Metopimazine

Metopimazine

File:Metopimazine.svg
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A04AD05 (WHO)
Identifiers
IUPAC name 1-(3-[2-(methylsulfonyl)-10H-phenothiazin-10-yl]propyl)piperidine-4-carboxamide
CAS Number	14008-44-7 N
PubChem CID	26388
ChemSpider	24584 Y
UNII	238S75V9AV
ChEMBL	ChEMBL398615 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C22H27N3O3S2
Molar mass	445.6 g/mol
3D model (JSmol)	Interactive image
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
NY (what is this?)  (verify)

Metopimazine (INN) is a phenothiazine antiemetic.

Synthesis

File:Metopimazine synthesis.svg

Metopimazine synthesis:Jacob, R. M.; Robert, J. G.; Template:Patent (1959).

The reduced basicity of phenothiazine nitrogen requires that even acylation proceed via the anion. The amide (2) from the methyl thioether (2) 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 (3) on hydrolysis of the amide. Complex side chains are most conveniently incorporated in a stepwise fashion. The first step in the present sequence involves reaction of (3) as its anion with 1-bromo-3-chloropropane to give (4). The use of that halide with alkylate piperidine-4-carboxamide (5) affords the antipsychotic agent metopimazine (6).

Methopromazine

File:Methopromazine synthesis.png

Methopromazine synthesis: R. M. Jacob and J. G. Robert, Template:US Patent (1958).

References

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