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 |
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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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Effect of adenosine and histamine receptor stimulation on canine histamine release to pentagastrin. | 1997 |
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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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Regulation of interleukin-6, and macrophage colony-stimulating factor mRNA levels by histamine in stromal cell line (MC3T3-G2/PA6). | 1998 May |
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Histamine H1 and H2 receptor antagonists accelerate skin barrier repair and prevent epidermal hyperplasia induced by barrier disruption in a dry environment. | 2001 Feb |
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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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Structure of a fast kinesin: implications for ATPase mechanism and interactions with microtubules. | 2001 Nov 15 |
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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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Accelerated clearance of Escherichia coli in experimental peritonitis of histamine-deficient mice. | 2002 Aug 15 |
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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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Comparison of the antisecretory and antiulcer activity of epidermal growth factor, urogastrone and transforming growth factor alpha and its derivative in rodents in vivo. | 2002 Jul |
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Rodent antinociception following acute treatment with different histamine receptor agonists and antagonists. | 2002 Jun |
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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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Excitatory effects of histamine on cerebellar interpositus nuclear cells of rats through H(2) receptors in vitro. | 2002 Sep 6 |
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Histaminergic modulation of the intact respiratory network of adult mice. | 2003 Feb |
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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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The effects of histamine on rat and monkey retinal ganglion cells. | 2004 Nov-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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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 |
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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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Modification of formalin-induced nociception by different histamine receptor agonists and antagonists. | 2007 Jan 15 |
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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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Pharmacological characterization of the new histamine H4 receptor agonist VUF 8430. | 2009 May |
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Differential role of beta-catenin in VEGF and histamine-induced MMP-2 production in microvascular endothelial cells. | 2009 May 15 |
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Persistent oxygen-glucose deprivation induces astrocytic death through two different pathways and calpain-mediated proteolysis of cytoskeletal proteins during astrocytic oncosis. | 2010 Jul 26 |
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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