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T123

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
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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1 of 4

This Item
R134M137L109
Thioperamide maleate salt solid

Sigma-Aldrich

T123

Thioperamide maleate salt

Rilmenidine hemifumarate salt solid

Sigma-Aldrich

R134

Rilmenidine hemifumarate salt

Methysergide maleate salt solid

Sigma-Aldrich

M137

Methysergide maleate salt

Lorglumide sodium salt solid

Sigma-Aldrich

L109

Lorglumide sodium salt

form

solid

form

solid

form

solid

form

solid

storage condition

desiccated, under inert gas

storage condition

-

storage condition

-

storage condition

-

color

white

color

white

color

white to off-white

color

white

solubility

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

solubility

DMSO: >10 mg/mL, H2O: insoluble

solubility

DMSO: >10 mg/mL, H2O: 2 mg/mL

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: >10 mg/mL, H2O: 10 mg/mL, methanol: 28 mg/mL

Gene Information

human ... HRH3(11255)

Gene Information

human ... NISCH(11188)

Gene Information

human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR7(3363)

Gene Information

human ... CCKAR(886)

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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
M Garbarg et al.
European journal of pharmacology, 164(1), 1-11 (1989-05-02)
The interaction of the potent histamine H3-receptor ligands i.e. (R)alpha-methylhistamine, an agonist, and thioperamide, an antagonist, with the three classes of cerebral histamine receptors was studied in vitro and in vivo. The histamine-induced stimulation of 3',5'-cyclic AMP accumulation in slices
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