T8516

Trifluoperazine dihydrochloride

≥99%, powder

• 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/REAXYS Number: 3820024
• EC Number: 207-123-0
• MDL number: MFCD00012656
• UNSPSC Code: 12352200
• PubChem Substance ID: 57654709
• NACRES: NA.77

Properties

• 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)

Description

Application

Trifluoperazine dihydrochloride has been used as a calmodulin kinase antagonist in cultured Aplysia californica neurons[1]. Trifluoperazine dihydrochloride has also been used as a PMCA inhibitor in mouse duodenal tissues to block the transcellular active calcium flux[2].

Trifluoperazine dihydrochloride has been used:

• to inhibit clathrin-dependent endocytosis[3]
• as a calmodulin kinase antagonist in cultured Aplysia californica neurons[1]
• as a plasma membrane Ca²⁺-ATPase (PMCA) inhibitor in mouse duodenal tissues to block the transcellular active calcium flux[2]

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.[4]

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).

Safety Information

• pictograms: GHS08,GHS07,GHS09
• signalword: Danger
• hcodes: H302,H319,H336,H341,H372,H410
• pcodes: P201 - P273 - P301 + P312 + P330 - P305 + P351 + P338 - P308 + P313
• 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_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves