Metopimazine

Metopimazine

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 Y
UNII	238S75V9AV Y
ChEMBL	CHEMBL398615 Y
Chemical data
Formula	C22H27N3O3S2
Mol. mass	445.6 g/mol
SMILES O=S(=O)(c2cc1N(c3c(Sc1cc2)cccc3)CCCN4CCC(C(=O)N)CC4)C
InChI InChI=1S/C22H27N3O3S2/c1-30(27,28)17-7-8-21-19(15-17)25(18-5-2-3-6-20(18)29-21)12-4-11-24-13-9-16(10-14-24)22(23)26/h2-3,5-8,15-16H,4,9-14H2,1H3,(H2,23,26) Y Key:BQDBKDMTIJBJLA-UHFFFAOYSA-N Y
N (what is this?)  (verify)

Metopimazine (INN) is a phenothiazine antiemetic.

Synthesis

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 ().^[1]

References