , Edited by admin on Mon Mar 31 19:28:13 GMT 2025
PRIMARY
FDA UNII
54ST71P9EE
Created by admin on Mon Mar 31 19:28:13 GMT 2025 , Edited by admin on Mon Mar 31 19:28:13 GMT 2025
PRIMARY
WIKIPEDIA
4-METHYLHISTAMINE
Created by admin on Mon Mar 31 19:28:13 GMT 2025 , Edited by admin on Mon Mar 31 19:28:13 GMT 2025
PRIMARY