Phenothiazine

Phenothiazine
Names
Preferred IUPAC name
10H-Phenothiazine[1]
Other names
Thiodiphenylamine
Dibenzothiazine
Dibenzoparathiazine
10H-dibenzo-[b,e]-1,4-thiazine
PTZ
Identifiers
3D model (JSmol)
143237
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.997 Edit this at Wikidata
EC Number
  • 202-196-5
KEGG
RTECS number
  • SN5075000
UNII
  • InChI=1S/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H checkY
    Key: WJFKNYWRSNBZNX-UHFFFAOYSA-N checkY
  • 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
  • c1ccc2c(c1)Nc3ccccc3S2
Properties
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)
0.00051 g/L (20 °C)[2]
Solubility in other solvents benzene, ether, petroleum ether, chloroform, hot acetic acid, ethanol (slightly), mineral oil (slightly)
Acidity (pKa) approx 23 in DMSO
−114.8·10−6 cm3/mol
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Warning
H302, H317, H373, H412
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[3]
REL (Recommended)
 TWA 5 mg/m3 [skin]
IDLH (Immediate danger)
 N.D.[3]
Pharmacology
QP52AX03 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

  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.
  3. ^ a b NIOSH Pocket Guide to Chemical Hazards. "#0494". National Institute for Occupational Safety and Health (NIOSH).