Sulforidazine

Sulforidazine (Imagotan, Psychoson, Inofal) a typical antipsychotic and a metabolite of thioridazine; it and mesoridazine are more potent than the parent compound, whose pharmacological effects are believed by some to be largely due to its metabolism into sulforidazine and mesoridazine.^[1]

Sulforidazine

Clinical data
ATC code	none
Identifiers
IUPAC name 10-{2-[(RS)-1-Methylpiperidin-2-yl]ethyl}-2-(methylsulfonyl)-10H-phenothiazine
CAS Number	14759-06-9 N
PubChem CID	31765
ChemSpider	29458 Y
UNII	B7599I244X
ChEBI	CHEBI:135644
ChEMBL	ChEMBL2107268
CompTox Dashboard (EPA)	DTXSID30864531
ECHA InfoCard	100.035.274
Chemical and physical data
Formula	C21H26N2O2S2
Molar mass	402.57 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=S(=O)(c2cc1N(c3c(Sc1cc2)cccc3)CCC4N(C)CCCC4)C
InChI InChI=1S/C21H26N2O2S2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)26-21-11-10-17(15-19(21)23)27(2,24)25/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3 Y Key:FLGCRGJDQJIJAW-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Synthesis

Synthesis of sulforidazine

Sulforidazine can be synthesized starting 2-bromo-2'-amino-4'-methylsulfonyl-diphenyl sulfide (1).^[2][3][4] Acetylation produces 2-bromo-2'-acetamino-4'-methylsulphonyl diphenylsulfide (2), which is then alkylated with 2-(2-chloroethyl)-1-methylpiperidine (3). Deacylation followed by a copper-catalyzed ring-formation reaction produces sulforidazine.