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| Names | |
|---|---|
| Preferred IUPAC name 3-(2-Chlorophenothiazin-10-yl)-N,N-diethylpropan-1-amine | |
| Other names RP-4909 | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.001.373 |
| KEGG |
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| UNII |
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| Properties | |
| C19H23ClN2S | |
| Molar mass | 346.91732 g/mol |
| Pharmacology | |
| N05AA07 (WHO) | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Chlorproethazine, sold under the brand nameNeuriplege, is adrug of thephenothiazine group described as amuscle relaxant ortranquilizer which is or has been marketed inEurope as atopicalcream for the treatment ofmuscle pain.[1][2][3][4][5] It has been associated withphotoallergiccontact dermatitis.[6][7]
Chlorproethazine can be synthesized from adiphenylsulfidederivative. The general scheme is sufficiently flexible to permit the interchange of the order of some of the steps.
Thus alkylation of 2-(2-bromo-phenylsulfanyl)-5-chloro-aniline [105790-02-1] (1) with 3-chloro-1-diethylaminopropane [104-77-8] (2) leads to the intermediate (3). Ring closure as above by nucleophilic aromatic displacement leads to the antipsychotic drug chlorproethazine (4).
The last step uses copper powder and is a form of theUllmann condensation (i.e. theGoldberg reaction).
