Phenothiazine
Heterocyclic compound containing a ring of four carbon, one nitrogen and one sulfur atom / From Wikipedia, the free encyclopedia
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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.
Quick Facts Names, Identifiers ...
Names | |
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Preferred IUPAC name
10H-Phenothiazine[1] | |
Other names
Thiodiphenylamine Dibenzothiazine Dibenzoparathiazine 10H-dibenzo-[b,e]-1,4-thiazine PTZ | |
Identifiers | |
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3D model (JSmol) |
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143237 | |
ChEBI | |
ChEMBL | |
ChemSpider |
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ECHA InfoCard | 100.001.997 |
EC Number |
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KEGG |
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PubChem CID |
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RTECS number |
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UNII | |
CompTox Dashboard (EPA) |
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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: | |
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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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.