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Sigma-Aldrich

Thioperamide maleate salt

solid

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Synonym(s):
MR-12842, N-Cyclohexyl-4-(1H-imidazol-4-yl)-1-piperidinecarbothioamide maleate salt
Empirical Formula (Hill Notation):
C15H24N4S · C4H4O4
CAS Number:
148440-81-7
Molecular Weight:
408.52
MDL number:
MFCD00083209
UNSPSC Code:
12352200
PubChem Substance ID:
24277809
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated
under inert gas

color

white

solubility

H2O: >10 mg/mL
DMSO: 12 mg/mL
ethanol: 3 mg/mL

SMILES string

OC(=O)\C=C/C(O)=O.S=C(CC1CCCCC1)N2CCC(CC2)c3c[nH]cn3

InChI

1S/C16H25N3S.C4H4O4/c20-16(10-13-4-2-1-3-5-13)19-8-6-14(7-9-19)15-11-17-12-18-15;5-3(6)1-2-4(7)8/h11-14H,1-10H2,(H,17,18);1-2H,(H,5,6)(H,7,8)/b;2-1-

InChI key

REZRBLGMJZZSID-BTJKTKAUSA-N

Gene Information

human ... HRH3(11255)

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Application

Thioperamide maleate salt was used to study the sympathetic and autonomic nerve activity in mammalian white adipose tissue.

Biochem/physiol Actions

Potent and selective H3 histamine receptor antagonist that crosses the blood-brain barrier.
Thioperamide is a potent and selective H3 histamine receptor antagonist that crosses the blood-brain barrier. It affects the central histaminergic system and decreases the duration of seizures and convulsions in mice. It also improves learning deficit induced by other drugs such as scopolamine.

Features and Benefits

This compound is featured on the Histamine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S Miyazaki et al.
Life sciences, 57(23), 2137-2144 (1995-01-01)
We examined the effects of thioperamide and (R)-alpha-methylhistamine, a histamine H3-receptor antagonist and an agonist, respectively, on a scopolamine-induced learning deficit using an elevated plus-maze test in mice. Thioperamide alone slightly improved the learning deficit induced by scopolamine, and pretreatment
Jiao Shen et al.
Neuroscience letters, 441(1), 100-104 (2008-07-05)
Previously, we showed that l-carnosine, a bioactive dipeptide, influences the sympathetic nerve activity innervating kidney and brown adipose tissue. Because the autonomic nervous system plays an important role in the regulation of lipid metabolism, we investigated the in vivo effects
Jiao Shen et al.
Neuroscience letters, 444(2), 166-171 (2008-08-30)
Previously, we showed that orexin-A, a 33-aa peptide, influences renal sympathetic nerve activity. Because the autonomic nervous system plays an important role in the regulation of lipid metabolism, we investigated the in vivo effects of orexin-A on the sympathetic nerve
H Yokoyama et al.
European journal of pharmacology, 234(1), 129-133 (1993-03-30)
The effect of thioperamide, a histamine H3 receptor antagonist, on electrically induced convulsions was studied in mice. Thioperamide significantly and dose dependently decreased the duration of each phase of convulsion and raised the electroconvulsive threshold. Its anticonvulsant effects were prevented
Toshiaki Matsutomo et al.
Journal of pharmaceutical and biomedical analysis, 168, 148-154 (2019-02-27)
Our previous study has shown that a single dose of S-1-propenylcysteine (S1PC) exerted an antihypertensive effect in spontaneously hypertensive rats (SHR), while its mode of action remained to be further investigated. The aim of this study was to explore the
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