Chlorproethazine
Chemical compound
From Wikipedia, the free encyclopedia
Chlorproethazine, sold under the brand name Neuriplege, is a drug of the phenothiazine group described as a muscle relaxant or tranquilizer which is or has been marketed in Europe as a topical cream for the treatment of muscle pain.[1][2][3][4][5] It has been associated with photoallergic contact dermatitis.[6][7]
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| Names | |
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| Preferred IUPAC name
3-(2-Chlorophenothiazin-10-yl)-N,N-diethylpropan-1-amine | |
| Other names
RP-4909 | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.001.373 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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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 their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
Chlorproethazine can be synthesized from a diphenylsulfide derivative. 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 the Ullmann condensation (i.e. the Goldberg reaction).