Everything about Phenothiazines totally explained
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Phenothiazine, also called dibenzothiazine or thiodiphenylamine is a yellow or green crystalline 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 benzo derivative of
thiazine although thiazine itself isn't 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.
Overview
It is commonly used as an intermediate chemical in the manufacture of various
antipsychotic neuroleptic psychotropic drugs. It originally was developed as a synthetic dye in 1883, and it was introduced by
DuPont as an
insecticide in
1935. It is sometimes used as an
antihelminthic in livestock. It is used as an industrial chemical in the manufacture of rubber additives.
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.
Phenothiazine is also a potent alpha-
adrenergic blocking agent.
Synonyms for the chemical phenothiazine
Dibenzoparathiazine; Thiodiphenylamine; AFI-Tiazin; Agrazine; Antiverm; Biverm; Dibenzothiazine; Orimon; Lethelmin; Souframine; Nemazene; Vermitin; Padophene; Fenoverm; Phenovarm; Fentiazine; Contaverm; Fenothiazine, Ieeno; ENT 38; Helmetina; Helmetine, Penthazine; XL-50; Wurm-thional; Fentiazin; Padophene; Phenegic; Phenovis; Phenoxur; Reconox, Phenergan, Protazine; Thiergan
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.
The phenothiazine class of neuroleptic antipsychotic psychotropics are 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. They are the
aliphatic compounds, the
piperidines and
piperazines. An
aliphatic compound,
piperidine or
piperazine functional group is added to the phenothiazine molecule for the purpose of enhancing absorption and bioavailability of the phenothiazine chemical.
| 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 |
Further Information
Get more info on 'Phenothiazines'.
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