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Merck

T8516

Trifluoperazine dihydrochloride

≥99%, D2 dopamine receptor antagonist, powder

Sinónimos:

10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride

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About This Item

Fórmula empírica (notación de Hill):
C21H24F3N3S · 2HCl
Número CAS:
440-17-5
Peso molecular:
480.42
NACRES:
NA.77
PubChem Substance ID:
57654709
UNSPSC Code:
12352200
EC Number:
207-123-0
MDL number:
MFCD00012656
Beilstein/REAXYS Number:
3820024

Nombre del producto

Trifluoperazine dihydrochloride, ≥99%, powder

InChI key

BXDAOUXDMHXPDI-UHFFFAOYSA-N

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

SMILES string

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

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

Quality Level

100

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).

signalword

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

Clase de almacenamiento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
WXBF0268V
WXBF1783V
WXBD8259V
WXBD2895V
MKCM9312

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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
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)
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
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)
Elizabeth Terry-Kantor et al.
International journal of molecular sciences, 21(15) (2020-07-28)
Genetic and biochemical evidence attributes neuronal loss in Parkinson's disease (PD) and related brain diseases to dyshomeostasis of the 14 kDa protein α-synuclein (αS). There is no consensus on how αS exerts toxicity. Explanations range from disturbed vesicle biology to
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