Phenothiazine derivatives
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| Phenothiazine | |
|---|---|
| |
| General | |
| Systematic name | 10H-phenothiazine |
| Other names | thiodiphenylamine, dibenzothiazine |
| Molecular formula | C12H9NS |
| SMILES | ? |
| Molar mass | 199.2762 g/mol |
| Appearance | yellow rhombic leaflets or
diamond-shaped plates |
| CAS number | 92-84-2 |
| Properties | |
| Density and phase | ? g/cm3, solid at STP |
| Soluble | benzene, ether, hot acetic acid,
ethanol (slightly), mineral oil (slightly) |
| Insoluble | water, petroleum ether, chloroform |
| Melting point | 185 °C |
| Boiling point | 371 °C |
| Acidity (pKa) | approx 23 in DMSO |
| Basicity (pKb) | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Phenothiazine is a benzo derivative of thiazine now most commonly used as an intermediate chemical in the manufacture of various psychiatric drugs. It originally was developed as a synthetic dye in 1883[1], and it was introduced by DuPont as an insecticide in 1935.[2] It is sometimes used as an antihelminthic in livestock.
Phenothiazine pesticides work by affecting the nervous system of insects, inhibiting the breakdown of acetylcholine by disabling the enzyme acetylcholinesterase. Many of the side effects of phenothiazine neuroleptic antipsychotics are due to their anticholinergic blocking effects. [3]
Contents |
[edit] 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.
The phenothiazine class of neuroleptic antipsychotic psychotropics is closely related to the thioxanthenes which are very similar pharmacologically.
There are three groups of phenothiazine antipsychotics, differing by their chemical structure and their pharmacological effects:
| 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, 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, Etrafon) | weak/moderate | strong | ||
| Flupentixol (sold as Depixol, Fluanxol) | moderate | strong | ||
| Prochlorperazine (trade names Compazine, Stemetil) | ||||
| Trifluoperazine (trade name Stelazine) | moderate | strong |
[edit] References
- ↑ Whitaker R (2004). The case against antipsychotic drugs: a 50-year record of doing more harm than good. Med. Hypotheses 62 (1): 5-13.
- ↑ History of Insecticides and Control Equipment Clemson University Pesticide Information Program.
- ↑ "Facts and Comparisons" III W. Port Plaza, Suite 300 St. Louis MO. USA 63146-3098 (telephone 314-216-2100 or 1-800-223-0554). The updatable section called "Antipsychotic Agents" is (c)1990
[edit] 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.
[edit] External links
| This page uses content from the English-language version of Wikipedia. The original article was at Phenothiazine. The list of authors can be seen in the page history. As with Psychology Wiki, the text of Wikipedia is available under the GNU Free Documentation License. |
