IMETIT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H10N4S
Molecular Weight	170.235
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=N)SCCC1=CN=CN1

InChI

InChIKey=PEHSVUKQDJULKE-UHFFFAOYSA-N

InChI=1S/C6H10N4S/c7-6(8)11-2-1-5-3-9-4-10-5/h3-4H,1-2H2,(H3,7,8)(H,9,10)

HIDE SMILES / InChI

Description
Sources: https://www.sciencedirect.com/science/article/pii/0223523492901854 | https://www.ncbi.nlm.nih.gov/pubmed/1383495

Imetit (S-[2-(4-(imidazolyl)ethyl]isothiourea) is a highly specific and potent histamine H3 receptor agonist. It is widely used to study H3-mediated signaling.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H3 receptor 44 Target ID: CHEMBL264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8114949 \| https://www.ncbi.nlm.nih.gov/pubmed/20688049 \| https://www.ncbi.nlm.nih.gov/pubmed/1383495	Agonist 2678		0.45 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Allergic rhinitis 100 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21055323 https://www.ncbi.nlm.nih.gov/pubmed/20806863	Primary	Preclinical	Unknown Approved Use Unknown
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16954192	Primary	Preclinical	Unknown Approved Use Unknown
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16532454	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibitory H3 receptors on sympathetic nerves of the pithed rat: activation by endogenous histamine and operation in spontaneously hypertensive rats.	1997 Feb	9050021
Genomic organization and characterization of splice variants of the human histamine H3 receptor.	2001 Apr 15	11284713
Histaminergic modulation of GABAergic transmission in rat ventromedial hypothalamic neurones.	2001 Aug 1	11483709
Constitutive activity of histamine h(3) receptors stably expressed in SK-N-MC cells: display of agonism and inverse agonism by H(3) antagonists.	2001 Dec	11714875
Cloning and characterization of a novel human histamine receptor.	2001 Mar	11181941
Cloning and pharmacological characterization of a fourth histamine receptor (H(4)) expressed in bone marrow.	2001 Mar	11179434
Pharmacological analysis of immepip and imetit homologues. Further evidence for histamine H(3) receptor heterogeneity?	2001 Oct 15	11640964
Histamine H3-receptor-mediated [35S]GTP gamma[S] binding: evidence for constitutive activity of the recombinant and native rat and human H3 receptors.	2002 Jan	11815373
Presynaptic H3 autoreceptors modulate histamine synthesis through cAMP pathway.	2002 Jan	11752226
Rodent antinociception following acute treatment with different histamine receptor agonists and antagonists.	2002 Jun	12175473
Molecular cloning and pharmacology of functionally distinct isoforms of the human histamine H(3) receptor.	2002 Jun	12069903
The role of transmembrane helix 5 in agonist binding to the human H3 receptor.	2002 May	11961043
Characteristics of recombinantly expressed rat and human histamine H3 receptors.	2002 Oct 18	12393057
Histaminergic modulation of the intact respiratory network of adult mice.	2003 Feb	12634928
Generation and characterization of highly constitutive active histamine H3 receptors.	2003 Oct	12954820
Involvement of histamine H4 and H1 receptors in scratching induced by histamine receptor agonists in Balb C mice.	2004 May	15066908
Cloning and expression of the mouse histamine H3 receptor: evidence for multiple isoforms.	2004 Sep	15341517
H3 autoreceptors modulate histamine synthesis through calcium/calmodulin- and cAMP-dependent protein kinase pathways.	2005 Jan	15465923
G protein-dependent pharmacology of histamine H3 receptor ligands: evidence for heterogeneous active state receptor conformations.	2005 Jul	15821027
Regulation of norepinephrine release from isolated bovine irides by histamine.	2006 Jul	16804758
Histamine H3-receptor signaling in cardiac sympathetic nerves: Identification of a novel MAPK-PLA2-COX-PGE2-EP3R pathway.	2007 Apr 15	17266940
Interactions between histamine H3 and dopamine D2 receptors and the implications for striatal function.	2008 Aug	18547596
Cloning and characterization of the monkey histamine H3 receptor isoforms.	2008 Dec 28	18977214
Histamine depolarizes neurons in the dorsal vagal complex.	2008 Feb 13	18162318
Distinctive role of central histamine H3 receptor in various orexigenic pathways.	2008 Jan 28	18037404
Participation of histamine H3 receptors in experimental allergic rhinitis of mice.	2008 Oct	18845911
Effects of histamine H(3) receptor activation on the behavioral-stimulant effects of methamphetamine and cocaine in mice and squirrel monkeys.	2009	19145102
The role of histamine 3 receptors in the control of food intake in a seasonal model of obesity: the Siberian hamster.	2009 Mar	19339875
Comparison of the pharmacological properties of human and rat histamine H(3)-receptors.	2010 Nov 1	20688049
Molecular determinants of ligand binding modes in the histamine H(4) receptor: linking ligand-based three-dimensional quantitative structure-activity relationship (3D-QSAR) models to in silico guided receptor mutagenesis studies.	2011 Dec 8	22003888

Patents

Sample Use Guides

In Vivo Use Guide

mice: 10 mg/kg i.p. rats: 5 or 10 mg/kg i.p. rsts: 10 umol/kg i.a rats: 10 nmol/side (injection into basolateral amygdala) rats: 10 ug/side (injection into hippocampus)

Route of Administration: Other

In Vitro Use Guide

Imetit (EC50 25 nm) could mimic histamine effect in inducing eosinophil shape change.

Name

Type

Language

IMETIT

Common Name

English

2-(1H-IMIDAZOL-5-YL)ETHYL IMIDOTHIOCARBAMATE

Systematic Name

English

Code System Code Type Description

FDA UNII

677MJ4VPZC