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

Molecular Formula	C6H10N4S
Molecular Weight	170.235
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 46 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 2752		0.45 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Allergic rhinitis 104 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21055323 https://www.ncbi.nlm.nih.gov/pubmed/20806863	Primary	Preclinical	Unknown Approved Use Unknown
Obesity 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16954192	Primary	Preclinical	Unknown Approved Use Unknown
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16532454	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
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.	2011-12-08	22003888
Involvement of histaminergic receptor mechanisms in the stimulation of NT-3 synthesis in astrocytes.	2011-06	21276809
Comparison of the pharmacological properties of human and rat histamine H(3)-receptors.	2010-11-01	20688049
[Substance P and its receptors are involved in the effect of histamine H3 receptor agonist, IMETIT on nasal allergic symptoms in guinea pigs].	2010-06	21055323
[Effect of H3R agonist, IMETIT on allergic rhinitis in guinea pigs].	2010-06	20806863
Different role of cAMP dependent protein kinase and CaMKII in H3 receptor regulation of histamine synthesis and release.	2009-12-15	19735700
Pharmacologic attenuation of pelvic pain in a murine model of interstitial cystitis.	2009-11-12	19909543
The ameliorating effects of NMDA receptor agonists on histamine H1 antagonist-induced memory and hippocampal theta disruptions are prevented by the H3 receptor agonist in rats.	2009-08-14	19463907
Urethane, but not pentobarbitone, attenuates presynaptic receptor function in rats: a contribution to the choice of anaesthetic.	2009-08	19681871
JNJ-10181457, a selective non-imidazole histamine H(3) receptor antagonist, normalizes acetylcholine neurotransmission and has efficacy in translational rat models of cognition.	2009-06	19345233
The role of histamine 3 receptors in the control of food intake in a seasonal model of obesity: the Siberian hamster.	2009-03	19339875
Effects of histamine H(3) receptor activation on the behavioral-stimulant effects of methamphetamine and cocaine in mice and squirrel monkeys.	2009	19145102
Cloning and characterization of the monkey histamine H3 receptor isoforms.	2008-12-28	18977214
Participation of histamine H3 receptors in experimental allergic rhinitis of mice.	2008-10	18845911
Interactions between histamine H3 and dopamine D2 receptors and the implications for striatal function.	2008-08	18547596
Autoregulation of McA-RH7777 hepatoma cell proliferation by histamine H3 receptors.	2008-08	18474684
Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells.	2008-06-06	18538007
Histamine H(3) receptor ligands modulate L-dopa-evoked behavioral responses and L-dopa derived extracellular dopamine in dopamine-denervated rat striatum.	2008-06-05	18522902
Histamine depolarizes neurons in the dorsal vagal complex.	2008-02-13	18162318
Distinctive role of central histamine H3 receptor in various orexigenic pathways.	2008-01-28	18037404
Histamine H3-receptor signaling in cardiac sympathetic nerves: Identification of a novel MAPK-PLA2-COX-PGE2-EP3R pathway.	2007-04-15	17266940
Modification of formalin-induced nociception by different histamine receptor agonists and antagonists.	2007-01-15	16631358
Histamine H3 receptor agonist- and antagonist-evoked vacuous chewing movements in 6-OHDA-lesioned rats occurs in an absence of change in microdialysate dopamine levels.	2006-12-15	17055481
Histamine decreases myogenic tone in rat cerebral arteries by H2-receptor-mediated KV channel activation, independent of endothelium and cyclic AMP.	2006-10-10	16920098
Homologous down-regulation of histamine H3 receptors in rat striatal slices.	2006-08	16715497
Regulation of norepinephrine release from isolated bovine irides by histamine.	2006-07	16804758
Histamine H3 receptor agonists reduce L-dopa-induced chorea, but not dystonia, in the MPTP-lesioned nonhuman primate model of Parkinson's disease.	2006-06	16532454
Histamine excites neonatal rat sympathetic preganglionic neurons in vitro via activation of H1 receptors.	2006-04	16354729
G protein-dependent pharmacology of histamine H3 receptor ligands: evidence for heterogeneous active state receptor conformations.	2005-07	15821027
Significance of Conversation between Mast Cells and Nerves.	2005-06-15	20529227
H3 autoreceptors modulate histamine synthesis through calcium/calmodulin- and cAMP-dependent protein kinase pathways.	2005-01	15465923
Histamine H3 receptors modulate reactive hyperemia in rat gut.	2004-09	15381834
Cloning and expression of the mouse histamine H3 receptor: evidence for multiple isoforms.	2004-09	15341517
Histamine H4 receptor mediates eosinophil chemotaxis with cell shape change and adhesion molecule upregulation.	2004-05	15131002
Involvement of histamine H4 and H1 receptors in scratching induced by histamine receptor agonists in Balb C mice.	2004-05	15066908
Involvement of central and peripheral histamine H(3) receptors in the control of the vascular tone and oxygen uptake in the mesenteric circulation of the rat.	2004-03	15082882
Role of histamine receptors in the regulation of edema and circulation postburn.	2003-12	14636750
Histamine induces cytoskeletal changes in human eosinophils via the H(4) receptor.	2003-11	14530216
Generation and characterization of highly constitutive active histamine H3 receptors.	2003-10	12954820
Waking selective neurons in the posterior hypothalamus and their response to histamine H3-receptor ligands: an electrophysiological study in freely moving cats.	2003-09-15	12946612
An in vitro study of histamine on the pulmonary artery of the Wistar-Kyoto and spontaneously hypertensive rats.	2003-05-30	12787830
Molecular and pharmacological characterization of the mouse histamine H3 receptor.	2003-04-25	12706455
Histaminergic modulation of the intact respiratory network of adult mice.	2003-02	12634928
Characteristics of recombinantly expressed rat and human histamine H3 receptors.	2002-10-18	12393057
Functional analysis of histamine receptor subtypes involved in endothelium-mediated relaxation of the human uterine artery.	2002-08	12100006
Rodent antinociception following acute treatment with different histamine receptor agonists and antagonists.	2002-06	12175473
Molecular cloning and pharmacology of functionally distinct isoforms of the human histamine H(3) receptor.	2002-06	12069903
The role of transmembrane helix 5 in agonist binding to the human H3 receptor.	2002-05	11961043
Histamine H3-receptor-mediated [35S]GTP gamma[S] binding: evidence for constitutive activity of the recombinant and native rat and human H3 receptors.	2002-01	11815373
Inhibitory H3 receptors on sympathetic nerves of the pithed rat: activation by endogenous histamine and operation in spontaneously hypertensive rats.	1997-02	9050021

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:10:56 GMT 2025` Edited by `admin` on `Mon Mar 31 19:10:56 GMT 2025`
Record UNII	677MJ4VPZC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Imetit

Common Name

English

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

Preferred Name

English

Code System Code Type Description

FDA UNII

677MJ4VPZC