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1.a compound used primarily in veterinary medicine to rid farm animals of internal parasites
|Jmol-3D images||Image 1|
|Molar mass||199.27 g/mol|
|Appearance||yellow rhombic leaflets or
185 °C, 458 K, 365 °F
371 °C, 644 K, 700 °F
|Solubility in water||0.00051 g/L (20 °C)|
|Solubility in other solvents||benzene, ether, petroleum ether, chloroform, hot acetic acid, ethanol (slightly), mineral oil (slightly)|
|Acidity (pKa)||approx 23 in DMSO|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Phenothiazine is an organic compound that occurs in various antipsychotic and antihistaminic drugs. It has the formula S(C6H4)2NH. This yellow tricyclic compound is soluble in acetic acid, benzene, and ether. The compound is related to the thiazine-class of heterocyclic compounds. Derivatives of the parent compound find wide use as drugs.
The compound was originally prepared by Bernthsen in 1883 via the reaction of diphenylamine with sulfur, but more recent syntheses rely on the cyclization of 2-substituted diphenylsulfide. The pharmaceutically significant derivatives of phenothiazine are not prepared from phenothiazine.
The synthetic dye methylene blue, containing the structure, was described in 1876. Phenothiazine itself was introduced by DuPont as an insecticide in 1935. It is sometimes used as an antihelminthic in livestock.
Many water soluble phenothiazine derivatives such as methylene blue, methylene green, thionine, and others are able to be electropolymerized into conductive polymers that are used as electrocatalysts for NADH oxidation in enzymatic biosensors and biofuel cells. ,,
The phenothiazine structure occurs in various neuroleptic drugs, e.g. chlorpromazine, and antihistaminic drugs, e.g. promethazine. The term "phenothiazines" describes the largest of the five main classes of neuroleptic antipsychotic drugs. These drugs have antipsychotic and, often, antiemetic properties, although they may also cause severe side effects such as extrapyramidal symptoms (including akathisia and tardive dyskinesia), hyperprolactinaemia, and the rare but potentially fatal neuroleptic malignant syndrome as well as substantial weight gain.
Phenothiazine antipsychotics are classified into three groups that differ with respect to the substituent on nitrogen: the aliphatic compounds (bearing acyclic groups), the "piperidines" (bearing piperidine-derived groups), and the piperazine (bearing piperazine-derived substituents).
|moderate||Chlorpromazine (marketed as Thorazine, Chlor-PZ, Klorazine, Promachlor, Promapar, Sonazine, Chlorprom, Chlor-Promanyl, Largactil)||strong||moderate|
|Promazine (trade name Sparine)||moderate||moderate|
|Triflupromazine (trade names Clinazine, Novaflurazine, Pentazine, Terfluzine, Triflurin, Vesprin)||strong||moderate/strong|
|Levomepromazine in Germany and Methotrimeprazine in America (trade names Nozinan, Levoprome)||extremely strong||low|
|Piperidines||strong||Mesoridazine (trade name Serentil)||strong||weak|
|Thioridazine (trade names Mellaril, Novoridazine, Thioril)||strong||weak|
|Piperazines||weak||Fluphenazine (trade names Prolixin, Permitil, Modecate, Moditen)||weak/moderate||strong|
|Perphenazine (sold as Trilafon, Etrafon, Triavil, Phenazine)||weak/moderate||strong|
|Prochlorperazine (trade names Compazine, Stemetil)|
|Trifluoperazine (trade name Stelazine)||moderate||strong|
Like many commercially significant compounds, phenothiazine has numerous trade names including AFI-Tiazin; Agrazine; Antiverm; Biverm; Dibenzothiazine; Orimon; Lethelmin; Souframine; Nemazene; Vermitin; Padophene; Fenoverm; Fentiazine; Contaverm; Fenothiazine; Phenovarm; Ieeno; ENT 38; Helmetina; Helmetine, Penthazine; XL-50; Wurm-thional; Phenegic; Phenovis; Phenoxur; Reconox.