522-24-7

Basic information

• Product Name: fenethazine
• Synonyms: fenethazine;Abbott-2780;Anergen;Ethysine;Etisine;Lisergan;SC-1627;dimethyl(2-phenothiazin-10-ylethyl)amine
• CAS NO: 522-24-7
• Molecular Formula: C₁₆H₁₈N₂S
• Molecular Weight: 270.398
• EINECS: 208-325-1
• Mol File: 522-24-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: bp1 183-187°
• Flash Point: 193.3°C
• Appearance: /
• Density: 1.153g/cm³
• Vapor Pressure: 1.75E-06mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: fenethazine(CAS DataBase Reference)
• NIST Chemistry Reference: fenethazine(522-24-7)
• EPA Substance Registry System: fenethazine(522-24-7)

Safety Data

• Hazardous Substances Data: 522-24-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H18N2S/c1-17(2)11-12-18-13-7-3-5-9-15(13)19-16-10-6-4-8-14(16)18/h3-10H,11-12H2,1-2H3

Upstream product

• 92-84-2 10H-phenothiazine 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 
• 31066-28-1 phenothiazine-10-carboxylic acid-(2-dimethylamino-ethyl ester) 
• 18956-87-1 10H-phenothiazine-10-carbonyl chloride 
• 50-00-0 formaldehyd 
• 50971-79-4 2-(10H-phenothiazin-10-yl)ethan-1-amine 

Downstream Products

• 104295-13-8 2-(3,4-dimethoxyphenyl)-N-methyl-N-(2-phenothiazin-10-ylethyl)ethanamine 
• 311332-89-5 2-(4-methoxyphenyl)-N-methyl-N-(2-phenothiazin-10-ylethyl)ethanamine 

Relevant articles and documents

A convenient procedure for the synthesis of phenothiazine drugs

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A Focused Library of Psychotropic Analogues with Neuroprotective and Neuroregenerative Potential

Overcoming the lack of effective treatments and the continuous clinical trial failures in neurodegenerative drug discovery might require a shift from the prevailing paradigm targeting pathogenesis to the one targeting simultaneously neuroprotection and neuroregeneration. In the studies reported herein, we sought to identify small molecules that might exert neuroprotective and neuroregenerative potential as tools against neurodegenerative diseases. In doing so, we started from the reported neuroprotective/neuroregenerative mechanisms of psychotropic drugs featuring a tricyclic alkylamine scaffold. Thus, we designed a focused-chemical library of 36 entries aimed at exploring the structural requirements for efficient neuroprotective/neuroregenerative cellular activity, without the manifestation of toxicity. To this aim, we developed a synthetic protocol, which overcame the limited applicability of previously reported procedures. Next, we evaluated the synthesized compounds through a phenotypic screening pipeline, based on primary neuronal systems. Phenothiazine 2Bc showed improved neuroregenerative and neuroprotective properties with respect to reference drug desipramine (2Aa). Importantly, we have also shown that 2Bc outperformed currently available drugs in cell models of Alzheimer's and Parkinson's diseases and attenuates microglial activation by reducing iNOS expression.

Cation Radicals of Phenothiazines. Part 4. Electron Transfer Between Aquamanganase(III) and N-Alkylphenothiazines

The kinetics of electron transfer between aquamanganase(III) and N-alkylphenothiazines, giving rise to the corresponding cation radicals, has been investigated in the range 0.20-1.50 mol dm-3 HClO4 at different temperatures.The main reaction path has been assigned to the unhydrolysed species Mn(3+)(aq), and there is a dependence of the rate constants on the corresponding reduction potentials.