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T8516

Sigma-Aldrich

Trifluoperazine dihydrochloride

≥99%, powder

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Synonym(s):
10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride
Empirical Formula (Hill Notation):
C21H24F3N3S · 2HCl
CAS Number:
440-17-5
Molecular Weight:
480.42
Beilstein:
3820024
EC Number:
207-123-0
MDL number:
MFCD00012656
UNSPSC Code:
12352200
PubChem Substance ID:
57654709
NACRES:
NA.77

Quality Level

100

Assay

≥99%

form

powder

color

white to off-white

mp

243 °C (dec.) (lit.)

solubility

ethanol: soluble 5 mg/mL
H2O: soluble 50 mg/mL, clear, colorless to yellow
DMSO: soluble

storage temp.

−20°C

SMILES string

Cl[H].Cl[H].CN1CCN(CCCN2c3ccccc3Sc4ccc(cc24)C(F)(F)F)CC1

InChI

1S/C21H24F3N3S.2ClH/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24;;/h2-3,5-8,15H,4,9-14H2,1H3;2*1H

InChI key

BXDAOUXDMHXPDI-UHFFFAOYSA-N

Gene Information

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

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Application

Trifluoperazine dihydrochloride has been used as a calmodulin kinase antagonist in cultured Aplysia californica neurons. Trifluoperazine dihydrochloride has also been used as a PMCA inhibitor in mouse duodenal tissues to block the transcellular active calcium flux.
Trifluoperazine dihydrochloride has been used:
  • to inhibit clathrin-dependent endocytosis
  • as a calmodulin kinase antagonist in cultured Aplysia californica neurons
  • as a plasma membrane Ca2+-ATPase (PMCA) inhibitor in mouse duodenal tissues to block the transcellular active calcium flux

Biochem/physiol Actions

Phenothiazine antipsychotic; D2 dopamine receptor antagonist; inhibits calmodulin-dependent stimulation of 3′:5′-cyclic nucleotide phosphodiesterase; inhibits cAMP-gated cation channels.
Trifluoperazine dihydrochloride is useful in treating schizophrenia, disturbed behavior, severe anxiety, nausea and vomiting.

Features and Benefits

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

Preparation Note

Trifluoperazine dihydrochloride dissolves in water at 50 mg/ml, with heat as required, and yields a clear, colorless to yellow solution. It is also soluble in DMSO and ethanol (5 mg/ml).

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Muta. 2 - STOT RE 1 - STOT SE 3

Target Organs

Central nervous system, Eyes

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)

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M Carballo et al.
The Journal of biological chemistry, 274(1), 93-100 (1998-12-29)
We describe here a specific calcineurin activity in neutrophil lysates, which is dependent on Ca2+, inhibited by trifluoroperazine, and insensitive to okadaic acid. Immunoblotting experiments using a specific antiserum recognized both the A and B chains of calcineurin. Neutrophils treated
E C Samouilidou et al.
Life sciences, 62(1), 29-36 (1998-01-28)
This study was designed to examine the role of calcium in the ischemia-induced changes of calmodulin-stimulated Ca2+-ATPase activity of heart sarcolemma of dogs subjected to coronary artery ligation (90 min) and reperfusion (30 min). This was attained by the application
Extractive spectrophotometric determination of chlorpromazine and trifluoperazine hydrochloride in pharmaceutical preparations
Hassouna MEM, et al.
Egyptian Journal of Forensic Sciences, 2(2), 62-68 (2012)
Uptake of polyphosphate microparticles in vitro (SaOS-2 and HUVEC cells) followed by an increase of the intracellular ATP pool size
Muller WEG, et al.
PLoS ONE, 12(12), e0188977-e0188977 (2017)
R L Mach et al.
Biochimica et biophysica acta, 1403(3), 281-289 (1998-08-01)
The addition of Ca2+-antagonizers (La2+), Ca2+-ionophores (A23187) and Ca2+-complexing agents (EGTA) inhibited the formation of xylanase activity in resting mycelia of Trichoderma reesei. The inhibition by the ionophore was reversed by the addition of Ca2+ ions. A similar inhibitory effect
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