Metopimazine

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Metopimazine
Metopimazine.svg
Systematic (IUPAC) name
1-(3-[2-(methylsulfonyl)-10H-phenothiazin-10-yl]propyl)piperidine-4-carboxamide
Clinical data
AHFS/Drugs.com International Drug Names
Legal status ?
Identifiers
CAS number 14008-44-7 N
ATC code A04AD05
PubChem CID 26388
ChemSpider 24584 YesY
UNII 238S75V9AV YesY
ChEMBL CHEMBL398615 YesY
Chemical data
Formula C22H27N3O3S2 
Mol. mass 445.6 g/mol
 N (what is this?)  (verify)

Metopimazine (INN) is a phenothiazine antiemetic.

Synthesis[edit]

Metopimazine synthesis: DE 1092476  Jacob, R. M.; Robert, J. G.; 1959, .

The reduced basicity of phenothiazine nitrogen requires that even acylation proceed via the anion. The amide () from the methyl thioether () can be prepared, for example, by sequential reaction with sodium amide and acetic anhydride. Oxidation of that intermediate with peracid proceeds preferentially on the more electron-rich alkyl thioether to give the sulfone; this affords the phenothiazine () on hydrolysis of the amide. Complex side chains are most conveniently incorporated in a stepwise fashion. The first step in the present sequence involves reactionof () as its anion with 1-bromo-3-chloropropane to give (). The use of that halide with alkylate piperidine-4-carboxamide () affords the antipsychotic agent metopimazine ().

Methopromazine[edit]

Methopromazine synthesis: R. M. Jacob and J. G. Robert, U.S. Patent 2,837,518 (1958).

References[edit]