Thioperamide

Names

[ Name ]:
Thioperamide

[Synonym ]:
Thioperamide
Tocris-0644
1-Piperidinecarbothioamide, N-cyclohexyl-4-(1H-imidazol-5-yl)-, (2Z)-2-butenedioate (1:1)
N-Cyclohexyl-4-(1H-imidazol-5-yl)-1-piperidinecarbothioamide (2Z)-2-butenedioate (1:1)
1-Piperidinecarbothioamide, N-cyclohexyl-4-(1H-imidazol-4-yl)-, (2Z)-2-butenedioate (1:1)
Lopac-T-123
N-Cyclohexyl-4-(1H-imidazol-4-yl)piperidine-1-carbothioamide (2Z)-but-2-enedioate (1:1)
thioperamine

Biological Activity

[Description]:

Thioperamide (MR-12842) is a potent, orally available, brain penetrant and selective H3 receptor antagonist with a Ki of 4.3 nM for inhibition of [3H]histamine release. Thioperamide inhibits [3H]histamine synthesis with a Ki of 31 nM[1].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> Histamine Receptor

[Target]

H3 Receptor

[In Vitro]

Thioperamide inhibits [3H]-(R)α-MeHA binding rat brain and guinea-pig lung with Kis of 2.1 nM and 2.0 nM, respectively. Thioperamide competitively blocks H3-autoreceptors regulating [3H]histamine release with a mean apparent Ki of 4 nM[1]. Thioperamide (0.01-100 μM; 24 hours) promotes the viability of NE-4C stem cells in a concentration-dependent manner[2]. Cell Viability Assay[2] Cell Line: NE-4C stem cells Concentration: 0.01, 0.1, 1, 10, 100 μM Incubation Time: 24 hours Result: The viability of NE-4C stem cells increased significantly to 150.83±6.91% when (1 μM) was administrated, and increased to 145.11±14.52% and 132.02%±25.65% when 10 μM and 100 μM were administrated respectively.

[In Vivo]

Thioperamide (5-20 mg/kg; i.p.) is able to facilitate reconsolidation of a contextually-conditioned fear memory in C57BL/6J mice[3]. Animal Model: Naive female C57BL/6J mice[3] Dosage: 5, 10 or 20 mg/kg Administration: Injections (i.p.) Result: Facilitated reconsolidation of a contextually-conditioned fear memory.

[References]

[1]. J M Arrang, et al. Highly Potent and Selective Ligands for Histamine H3-receptors. Nature. 1987 May 14-20;327(6118):117-23.

[2]. Na Wang, et al. Histamine H3 Receptor Antagonist Enhances Neurogenesis and Improves Chronic Cerebral Hypoperfusion-Induced Cognitive Impairments. Front Pharmacol. 2020 Jan 21;10:1583.

[3]. Y Charlier, et al. Differential Effects of Histamine H(3) Receptor Inverse Agonist Thioperamide, Given Alone or in Combination With the N-methyl-d-aspartate Receptor Antagonist Dizocilpine, on Reconsolidation and Consolidation of a Contextual Fear Memory in Mice. Neuroscience. 2011 Oct 13;193:132-42.

Chemical & Physical Properties

[ Density]:
1.2 g/cm3

[ Boiling Point ]:
499.5ºC at 760 mmHg

[ Molecular Formula ]:
C₁₅H₂₄N₄S

[ Molecular Weight ]:
408.515

[ Flash Point ]:
255.9ºC

[ Exact Mass ]:
408.183136

[ PSA ]:
150.64000

[ LogP ]:
2.83690

[ Vapour Pressure ]:
4.12E-10mmHg at 25°C

[ Index of Refraction ]:
1.614

Safety Information

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%