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T9025

Sigma-Aldrich

Thioridazine hydrochloride

≥99%

Synonyme(s) :

10-[2-(1-Methyl-2-piperidyl)ethyl]-2-(methylthio)-10H-phenothiazine hydrochloride

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About This Item

Formule empirique (notation de Hill):
C21H26N2S2 · HCl
Numéro CAS:
130-61-0
Poids moléculaire :
407.04
Numéro CE :
204-992-8
Numéro MDL:
MFCD00012655
Code UNSPSC :
12352200
ID de substance PubChem :
57654711
Nomenclature NACRES :
NA.77

Pureté

≥99%

Solubilité

H2O: soluble 250 mg plus 5 ml of solvent, clear, colorless to faintly yellow
chloroform: soluble
diethyl ether: insoluble
ethanol: soluble
methanol: soluble

Chaîne SMILES 

Cl.CSc1ccc2Sc3ccccc3N(CCC4CCCCN4C)c2c1

InChI

1S/C21H26N2S2.ClH/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(24-2)15-19(21)23;/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3;1H

Clé InChI

NZFNXWQNBYZDAQ-UHFFFAOYSA-N

Informations sur le gène

human ... DRD2(1813) , DRD3(1814) , DRD4(1815) , HTR2A(3356) , HTR2C(3358)

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Application

Thioridazine hydrochloride has been used as an intercalating agent for analyzing the integrity of double-stranded DNA (dsDNA) using square-wave voltammetry (SWV) techniques. Thioridazine hydrochloride has also been used as a positive control for the inhibition of hepatic enzyme cytochrome P4502D6 (CYP2D6) in human liver microsomes.

Actions biochimiques/physiologiques

D2 dopamine receptor antagonist; phenothazine antipsychotic with reduced extrapyramidal side effects; Ca2+ channel blocker.

Notes préparatoires

250 mg of thioridazine hydrochloride is soluble in 5 ml of water and yields a clear, colorless to faint yellow solution. Thioridazine hydrochloride is also soluble in methanol, ethanol, and chloroform, but it is insoluble in ether.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Michael Stenger et al.
PloS one, 10(8), e0135571-e0135571 (2015-08-13)
The rise in antimicrobial resistance is a major global concern and requires new treatment strategies. The use of helper compounds, such as thioridazine (TDZ), an antipsychotic drug, in combination with traditional antibiotics must be investigated. The aim of this study
J S Someren et al.
Biochemical and biophysical research communications, 260(3), 619-625 (1999-07-15)
We have shown that heat shock proteins (HSPs) associated with steroid receptor complexes are involved in the activation of calcineurin by aldosterone and dexamethasone. To determine whether HSPs directly interact with calcineurin, we measured the effect of HSPs 90, 70
J G Shin et al.
Drug metabolism and disposition: the biological fate of chemicals, 27(9), 1078-1084 (1999-08-26)
The ability of antipsychotic drugs to inhibit the catalytic activity of five cytochrome P-450 (CYP) isoforms was compared using in vitro human liver microsomal preparations to evaluate the relative potential of these drugs to inhibit drug metabolism. The apparent kinetic
H K Crewe et al.
British journal of clinical pharmacology, 34(3), 262-265 (1992-09-01)
Inhibition of human cytochrome P4502D6 (CYP2D6)-catalysed metabolism can lead to clinically significant alterations in pharmacokinetics. Since there is evidence that the selective serotonin reuptake inhibitor (SSRI) class of antidepressant drugs might inhibit CYP2D6, the effects of five SSRIs on human
M Ashkenazy-Shahar et al.
Molecular genetics and metabolism, 67(4), 334-342 (1999-08-13)
We studied here, in NIH-3T3 fibroblasts, the effect of the Ca(2+)-ionophore A23187 (which is known to increase intracellular-free Ca(2+)) on the control of glycolysis and cell viability and the action of calmodulin antagonists. Time-response studies with Ca(2+)-ionophore A23187 have revealed
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