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Phenothiazine is the organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the formula S(C6H4)2NH. This yellow tricyclic compound is soluble in acetic acid, benzene, and ether. The compound is related to the thiazine
Thiazine

Thiazines are organic compounds containing a ring of four carbon, one nitrogen and one sulfur atom. Chemicals that include thiazine are used for dyes, tranquilizers and insecticides....
-class of heterocyclic compound
Heterocyclic compound

Heterocyclic compounds are organic compounds containing at least one atom of carbon, and at least one element other than carbon, such as sulfur, oxygen or nitrogen within a ring structure....
s. Derivatives of the parent compound find wide use as drugs.

compound was originally prepared by Bernthsen in 1883 via the reaction of diphenylamine
Diphenylamine

Diphenylamine is the organic compound with the chemical formula 2NH. It is a colourless solid, but samples are often yellow due to oxidized impurities....
 with sulfur, but more recent syntheses rely on the cyclization of 2-substituted diphenylsulfide.






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Phenothiazine is the organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the formula S(C6H4)2NH. This yellow tricyclic compound is soluble in acetic acid, benzene, and ether. The compound is related to the thiazine
Thiazine

Thiazines are organic compounds containing a ring of four carbon, one nitrogen and one sulfur atom. Chemicals that include thiazine are used for dyes, tranquilizers and insecticides....
-class of heterocyclic compound
Heterocyclic compound

Heterocyclic compounds are organic compounds containing at least one atom of carbon, and at least one element other than carbon, such as sulfur, oxygen or nitrogen within a ring structure....
s. Derivatives of the parent compound find wide use as drugs.

Synthesis

The compound was originally prepared by Bernthsen in 1883 via the reaction of diphenylamine
Diphenylamine

Diphenylamine is the organic compound with the chemical formula 2NH. It is a colourless solid, but samples are often yellow due to oxidized impurities....
 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.

Non-drug applications

The synthetic dye methylene blue
Methylene blue

Methylene blue is a Heterocyclic ring aromaticity chemical compound with molecular formula: carbon16hydrogen18chlorinenitrogen3sulfur....
, containing the structure, was described in 1876. Phenothiazine itself was introduced by DuPont
DuPont

E. I. du Pont de Nemours and Company is an United States chemical industry that was founded in July 1802 as a gunpowder mill by Eleuth?re Ir?n?e du Pont....
 as an insecticide
Insecticide

An insecticide is a pesticide used against insects in all developmental forms. They include ovicides and larvicides used against the Egg and larvae of insects respectively....
 in 1935. It is sometimes used as an antihelminthic in livestock.

Phenothiazine-derived drugs

The phenothiazine structure occurs in various neuroleptic drugs, e.g. Chlorpromazine
Chlorpromazine

Chlorpromazine is a phenothiazine antipsychotic, and the oldest in the antipsychotic family of drugs. It is a typical antipsychotic. It is principally used in the treatment of schizophrenia, though it has also been used to treat severe manic episodes in people with bipolar disorder....
, and antihistaminic drugs, e.g. Promethazine
Promethazine

Promethazine is a first-generation histamine H1 receptor antagonist, antihistamine and antiemetic medication. It can also have strong sedative effects although it is rarely used specifically for this....
. The term "phenothiazines" describes the largest of the five main classes of neuroleptic antipsychotic drugs
Antipsychotic

Antipsychotics are a group of psychoactive drugs commonly but not exclusively used to treat psychosis, which is typified by schizophrenia. Over time a wide range of antipsychotics have been developed....
. These drugs have antipsychotic and, often, antiemetic
Antiemetic

An antiemetic is a medication that is effective against vomiting and nausea. Anti-emetics are typically used to treat motion sickness and the Adverse effect of opioid analgesics, general anaesthetics and chemotherapy directed against cancer....
 properties, although they may also cause severe side effects
Adverse drug reaction

An adverse drug reaction or adverse drug event is an expression that describes the unwanted, negative consequences associated with the use of given medications....
 such as akathisia
Akathisia

Akathisia, or acathisia, is a syndrome characterized by unpleasant sensations of "inner" restlessness that manifests itself with an inability to sit still or remain motionless, hence its origin in Ancient Greek a , [without, not] + ????s?? , [sitting]....
, tardive dyskinesia
Tardive dyskinesia

Tardive dyskinesia is a variety of Dyskinesia manifesting as a side effect of long-term or high-dose use of dopamine antagonists, usually antipsychotics....
, extrapyramidal symptoms, and the rare but potentially fatal neuroleptic malignant syndrome
Neuroleptic malignant syndrome

Neuroleptic malignant syndrome is a life-threatening neurological disorder most often caused by an adverse reaction to antipsychotic. It generally presents with muscle rigidity, fever, autonomic instability and cognitive changes such as delirium, and is associated with elevated creatine phosphokinase ....
 as well as substantial weight gain.

Phenothiazines are used as inodilators in congestive heart failure
Congestive heart failure

Heart failure is a condition in which a problem with the structure or function of the heart impairs its ability to supply sufficient blood flow to meet the body's needs....
, acting upon the type I calcium/calmodulin dependent phosphodiesterase
Phosphodiesterase

A phosphodiesterase is any enzyme that breaks a phosphodiester bond. Usually, people speaking of phosphodiesterase are referring to cyclic nucleotide phosphodiesterases, which have great clinical significance and are described below....
.

Phenothiazine antipsychotics are classified into three groups that differ with respect to the substituent on nitrogen: the aliphatic compound
Aliphatic compound

In organic chemistry, compounds composed of carbon and hydrogen are divided into two classes: aromatic compounds, which contain benzene rings or similar rings of atoms, and aliphatic compounds , which do not contain aromatic rings....
s (bearing acyclic
Acyclic

Acyclic can refer to:* in chemistry, a compound which is not Cyclic compound, e.g. alkanes and acyclic aliphatic compounds* in mathematics:** a directed acyclic graph...
 groups), the "piperidines" (bearing piperidine
Piperidine

Piperidine is an organic compound with the molecular formula 5NH. This heterocyclic compound amine consists of a six-membered ring containing five methylene units and one nitrogen atom....
-derived groups), and the piperazine (bearing piperazine
Piperazine

Piperazine is an organic compound that consists of a six-membered ring containing two opposing nitrogen atoms. Piperazine exists as small alkaline deliquescent crystals with a salt taste....
-derived substituents).




Further reading

  • Hendricks, Christensen, J.B., and Kristiansen, Jette E. Sonderborg, Denmark. "" Chemotherapie Journal. 13.5. (2004): 203–205. Wissenschaftliche Verlagsgesesellschaft mbH. 21 August 2005. (PDF).
  • 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.