Phenothiazine: Difference between revisions
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'''Phenothiazine''' (a [[benzo]] derivative of [[thiazine]]) is a [[pesticide]] and industrial chemical used in pharmaceutical manufacturing. It is sometimes used as an [[antihelminthic]]. It was introduced by [[DuPont]] as an [[insecticide]] in [[1935]].<ref name=insecticide>[http://entweb.clemson.edu/pesticid/history.htm History of Insecticides and Control Equipment] Clemson University Pesticide Information Program.</ref> It is now most commonly used as an intermediate chemical in the manufacture of various [[psychiatry|psychiatric]] drugs. |
'''Phenothiazine''' (a [[benzo]] derivative of [[thiazine]]) is a [[pesticide]] and industrial chemical used in pharmaceutical manufacturing. It is sometimes used as an [[antihelminthic]]. It was introduced by [[DuPont]] as an [[insecticide]] in [[1935]].<ref name=insecticide>[http://entweb.clemson.edu/pesticid/history.htm History of Insecticides and Control Equipment] Clemson University Pesticide Information Program.</ref> It is now most commonly used as an intermediate chemical in the manufacture of various [[psychiatry|psychiatric]] drugs. Phenothiazine [[insecticide]] causes an abnormal amount of [[acetylcholine]] to build up in the insect thus exterminating it. Like phenothiazine [[insecticide]] the mode of action of [[nerve gas]] also is to cause an abnormal amount of [[acetylcholine]] to build up. Similarly a side effect of phenothiazine [[antipsychotics]] is anticholinergic blocking. |
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==Phenothiazine-derivative drugs== |
==Phenothiazine-derivative drugs== |
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Revision as of 03:34, 3 June 2007
| 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 (a benzo derivative of thiazine) is a pesticide and industrial chemical used in pharmaceutical manufacturing. It is sometimes used as an antihelminthic. It was introduced by DuPont as an insecticide in 1935.[1] It is now most commonly used as an intermediate chemical in the manufacture of various psychiatric drugs. Phenothiazine insecticide causes an abnormal amount of acetylcholine to build up in the insect thus exterminating it. Like phenothiazine insecticide the mode of action of nerve gas also is to cause an abnormal amount of acetylcholine to build up. Similarly a side effect of phenothiazine antipsychotics is anticholinergic blocking.
Phenothiazine-derivative drugs
The word "phenothiazines" is used to describe the largest of the five main classes of antipsychotic drugs. Although these drugs are generally effective, there are often serious side effects including tardive dyskinesia, akathisia and sedation (especially in the early stages of treatment).
There are three groups of phenothiazines, differing by their chemical structure and their pharmacological effects:
| Group | Autonomic | Example | Sedative | Extrapyramidal side-effect |
| Aliphatic compounds | ||||
| moderate | Chlorpromazine (Thorazine, Largactil) | strong | moderate | |
| Promazine | moderate | moderate | ||
| Triflupromazine (Vesprin) | strong | moderate/strong | ||
| Levomepromazine (Nozinan) | extremely strong | low | ||
| Piperidines | strong | Mesoridazine | strong | weak |
| Thioridazine (Mellaril) | strong | weak | ||
| Piperazines | weak | Fluphenazine | weak/moderate | strong |
| Perphenazine | weak/moderate | strong | ||
| Prochlorperazine (Compazine, Stemetil) | ||||
| Trifluoperazine (Stelazine) | moderate | strong |
References
- ^ History of Insecticides and Control Equipment Clemson University Pesticide Information Program.
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.