Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H24N4S |
| Molecular Weight | 292.443 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
S=C(NC1CCCCC1)N2CCC(CC2)C3=CNC=N3
InChI
InChIKey=QKDDJDBFONZGBW-UHFFFAOYSA-N
InChI=1S/C15H24N4S/c20-15(18-13-4-2-1-3-5-13)19-8-6-12(7-9-19)14-10-16-11-17-14/h10-13H,1-9H2,(H,16,17)(H,18,20)
| Molecular Formula | C15H24N4S |
| Molecular Weight | 292.443 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22918191 | https://www.ncbi.nlm.nih.gov/pubmed/16432504
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22918191 | https://www.ncbi.nlm.nih.gov/pubmed/16432504
Thioperamide is an antihistamine at H3 and H4 receptors. Thioperamide behaves as both antagonist and inverse agonist.Thioperamide is under preclinical development with Glaxo Wellcome (UK) for the treatment of short-term memory impairment. It has also demonstrated antiarrhythmic effects in preclinical trials. Active development of thioperamide appears to have been discontinued.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Critical role of L-selectin and histamine H4 receptor in zymosan-induced neutrophil recruitment from the bone marrow: comparison with carrageenan. | 2004-07 |
|
| Involvement of histamine H4 and H1 receptors in scratching induced by histamine receptor agonists in Balb C mice. | 2004-05 |
|
| Histamine h3 receptor antagonists potentiate methamphetamine self-administration and methamphetamine-induced accumbal dopamine release. | 2004-04 |
|
| Thioperamide-elicited increase of histamine release from basolateral amygdala of freely moving rats and its therapeutic implications. | 2004-03 |
|
| Pruritus-associated response mediated by cutaneous histamine H3 receptors. | 2004-03 |
|
| Role of histamine receptors in the regulation of edema and circulation postburn. | 2003-12 |
|
| Critical role of histamine H4 receptor in leukotriene B4 production and mast cell-dependent neutrophil recruitment induced by zymosan in vivo. | 2003-12 |
|
| Possible role of L-carnosine in the regulation of blood glucose through controlling autonomic nerves. | 2003-11 |
|
| Histamine induces cytoskeletal changes in human eosinophils via the H(4) receptor. | 2003-11 |
|
| Generation and characterization of highly constitutive active histamine H3 receptors. | 2003-10 |
|
| Aminergic control of high-frequency (approximately 200 Hz) network oscillations in the hippocampus of the behaving rat. | 2003-09-11 |
|
| Central endogenous histamine modulates sympathetic outflow through H3 receptors in the conscious rabbit. | 2003-07 |
|
| Antinociceptive mechanisms of orally administered decursinol in the mouse. | 2003-06-13 |
|
| Activation of spinal histamine H3 receptors inhibits mechanical nociception. | 2003-06-06 |
|
| H3 receptor blockade by thioperamide enhances cognition in rats without inducing locomotor sensitization. | 2003-06 |
|
| Histamine H4 receptor mediates chemotaxis and calcium mobilization of mast cells. | 2003-06 |
|
| Two novel and selective nonimidazole histamine H3 receptor antagonists A-304121 and A-317920: I. In vitro pharmacological effects. | 2003-06 |
|
| Two novel and selective nonimidazole H3 receptor antagonists A-304121 and A-317920: II. In vivo behavioral and neurophysiological characterization. | 2003-06 |
|
| Regulation by prostaglandin E2 and histamine of angiogenesis in inflammatory granulation tissue. | 2003-05 |
|
| Histamine-induced chloride secretion is mediated via H2-receptors in the pig proximal colon. | 2003-02 |
|
| Histaminergic modulation of the intact respiratory network of adult mice. | 2003-02 |
|
| Histamine inhibits lipopolysaccharide-induced tumor necrosis factor-alpha production in an intercellular adhesion molecule-1- and B7.1-dependent manner. | 2003-02 |
|
| Replacement of imidazole by a piperidine moiety differentially affects the potency of histamine H3-receptor antagonists. | 2003-01 |
|
| Functional identification of epithelial and smooth muscle histamine-dependent relaxing mechanisms in the bovine trachea, but not in bronchi. | 2003-01 |
|
| Neuroimmune interactions in guinea pig stomach and small intestine. | 2003-01 |
