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| Phenothiazine | |
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| IUPAC name | 10H-phenothiazine |
| Other names | thiodiphenylamine, dibenzothiazine, dibenzoparathiazine, 10H-dibenzo-[b, e]-1,4-thiazine |
| 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 |
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Phenothiazine is the organic compound with the formula S(C6H4)2NH. This yellow tricyclic compound is soluble in acetic acid, benzene, and ether. The compound is related the thiazine-class of heterocyclic compounds. Derivatives of the parent compound find wide use as drugs.
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Synthesis
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.[1]
Non-drug applications
The synthetic dye methylene blue, containing the structure, was described in 1876. Phenothiazine itself was introduced by DuPont as an insecticide in 1935.[2] It is sometimes used as an antihelminthic in livestock.
Phenothiazine-derived drugs
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 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.[3]citation needed
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).
| 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
- ^ Gérard Taurand, "Phenothiazine and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
- ^ History of Insecticides and Control Equipment Clemson University Pesticide Information Program.
- ^ Rang; Dale et al, Pharmacology, 6th edition
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.
Appendix: tradenames for phenothiazine
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. [1]
Wikipedia content modification information:
- This page was last modified on 9 October 2008, at 15:18.
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