Phenothiazine

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 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	143237
ChEBI	CHEBI:37931 ;
ChEMBL	ChEMBL828 ;
ChemSpider	21106365 ;
ECHA InfoCard	100.001.997
EC Number	202-196-5;
KEGG	D02601 ;
PubChem CID	7108;
RTECS number	SN5075000;
UNII	GS9EX7QNU6 ;
CompTox Dashboard (EPA)	DTXSID5021126 ;
	InChI InChI=1S/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H Key: WJFKNYWRSNBZNX-UHFFFAOYSA-N ; 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
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H317, H373, H412
Precautionary statements	P260, P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P314, P321, P330, P333+P313, P363, P501
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 5 mg/m3 [skin]
IDLH (Immediate danger)	N.D.
Pharmacology
ATCvet code	QP52AX03 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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. Derivatives of phenothiazine are highly bioactive and have widespread use and rich history.

The derivatives chlorpromazine and promethazine revolutionized the fields of psychiatry and allergy treatment, respectively. An earlier derivative, methylene blue, was one of the first antimalarial drugs, and derivatives of phenothiazine are currently under investigation as possible anti-infective drugs. Phenothiazine is a prototypical pharmaceutical lead structure in medicinal chemistry.

^ "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 216. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ "Sigma-Aldrich catalog of Phenothiazine". Retrieved 2022-02-28.
^ ^a ^b NIOSH Pocket Guide to Chemical Hazards. "#0494". National Institute for Occupational Safety and Health (NIOSH).

[iupac2013-1] "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 216. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[2] "Sigma-Aldrich catalog of Phenothiazine". Retrieved 2022-02-28.

[PGCH-3] NIOSH Pocket Guide to Chemical Hazards. "#0494". National Institute for Occupational Safety and Health (NIOSH).

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