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 |
|---|---|---|
| Role of central histaminergic system in lorazepam withdrawal syndrome in rats. | 2001 Apr |
|
| Histamine and selective H3-receptor ligands: a possible role in the mechanism and management of epilepsy. | 2001 Apr |
|
| Cognitive enhancing properties of thioperamide infused into the nucleus basalis magnocellularis of the rat. | 2001 Apr |
|
| Histaminergic modulation of GABAergic transmission in rat ventromedial hypothalamic neurones. | 2001 Aug 1 |
|
| 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 |
|
| [Identification and characterization of histamine H4 receptor]. | 2001 Jul |
|
| Novel histaprodifen analogues as potent histamine H1-receptor agonists in the pithed and in the anaesthetized rat. | 2001 Jul |
|
| Disturbance of the prejunctional modulation of cholinergic neurotransmission during chronic granulomatous inflammation of the mouse ileum. | 2001 Jul |
|
| Effects of histamine H3-receptor ligands on brain monoamine oxidase in various mammalian species. | 2001 Jul 6 |
|
| The H3 receptor is involved in cholecystokinin inhibition of food intake in rats. | 2001 Jun 15 |
|
| Histamine H3 receptor-mediated impairment of contextual fear conditioning and in-vivo inhibition of cholinergic transmission in the rat basolateral amygdala. | 2001 Nov |
|
| Histamine H1 receptors mediate the anorectic action of the pancreatic hormone amylin. | 2001 Nov |
|
| Dynamics of histamine H(3) receptor antagonists on brain histamine metabolism: do all histamine H(3) receptor antagonists act at a single site? | 2001 Nov 16 |
|
| Effect of L-carnosine on the hyperglycemia caused by intracranial injection of 2-deoxy-D-glucose in rats. | 2001 Nov 2 |
|
| Regulation of IL-13 production by histamine in cloned murine T helper type 2 cells. | 2001 Oct |
|
| Inhibitory effect of histamine on axonal transport in cultured mouse dorsal root ganglion neurons. | 2001 Oct |
|
| Comparison of human, mouse, rat, and guinea pig histamine H4 receptors reveals substantial pharmacological species variation. | 2001 Oct |
|
| Involvement of central histamine in amygdaloid kindled seizures in rats. | 2001 Oct 15 |
|
| Histamine H(3)-receptor antagonism improves memory retention and reverses the cognitive deficit induced by scopolamine in a two-trial place recognition task. | 2001 Oct 15 |
|
| Histamine H1 receptor-mediated inhibition of potassium-evoked release of 5-hydroxytryptamine from mouse forebrains. | 2001 Oct 15 |
|
| Regional differences in functional receptor distribution and calcium mobilization in the intact human lens. | 2001 Sep |
|
| Muscarinic, adenosine A(2) and histamine H(3) receptor modulation of haloperidol-induced c-fos expression in the striatum and nucleus accumbens. | 2002 |
|
| Contractile response of horse deep dorsal penile vein to histamine. | 2002 Apr |
|
| Histamine H3-receptor blockade in the rat nucleus basalis magnocellularis improves place recognition memory. | 2002 Jan |
|
| Presynaptic H3 autoreceptors modulate histamine synthesis through cAMP pathway. | 2002 Jan |
|
| Histamine regulation of interleukin-18-initiating cytokine cascade is associated with down-regulation of intercellular adhesion molecule-1 expression in human peripheral blood mononuclear cells. | 2002 Jan |
|
| Mouse light/dark box test reveals anxiogenic-like effects by activation of histamine H1 receptors. | 2002 Jan-Feb |
|
| Different role of the histamine H3-receptor in vagal-, betanechol-, pentagastrin-induced gastric acid secretion in anaesthetized rats. | 2002 Jul |
|
| Rodent antinociception following acute treatment with different histamine receptor agonists and antagonists. | 2002 Jun |
|
| Differential in vivo effects of H3 receptor ligands in a new mouse dipsogenia model. | 2002 Jun |
|
| Modulation of the discriminative stimulus effects of cocaine and methamphetamine by the histaminergic system. | 2002 Jun |
|
| Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding. | 2002 Jun |
|
| Role of histamine H3 receptors in control of mouse intestinal motility in vivo and in vitro: comparison with alpha2-adrenoceptors. | 2002 May |
|
| Experimental anxiety induced by histaminergics in mast cell-deficient and congenitally normal mice. | 2002 May |
|
| Influence of SKF 91488, histamine N-methyltransferase inhibitor, on the central cardiovascular regulation during controlled, stepwise hemorrhagic hypotension in rats. | 2002 May-Jun |
|
| Endogenous central histamine-induced reversal of critical haemorrhagic hypotension in rats--studies with histamine N-methyltransferase inhibitor SKF 91488. | 2002 Nov |
|
| Coordination of histamine H3 receptor antagonists with human adrenal cytochrome P450 enzymes. | 2002 Nov |
|
| High-frequency oscillation in the hippocampus of the behaving rat and its modulation by the histaminergic system. | 2003 |
|
| Role of histamine receptors in the regulation of edema and circulation postburn. | 2003 Dec |
|
| Histamine inhibits lipopolysaccharide-induced tumor necrosis factor-alpha production in an intercellular adhesion molecule-1- and B7.1-dependent manner. | 2003 Feb |
|
| Neuroimmune interactions in guinea pig stomach and small intestine. | 2003 Jan |
|
| Central endogenous histamine modulates sympathetic outflow through H3 receptors in the conscious rabbit. | 2003 Jul |
|
| Histamine H4 receptor mediates chemotaxis and calcium mobilization of mast cells. | 2003 Jun |
|
| Two novel and selective nonimidazole H3 receptor antagonists A-304121 and A-317920: II. In vivo behavioral and neurophysiological characterization. | 2003 Jun |
|
| Activation of spinal histamine H3 receptors inhibits mechanical nociception. | 2003 Jun 6 |
|
| Regulation by prostaglandin E2 and histamine of angiogenesis in inflammatory granulation tissue. | 2003 May |
|
| Histamine induces cytoskeletal changes in human eosinophils via the H(4) receptor. | 2003 Nov |
|
| Aminergic control of high-frequency (approximately 200 Hz) network oscillations in the hippocampus of the behaving rat. | 2003 Sep 11 |
|
| Pruritus-associated response mediated by cutaneous histamine H3 receptors. | 2004 Mar |
|
| Involvement of histamine H4 and H1 receptors in scratching induced by histamine receptor agonists in Balb C mice. | 2004 May |
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
Sat Dec 17 03:11:30 UTC 2022
by
admin
on
Sat Dec 17 03:11:30 UTC 2022
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| Record UNII |
II4319BWUI
|
| 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
Created by
admin on Sat Dec 17 03:11:30 UTC 2022 , Edited by admin on Sat Dec 17 03:11:30 UTC 2022
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