|
| High-frequency oscillation in the hippocampus of the behaving rat and its modulation by the histaminergic system. | 2003 |
|
| Identification of a histamine H4 receptor on human eosinophils--role in eosinophil chemotaxis. | 2002-12-31 |
|
| Targeted disruption of H3 receptors results in changes in brain histamine tone leading to an obese phenotype. | 2002-12 |
|
| Endogenous central histamine-induced reversal of critical haemorrhagic hypotension in rats--studies with histamine N-methyltransferase inhibitor SKF 91488. | 2002-11 |
|
| Activation of the extraneuronal monoamine transporter (EMT) from rat expressed in 293 cells. | 2002-11 |
|
| Coordination of histamine H3 receptor antagonists with human adrenal cytochrome P450 enzymes. | 2002-11 |
|
| Influence of SKF 91488, histamine N-methyltransferase inhibitor, on the central cardiovascular regulation during controlled, stepwise hemorrhagic hypotension in rats. | 2002-10-26 |
|
| Characteristics of recombinantly expressed rat and human histamine H3 receptors. | 2002-10-18 |
|
| Histamine H3 receptor activation inhibits neurogenic sympathetic vasoconstriction in porcine nasal mucosa. | 2002-10-11 |
|
| Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells. | 2002-10 |
|
| Behavioral characterization of mice lacking histamine H(3) receptors. | 2002-08 |
|
| Different role of the histamine H3-receptor in vagal-, betanechol-, pentagastrin-induced gastric acid secretion in anaesthetized rats. | 2002-07 |
|
| Betahistine dihydrochloride interaction with the histaminergic system in the cat: neurochemical and molecular mechanisms. | 2002-06-20 |
|
| Rodent antinociception following acute treatment with different histamine receptor agonists and antagonists. | 2002-06 |
|
| Differential in vivo effects of H3 receptor ligands in a new mouse dipsogenia model. | 2002-06 |
|
| Modulation of the discriminative stimulus effects of cocaine and methamphetamine by the histaminergic system. | 2002-06 |
|
| Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding. | 2002-06 |
|
| Effects of N-alpha-methyl-histamine on human H(2) receptors expressed in CHO cells. | 2002-06 |
|
| Endogenous histamine in the medial septum-diagonal band complex increases the release of acetylcholine from the hippocampus: a dual-probe microdialysis study in the freely moving rat. | 2002-05 |
|
| Role of histamine H3 receptors in control of mouse intestinal motility in vivo and in vitro: comparison with alpha2-adrenoceptors. | 2002-05 |
|
| Contribution of the histaminergic receptor subtypes to histamine-induced cerebellar granular neurotoxicity. | 2002-04-23 |
|
| Contractile response of horse deep dorsal penile vein to histamine. | 2002-04 |
|
| Effects of histidine, a precursor of histamine, on pentylenetetrazole-induced seizures in rats. | 2002-04 |
|
| Muscarinic, adenosine A(2) and histamine H(3) receptor modulation of haloperidol-induced c-fos expression in the striatum and nucleus accumbens. | 2002 |
|
| Characterisation of the calcium responses to histamine in capsaicin-sensitive and capsaicin-insensitive sensory neurones. | 2002 |
Sample Use Guides
mouse: thioperamide (10 μg, i.c.v.).
rat: thioperamide (20, 50 μg, i.c.v.).
rat: thioperamide (310 µg/kg, i.v.).
mouse: thioperamide (10 mg/kg, i.p.)
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:51:35 GMT 2025
by
admin
on
Mon Mar 31 19:51:35 GMT 2025
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| Record UNII |
II4319BWUI
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| Record Status |
Validated (UNII)
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| Record Version |
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3035905
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II4319BWUI
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DTXSID50147555
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Thioperamide
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106243-16-7
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admin on Mon Mar 31 19:51:35 GMT 2025 , Edited by admin on Mon Mar 31 19:51:35 GMT 2025
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