4-METHYLHISTAMINE

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 Search

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

Primary Target	Pharmacology	Condition	Potency
Histamine H4 receptor 20 Target ID: CHEMBL3759 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21044842	Agonist 2678		31.62 nM [EC50]

PubMed

Title	Date	PubMed
Effects of histamine and related compounds on the differentiation of HL-60-Eo cells into eosinophils.	2001 Sep	11771852
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 Jan	11752121
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding.	2002 Jun	12065605
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 Sep 27	12364868
Histamine inhibits lipopolysaccharide-induced tumor necrosis factor-alpha production in an intercellular adhesion molecule-1- and B7.1-dependent manner.	2003 Feb	12538815
Histamine downregulates CD14 expression via H2 receptors on human monocytes.	2003 Sep	14499251
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 Sep	15947036
Compared pharmacology of human histamine H3 and H4 receptors: structure-activity relationships of histamine derivatives.	2006 Apr	16432504
Histamine downregulates monocyte CCL2 production through the histamine H4 receptor.	2007 Aug	17507084
Histamine H4 receptor agonists have more activities than H4 agonism in antigen-specific human T-cell responses.	2007 Jun	17346280
Histamine 4 receptor activation induces recruitment of FoxP3+ T cells and inhibits allergic asthma in a murine model.	2007 Jun 15	17548646
Histamine excites neurones in the human submucous plexus through activation of H1, H2, H3 and H4 receptors.	2007 Sep 1	17627982
Comparison of the effect of 4-methyl histamine on human and mouse basophil activation.	2008	18345511
Confirmation of biological effects of high dilutions. Effects of submolecular concentrations of histamine and 1-, 3- and 4-methylhistamines on human basophil activation.	2008	18345504
Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells.	2008 Jun 6	18538007
Role of histamine H(4) receptor in allergic conjunctivitis in mice.	2009 Apr 17	19249296
The histamine H4 receptor is functionally expressed on T(H)2 cells.	2009 Mar	19281909
Pharmacological characterization of the new histamine H4 receptor agonist VUF 8430.	2009 May	19413569
Inhibition of basophil activation by histamine: a sensitive and reproducible model for the study of the biological activity of high dilutions.	2009 Oct	19945674
Histamine inhibits advanced glycation end products-induced adhesion molecule expression on human monocytes.	2009 Sep	19567778
Synthesis and structural and pharmacological properties of cyclopropane-based conformationally restricted analogs of 4-methylhistamine as histamine H3/H4 receptor ligands.	2010 Feb	20045649
Histamine inhibits adhesion molecule expression in human monocytes, induced by advanced glycation end products, during the mixed lymphocyte reaction.	2010 Jul	20590628
Histamine H(4) receptor antagonist ameliorates chronic allergic contact dermatitis induced by repeated challenge.	2010 Mar	19886918
Molecular determinants of ligand binding to H4R species variants.	2010 May	20103609
The effect of intracerebroventricular injection of histamine in visceral nociception induced by acetic acid in rats.	2010 Oct	21206620

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:58:31 GMT 2023` Edited by `admin` on `Fri Dec 15 18:58:31 GMT 2023`
Record UNII	54ST71P9EE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

4-METHYLHISTAMINE

Systematic 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

5(4)-METHYLHISTAMINE

Common Name

English

Code System Code Type Description

CAS

36507-31-0