2804-16-2

Basic information

• Product Name: N-Desmethyl Trifluoperazine Dihydrochloride
• Synonyms: 10-[3-(1-Piperazinyl)propyl]-2-(trifluoromethyl)-10H-phenothiazine Dihydrochloride;10-[3-(1-Piperazinyl)propyl]-2-(trifluoromethyl)phenothiazine Dihydrochloride;Demethyltrifluoperazine Dihydrochloride;Deshydroxyethyl Fluphenazine Dihydrochloride;N-Desmethyl Trifluoperazine Dihydrochloride;NSC 6;NSC 644575;QSS 5
• CAS NO: 2804-16-2
• Molecular Formula: C₂₀H₂₂F₃N₃S
• Molecular Weight: 466.391869
• Product Categories: Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Sulfur & Selenium Compounds;Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 2804-16-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 123-125°C
• Boiling Point: 511 °C at 760 mmHg
• Flash Point: 262.8 °C
• Appearance: White Powder
• Density: 1.253 g/cm³
• Vapor Pressure: 1.48E-10mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly),
• PKA: 9.21±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: N-Desmethyl Trifluoperazine Dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-Desmethyl Trifluoperazine Dihydrochloride(2804-16-2)
• EPA Substance Registry System: N-Desmethyl Trifluoperazine Dihydrochloride(2804-16-2)

Safety Data

• Hazardous Substances Data: 2804-16-2(Hazardous Substances Data)

Usage

Description

N-Desmethyl Trifluoperazine Dihydrochloride, also known as a metabolite of the antipsychotic drugs Trifluoperazine (TFP) and Fluphenazine, is a white powder with unique chemical properties. It is derived from the metabolism of these antipsychotic medications and holds potential applications in various fields due to its specific characteristics.

Uses

Used in Pharmaceutical Industry:
N-Desmethyl Trifluoperazine Dihydrochloride is used as an active pharmaceutical ingredient (API) for its role in the metabolism of antipsychotic drugs. Its presence in the metabolic pathway of TFP and Fluphenazine contributes to the overall efficacy and safety profile of these medications, making it an essential component in the development and formulation of antipsychotic drug therapies.
Used in Research and Development:
In the field of pharmaceutical research and development, N-Desmethyl Trifluoperazine Dihydrochloride serves as a valuable compound for studying the metabolic pathways and pharmacokinetics of antipsychotic drugs. This understanding can lead to the optimization of drug formulations, improved drug delivery systems, and the development of novel therapeutic agents with enhanced efficacy and reduced side effects.
Used in Quality Control and Analysis:
N-Desmethyl Trifluoperazine Dihydrochloride is utilized as a reference standard in the quality control and analysis of antipsychotic drug products. Its chemical properties and white powder form make it suitable for use in high-performance liquid chromatography (HPLC), mass spectrometry, and other analytical techniques to ensure the purity, potency, and consistency of these medications.
Used in Drug Metabolism Studies:
As a metabolite of Trifluoperazine and Fluphenazine, N-Desmethyl Trifluoperazine Dihydrochloride is employed in drug metabolism studies to investigate the biotransformation processes and enzyme interactions involved in the metabolism of these antipsychotic agents. This information is crucial for understanding the pharmacological effects, potential drug-drug interactions, and the development of personalized treatment strategies for patients receiving these medications.

InChI:InChI=1/C20H22F3N3S/c21-20(22,23)15-6-7-19-17(14-15)26(16-4-1-2-5-18(16)27-19)11-3-10-25-12-8-24-9-13-25/h1-2,4-7,14,24H,3,8-13H2

Upstream product

• 110-85-0 piperazine 
• 1675-46-3 10-(3-chloropropyl)-2-trifluoromethylphenothiazine 
• 92-30-8 2-(trifluoromethyl)-10H-phenothiazine 
• 66927-43-3 1-formyl-4-(3-chloropropyl)piperazine 
• 1009797-48-1 tert-butyl 4-(3-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)propyl)piperazine-1-carboxylate 
• 440-17-5 trifluoperazine dihydrochloride 

