T9025

Thioridazine hydrochloride

Name: Thioridazine hydrochloride
Brand: SIGMA

≥99%, D2 dopamine receptor antagonist

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

NACRES:

NA.77

PubChem Substance ID:

57654711

UNSPSC Code:

12352200

EC Number:

204-992-8

MDL number:

MFCD00012655

Product Name

Thioridazine hydrochloride, ≥99%

InChI key

NZFNXWQNBYZDAQ-UHFFFAOYSA-N

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

SMILES string

Cl.CSc1ccc2Sc3ccccc3N(CCC4CCCCN4C)c2c1

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

Quality Level

100

Gene Information

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

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Bioactive Small Molecules

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

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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The effect of selective serotonin re-uptake inhibitors on cytochrome P4502D6 (CYP2D6) activity in human liver microsomes.

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

Effects of Ca(2+)-ionophore A23187 and calmodulin antagonists on regulatory mechanisms of glycolysis and cell viability of NIH-3T3 fibroblasts.

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

Assessments of Thioridazine as a Helper Compound to Dicloxacillin against Methicillin-Resistant Staphylococcus aureus: In Vivo Trials in a Mouse Peritonitis Model.

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

Evaluation of damage to DNA induced by UV-C radiation and chemical agents using electrochemical biosensor based on low molecular weight DNA and screen-printed carbon electrode.

Hlavata, L., et al.

Electrochimica Acta, 71, 134-139 (2012)

Heat shock proteins 70 and 90 increase calcineurin activity in vitro through calmodulin-dependent and independent mechanisms.

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

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