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Phenothiazine derivatives

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Phenothiazine
Phenothiazin
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]

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]

Phenothiazine-derivative drugsEdit

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


See alsoEdit

ReferencesEdit

  1. Whitaker R (2004). The case against antipsychotic drugs: a 50-year record of doing more harm than good. Med. Hypotheses 62 (1): 5-13.
  2. History of Insecticides and Control Equipment Clemson University Pesticide Information Program.
  3. "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

Further readingEdit

External linksEdit

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