Downstream Products

• 2021-89-8 4-<3-(2-Trifluormethyl-phenothiazinyl-(10))-propyl>-piperazin-ethylacetat-(1) 
• 83016-35-7 fluphenazine-N-mustard 
• 2839-69-2 4-(2-{4-[3-(2-trifluoromethyl-phenothiazin-10-yl)-propyl]-piperazin-1-yl}-ethyl)-aniline 
• 3831-67-2 4-{4-[3-(2-trifluoromethyl-phenothiazin-10-yl)-propyl]-piperazin-1-ylmethyl}-aniline 
• 140868-63-9 ({[((S)-1-[3-(2,4-Dinitro-phenyl)-3H-imidazol-4-ylmethyl]-2-oxo-2-{4-[3-(2-trifluoromethyl-phenothiazin-10-yl)-propyl]-piperazin-1-yl}-ethylcarbamoyl)-methyl]-carbamoyl}-methyl)-carbamic acid tert-butyl ester 
• 140868-62-8 (S)-2-Amino-3-[3-(2,4-dinitro-phenyl)-3H-imidazol-4-yl]-1-{4-[3-(2-trifluoromethyl-phenothiazin-10-yl)-propyl]-piperazin-1-yl}-propan-1-one 
• 140868-61-7 ((S)-1-[3-(2,4-Dinitro-phenyl)-3H-imidazol-4-ylmethyl]-2-oxo-2-{4-[3-(2-trifluoromethyl-phenothiazin-10-yl)-propyl]-piperazin-1-yl}-ethyl)-carbamic acid tert-butyl ester 
• 3871-14-5 1-[(4-amino-phenyl)-acetyl]-4-[3-(2-trifluoromethyl-phenothiazin-10-yl)-propyl]-piperazine 
• 3826-39-9 1-phenylacetyl-4-[3-(2-trifluoromethyl-phenothiazin-10-yl)-propyl]-piperazine 
• 2793-61-5 1-benzoyl-4-[3-(2-trifluoromethyl-phenothiazin-10-yl)-propyl]-piperazine 
• 3862-89-3 10-{3-[4-(4-nitro-benzyl)-piperazin-1-yl]-propyl}-2-trifluoromethyl-10H-phenothiazine 
• 16498-21-8 10-{3-[4-(2-[1,3]dioxan-2-yl-ethyl)-piperazin-1-yl]-propyl}-2-trifluoromethyl-10H-phenothiazine 
• 69-23-8 Fluphenazine 

Relevant articles and documents

Phenothiazine compound and application thereof

The invention provides a phenothiazine compound and application thereof to preparation of drugs for curing breast cancer and melanoma. The phenothiazine compound has higher inhibitory activity on thebreast cancer cell MDA- MB- 231, SUM159, MCF- 7, SKBR- 3 and the melanoma cell A375 and B16BL6 than trifluoperazine and thioridazine, and can be applied to curing breast cancer and melanoma. The general formula of the phenothiazine compound is as following (the formula is shown in the description), wherein R1 and R2 are as shown in the description.

Repositioning of the antipsychotic trifluoperazine: Synthesis, biological evaluation and in silico study of trifluoperazine analogs as anti-glioblastoma agents

Repositioning of the antipsychotic drug trifluoperazine for treatment of glioblastoma, an aggressive brain tumor, has been previously suggested. However, trifluoperazine did not increase the survival time in mice models of glioblastoma. In attempt to identify an effective trifluoperazine analog, fourteen compounds have been synthesized and biologically in vitro and in vivo assessed. Using MTT assay, compounds 3dc and 3dd elicited 4–5 times more potent inhibitory activity than trifluoperazine with IC50 = 2.3 and 2.2 μM against U87MG glioblastoma cells, as well as, IC50 = 2.2 and 2.1 μM against GBL28 human glioblastoma patient derived primary cells, respectively. Furthermore, they have shown a reasonable selectivity for glioblastoma cells over NSC normal neural cell. In vivo evaluation of analog 3dc confirmed its advantageous effect on reduction of tumor size and increasing the survival time in brain xenograft mouse model of glioblastoma. Molecular modeling simulation provided a reasonable explanation for the observed variation in the capability of the synthesized analogs to increase the intracellular Ca2+ levels. In summary, this study presents compound 3dc as a proposed new tool for the adjuvant chemotherapy of glioblastoma.

NOVEL COMPOSITIONS AND METHODS FOR TREATMENT OF DISEASES RELATED TO ACTIVATED LYMPHOCYTES

The present invention relates to inhibiting proliferation and inducing apoptosis in activated lymphocytes, including T cells and B cells. The invention also provides compositions and methods for inhibiting proliferation and inducing apoptosis in activated lymphocytes, as well methods for treating diseases associated with activated lymphocytes by administering 5-HT receptor antagonists.