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Merck
CN

T8516

Trifluoperazine dihydrochloride

≥99%, D2 dopamine receptor antagonist, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C21H24F3N3S · 2HCl
CAS Number:
440-17-5
Molecular Weight:
480.42
NACRES:
NA.77
PubChem Substance ID:
57654709
UNSPSC Code:
12352200
EC Number:
207-123-0
MDL number:
MFCD00012656
Beilstein/REAXYS Number:
3820024
Assay:
≥99%
Form:
powder
Quality level:
100

Key Documents

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Product Name

Trifluoperazine dihydrochloride, ≥99%, powder

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)

Related Categories

Application

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

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.

Biochem/physiol Actions

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

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).

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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

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
WXBF0268V
WXBF1783V
WXBD8259V
WXBD2895V
MKCM9312

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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)
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
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
Anne Y Hung et al.
Journal of neurophysiology, 97(3), 2465-2479 (2007-03-14)
The translation of prior activity into changes in excitability is essential for memory and the initiation of behavior. After brief synaptic input, the bag cell neurons of Aplysia californica undergo a nearly 30-min afterdischarge to release egg-laying hormone. The present
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Global Trade Item Number

SKUGTIN
T8516-10G04061837379314
T8516-5G04061837379321

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