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20-September-2008 09:55:57 - Phenothiazine Phenothiazine Phenothiazine Phenothiazine3D IUPAC name 10H-phenothiazine Other names thiodiphenylamine, dibenzothiazine Identifiers CAS number 92-84-2 Properties Molecular formula C12H9NS Molar mass 199.2762 g/mol Appearance yellow rhombic leaflets or diamond-shaped plates Density ? g/cm3, solid at STP Melting point 185 °C Boiling point 371 °C Solubility in other solvents water, petroleum ether, chloroform Acidity pKa approx 23 in DMSO Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Phenothiazine, also called dibenzothiazine or thiodiphenylamine is a yellow compound soluble in hot acetic acid, benzene, and ether. It is a three-ring structure compound in which two benzene rings are joined by a sulfur and nitrogen atom at nonadjacent positions. It is obtained by fusing diphenylamine with sulfur. It is a dibenzo derivative of thiazine, although thiazine itself is not used as a starting point in the manufacturing of this molecule. It is a semi-volatile organic compound and environmental toxicant of concern to the United States Environmental Protection Agency.1 Contents 1 Overview 2 Synonyms for the chemical phenothiazine 3 Phenothiazine-derivative drugs 4 References 5 Further reading Overview The phenothiazine structure occurs in various neuroleptic drugs, e.g. Chlorpromazine, and antihistaminic drugs, e.g. Promethazine. The synthetic dye methylene blue, containing the structure, was invented in 1876. Phenothiazine itself was introduced by DuPont as an insecticide in 1935.2 It is sometimes used as an antihelminthic in livestock. Synonyms for the chemical phenothiazine Dibenzoparathiazine; Thiodiphenylamine; 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. 3 Phenothiazine-derivative drugs The term phenothiazines is used to describe 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 akathisia, tardive dyskinesia, extrapyramidal symptoms, and the rare but potentially fatal neuroleptic malignant syndrome as well as substantial weight gain. Phenothiazines are used as inodilators in congestive heart failure, acting upon the type I calcium/calmodulin dependent phosphodiesterase.4 There are three groups of phenothiazine antipsychotics, differing by their chemical structure and their pharmacological effects. They are the aliphatic compounds, the piperidines and piperazines. Group Autonomic Example Sedative Extrapyramidal side-effect Aliphatic compounds 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 Stelazine, 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 Flupentixol sold as Depixol, Fluanxol moderate strong Prochlorperazine trade names Compazine, Stemetil Trifluoperazine trade name Stelazine moderate strong References ^ Five-Year Review Report Forest Glen Mobile Home Subdivision Site City of Niagara Falls and Town of Niagara Niagara County, New York Prepared by U.S. Environmental Protection Agency September 2002 ^ History of Insecticides and Control Equipment Clemson University Pesticide Information Program. ^ U.S. Department of Labor Occupational Safety Health Administration Chemical Sampling Information Phenothiazine Also see: OSHA Also see:PAN Pesticides Database ^ Rang; Dale et al, Pharmacology, 6th ion Further reading Hendricks, Christensen, J.B., and Kristiansen, Jette E. Sonderborg, Denmark. Antibakterielle Eigenschaften der Phenothiazine: Eine Behandlungsoption für die Zukunft? Chemotherapie Journal. 13.5. 2004: 203-205. Wissenschaftliche Verlagsgesesellschaft mbH. 21 August 2005. PDF. PubChem Substance Summary: Phenothiazine National Center for Biotechnology Information. Retrieved from http://en..org/wiki/Phenothiazine Categories: Phenothiazines Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Français Italiano Polski РуÑ?Ñ?кий Svenska ä¸æ–‡ This page was last modified on 3 August 2008, at 01:05
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