Phenothiazines

Phenothiazine

Names
Preferred IUPAC name 10H-Phenothiazine
Other names Thiodiphenylamine Dibenzothiazine Dibenzoparathiazine 10H-dibenzo-[b,e]-1,4-thiazine PTZ
Identifiers
CAS Number	92-84-2 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:37931 N
ChEMBL	ChEMBL828 Y
ChemSpider	21106365 Y
ECHA InfoCard	100.001.997
KEGG	D02601 Y
UNII	GS9EX7QNU6 Y
InChI InChI=1S/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H Y Key: WJFKNYWRSNBZNX-UHFFFAOYSA-N Y InChI=1/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H Key: WJFKNYWRSNBZNX-UHFFFAOYAI
SMILES c1ccc2c(c1)Nc3ccccc3S2
Properties
Chemical formula	C12H9NS
Molar mass	199.27 g/mol
Appearance	greenish-yellow rhombic leaflets or diamond-shaped plates
Melting point	185 °C (365 °F; 458 K)
Boiling point	371 °C (700 °F; 644 K)
Solubility in water	0.00051 g/L (20 °C)
Solubility in other solvents	benzene, ether, petroleum ether, chloroform, hot acetic acid, ethanol (slightly), mineral oil (slightly)
Acidity (pKa)	approx 23 in DMSO
Magnetic susceptibility (χ)	-114.8·10−6 cm3/mol
Hazards
US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	TWA 5 mg/m3 [skin]
IDLH (Immediate danger)	N.D.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Phenothiazine abbreviated PTZ is an organic compound that has the formula S(C₆H₄)₂NH and is related to the thiazine-class of heterocyclic compounds.

It is used in chemical manufacturing as a stabilizer or inhibitor. It was used in the mid-20th century as an insecticide and antihelminthic for livestock and humans, but was superseded by other compounds.

Derivatives of phenothiazine discovered in the 1940s revolutionized the field of psychiatry and allergy treatment. The earliest derivative, methylene blue, was one of the first antimalarial drugs, and as of 2015 derivatives are under investigation as possible anti-infective drugs. It is a prototypical pharmaceutical lead structure in modern medicinal chemistry.

In the manufacture of monomers, phenothiazine is used as a chemical stabilizer or inhibitor to prolong storage and shelf life of products such as acryloyl chloride.

Phenothiazine was formerly used as an insecticide and as a drug to treat infections with parasitic worms (antihelminthic) in and people, but its use for those purposes has been superseded by other chemicals.

Phenothiazine was introduced by DuPont as an insecticide in 1935. About 3,500,000 pounds were sold in the US in 1944. However, because it was degraded by sunlight and air, it was difficult to determine how much to use in the field, and its use waned in the 1940s with the arrival of new pesticides like DDT that were more durable. As of July 2015 it is not registered for pesticide use in the US, nor Europe, nor Australia.