Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H15N3S |
Molecular Weight | 161.268 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCCSC(N)=N
InChI
InChIKey=OLHQOJYVQUNWPL-UHFFFAOYSA-N
InChI=1S/C6H15N3S/c1-9(2)4-3-5-10-6(7)8/h3-5H2,1-2H3,(H3,7,8)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/871093
Sources: https://www.ncbi.nlm.nih.gov/pubmed/871093
Dimaprit (S-[3-(N,N-dimethylamino)propyl]isothiourea) has been shown to be a highly specific histamine H2-receptor agonist.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25524412 | https://www.ncbi.nlm.nih.gov/pubmed/21211106
Curator's Comment: Dimaprit is CNS active in animals. No human data available.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1941 |
|||
Target ID: CHEMBL3048 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10385230 |
49.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Histamine modulates the expression of c-fos through cyclic AMP production via the H2 receptor in the human promonocytic cell line U937. | 1997 Jun |
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Phe217 regulates the transfer of allosteric information across the subunit interface of the RecA protein filament. | 2001 Jan 10 |
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Disturbance of the prejunctional modulation of cholinergic neurotransmission during chronic granulomatous inflammation of the mouse ileum. | 2001 Jul |
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Cloning and characterization of a novel human histamine receptor. | 2001 Mar |
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Histamine induces exocytosis and IL-6 production from human lung macrophages through interaction with H1 receptors. | 2001 Mar 15 |
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Histamine H3 receptor-mediated inhibition of sympathetically evoked mydriasis in rats. | 2001 May 4 |
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Histamine inhibits chemotaxis, phagocytosis, superoxide anion production, and the production of TNFalpha and IL-12 by macrophages via H2-receptors. | 2001 Sep |
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Contractile response of horse deep dorsal penile vein to histamine. | 2002 Apr |
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Effects of histamine on the contractile and electrical activity in isolated lymphatic vessels of the guinea-pig mesentery. | 2002 Aug |
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Methods to enhance signal using isotopic in situ hybridization. | 2002 Aug |
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Accelerated clearance of Escherichia coli in experimental peritonitis of histamine-deficient mice. | 2002 Aug 15 |
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Activation of histamine H2 receptors ameliorates experimental allergic encephalomyelitis. | 2002 Aug 7 |
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Characteristics of histamine tachyphylaxis in rat uterine smooth muscle. | 2002 Dec |
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Further evidence for the involvement of histamine H2 receptors in the control of defensive behaviour generated in the midbrain tectum. | 2002 Feb |
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Rodent antinociception following acute treatment with different histamine receptor agonists and antagonists. | 2002 Jun |
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Influence of SKF 91488, histamine N-methyltransferase inhibitor, on the central cardiovascular regulation during controlled, stepwise hemorrhagic hypotension in rats. | 2002 May-Jun |
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Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells. | 2002 Oct |
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Histamine H(2) receptor-mediated modulation of local cytokine expression in a mouse experimental tumor model. | 2002 Oct 11 |
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Histamine receptor type coupled to nitric oxide-induced relaxation of guinea-pig nasal mucosa. | 2002 Oct-Dec |
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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 |
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Differential activation of dual signaling responses by human H1 and H2 histamine receptors. | 2003 Feb |
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Histamine inhibits lipopolysaccharide-induced tumor necrosis factor-alpha production in an intercellular adhesion molecule-1- and B7.1-dependent manner. | 2003 Feb |
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Histamine elicits neuronal excitatory response of red nucleus in the rat via H2 receptors in vitro. | 2003 Nov 6 |
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PD-136,450: a CCK2 (gastrin) receptor antagonist with antisecretory, anxiolytic and antiulcer activity. | 2003 Oct |
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Histaminergic receptors modulate the coronary vascular response in isolated guinea pig hearts. Role of nitric oxide. | 2003 Sep |
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Alleviation of ischemic neuronal damage by histamine H2 receptor stimulation in the rat striatum. | 2004 Jan 26 |
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Replacement of amino acid sequence features of a- and c-subunits of ATP synthases of Alkaliphilic Bacillus with the Bacillus consensus sequence results in defective oxidative phosphorylation and non-fermentative growth at pH 10.5. | 2004 Jun 18 |
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Involvement of histamine H4 and H1 receptors in scratching induced by histamine receptor agonists in Balb C mice. | 2004 May |
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Histamine helps development of eczematous lesions in experimental contact dermatitis in mice. | 2005 Aug |
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Curcuma longa extract protects against gastric ulcers by blocking H2 histamine receptors. | 2005 Dec |
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Histamine contributes to ischemia-related activation of cardiac spinal afferents: role of H1 receptors and PKC. | 2005 Feb |
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Histamine receptors that influence blockage of the normal human nasal airway. | 2005 Mar |
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Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro. | 2005 Nov |
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Histamine excites neonatal rat sympathetic preganglionic neurons in vitro via activation of H1 receptors. | 2006 Apr |
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Histamine enhances inhibitory avoidance memory consolidation through a H2 receptor-dependent mechanism. | 2006 Jul |
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Cultured smooth muscle cells of the human vesical sphincter are more sensitive to histamine than are detrusor smooth muscle cells. | 2006 May |
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Study on the antinociceptive action of Tyr-K-MIF-1, a peptide from the MIF family. | 2007 Apr |
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Histamine H4 receptor agonists have more activities than H4 agonism in antigen-specific human T-cell responses. | 2007 Jun |
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Histamine ameliorates anti-glomerular basement membrane antibody-induced glomerulonephritis in rats. | 2007 Sep |
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Olfactory interference during inhibitory backward pairing in honey bees. | 2008 |
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The ATPase cycle of the mitochondrial Hsp90 analog Trap1. | 2008 Apr 25 |
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The anti-secretory and anti-ulcer activities of esomeprazole in comparison with omeprazole in the stomach of rats and rabbits. | 2008 Feb |
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Validation of a conscious rat model for the discovery of novel agents that inhibit gastric acid secretion. | 2008 Jul 28 |
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Histamine-induced itch and its relationship with pain. | 2008 Jul 31 |
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Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells. | 2008 Jun 6 |
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Histamine metabolism influences blood vessel branching in zebrafish reg6 mutants. | 2008 Mar 25 |
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Cytokine responses of intraepithelial lymphocytes are regulated by histamine H(2) receptor. | 2009 |
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G-protein coupled receptor signaling architecture of mammalian immune cells. | 2009 |
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Pharmacological characterization of the new histamine H4 receptor agonist VUF 8430. | 2009 May |
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Control of the flow properties of DNA by topoisomerase II and its targeting inhibitor. | 2010 Sep 22 |
Patents
Sample Use Guides
In vitro, dimaprit dose dependently inhibited the production of TNF-alpha in mouse peritoneal macrophages and human peripheral blood monocytes stimulated with lipopolysaccharide with IC50 values of 1 uM.
Dimaprit, added to tumour cell cultures (100 uM), inhibited the incorporation of 3H-thymidine while embryonic cell cultures were unaffected.
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DIMAPRIT
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65119-89-3
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DTXSID0037154
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ZZQ699148P
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3077
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ACTIVE MOIETY