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 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
Genomic organization and characterization of splice variants of the human histamine H3 receptor.	2001 Apr 15	11284713
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 pharmacological characterization of a fourth histamine receptor (H(4)) expressed in bone marrow.	2001 Mar	11179434
Functional analysis of histamine receptor subtypes involved in endothelium-mediated relaxation of the human uterine artery.	2002 Aug	12100006
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
Characteristics of recombinantly expressed rat and human histamine H3 receptors.	2002 Oct 18	12393057
Molecular and pharmacological characterization of the mouse histamine H3 receptor.	2003 Apr 25	12706455
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
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
Cloning and characterization of the monkey histamine H3 receptor isoforms.	2008 Dec 28	18977214
Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells.	2008 Jun 6	18538007
Urethane, but not pentobarbitone, attenuates presynaptic receptor function in rats: a contribution to the choice of anaesthetic.	2009 Aug	19681871
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 Aug 14	19463907
Involvement of histaminergic receptor mechanisms in the stimulation of NT-3 synthesis in astrocytes.	2011 Jun	21276809

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 `Fri Dec 15 18:20:31 GMT 2023` Edited by `admin` on `Fri Dec 15 18:20:31 GMT 2023`
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

Systematic Name

English

Code System Code Type Description

FDA UNII

677MJ4VPZC