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T9025

Sigma-Aldrich

Thioridazine hydrochloride

≥99%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C21H26N2S2 · HCl
CAS Number:
130-61-0
Molecular Weight:
407.04
EC Number:
204-992-8
MDL number:
MFCD00012655
UNSPSC Code:
12352200
PubChem Substance ID:
57654711
NACRES:
NA.77

assay

≥99%

solubility

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

SMILES string

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

InChI key

NZFNXWQNBYZDAQ-UHFFFAOYSA-N

Gene Information

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.

Biochem/physiol Actions

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

Preparation Note

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
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
Allison L Boyd et al.
Cancer cell, 34(3), 483-498 (2018-09-12)
Despite successful remission induction, recurrence of acute myeloid leukemia (AML) remains a clinical obstacle thought to be caused by the retention of dormant leukemic stem cells (LSCs). Using chemotherapy-treated AML xenografts and patient samples, we have modeled patient remission and
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