21786-08-3

Basic information

• Product Name: 10-(2-chloroethyl)-10H-phenothiazine
• CAS NO: 21786-08-3
• Molecular Formula: C₁₄H₁₂ClNS
• Molecular Weight: 261.7698
• Mol File: 21786-08-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 396.8°C at 760 mmHg
• Flash Point: 193.8°C
• Density: 1.273g/cm³
• Vapor Pressure: 1.66E-06mmHg at 25°C
• Refractive Index: 1.651
• CAS DataBase Reference: 10-(2-chloroethyl)-10H-phenothiazine(CAS DataBase Reference)
• NIST Chemistry Reference: 10-(2-chloroethyl)-10H-phenothiazine(21786-08-3)
• EPA Substance Registry System: 10-(2-chloroethyl)-10H-phenothiazine(21786-08-3)

Safety Data

• Hazardous Substances Data: 21786-08-3(Hazardous Substances Data)

Usage

Chemical class

Phenothiazine

Use

Antipsychotic medication and tranquilizer

Mechanism of action

Alters the effects of certain chemicals in the brain

Effective treatment for

Schizophrenia and other psychotic disorders

Additional use

Antiemetic to control nausea and vomiting

Context for antiemetic use

Surgery and chemotherapy

Exploratory potential

Anti-tumor and anti-inflammatory properties

Precaution

Careful monitoring by a healthcare professional

Concerns

Potential for adverse side effects and interactions with other medications

Upstream product

• 786-50-5 10-chloroacetylphenothiazine 
• 92-84-2 10H-phenothiazine 
• 80-41-1 2-chloroethyl tosylate 
• 109-72-8 n-butyllithium 

Downstream Products

• 18834-03-2 10-(2-triphenylsilanyl-ethyl)-10H-phenothiazine 
• 60-91-3 diethazine 
• 102240-88-0 10-(2-4'-Ethyl-1'-piperazinylethyl)-phenthiazin 

Relevant articles and documents

An Inhibitor of the Interaction of Survivin with Smac in Mitochondria Promotes Apoptosis

Herein we report the first small molecule that disrupts the survivin-Smac interaction taking place in mitochondria. The inhibitor, PZ-6-QN, was identified by initially screening a phenothiazine library using a fluorescence anisotropy assay and then conducting a structure–activity relationship study. Mutagenesis and molecular docking studies suggest that PZ-6-QN binds to survivin similarly to the known Smac peptide, AVPI. The results of the effort also show that PZ-6-QN exhibits good anticancer activity against various cancer cells. Moreover, cell-based mechanistic studies provide evidence for the proposal that PZ-6-QN enters mitochondria to inhibit the survivin-Smac interaction and promotes release of Smac and cytochrome c from mitochondria into the cytosol, a process that induces apoptosis in cancer cells. Overall, the present study suggests that PZ-6-QN can serve as a novel chemical probe for study of processes associated with the mitochondrial survivin-Smac interaction and it will aid the discovery of novel anticancer agents.

Heterocyclic Free Radicals. Part 10. Phenothiazine Cation-Radicals as Probes of the Inductive Effect

Phenothiazine cation-radicals, functionalised at nitrogen by polymethylene chains which terminate in polar substituents, exhibit nitrogen hyperfine splittings which vary regularly with the length of the polymethylene chain and with the polarity of the terminal substituent, as measured by ?1.The cation-radicals are thus probes of the inductive effect which give quantitative insight into its transmisson mechanisms and its attenuation by intervening bonds.For chain-lengths longer than a single methylene group, the field effects of the polar terminal substituents are correlated by a cosθ/r3 function which implies that any terminal substituent may be modelled as a point-dipole whose mean orientation and mean separation from the radical aminium centre are determined by the conformational preferences of the polymethylene chain.Literature values of ?1 for certain substituents are questioned in the light of the results obtained and inductive substituent constants, in general, are discussed.