Sulforidazine

Typical antipsychotic medication
  • none
Identifiers
  • 10-{2-[(RS)-1-Methylpiperidin-2-yl]ethyl}-2-(methylsulfonyl)-10H-phenothiazine
CAS Number
  • 14759-06-9 ☒N
PubChem CID
  • 31765
ChemSpider
  • 29458 checkY
UNII
  • B7599I244X
ChEBI
  • CHEBI:135644
ChEMBL
  • ChEMBL2107268
ECHA InfoCard100.035.274 Edit this at WikidataChemical and physical dataFormulaC21H26N2O2S2Molar mass402.57 g·mol−13D model (JSmol)
  • Interactive image
  • 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 checkY
  • Key:FLGCRGJDQJIJAW-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

Synthesis

Thieme Synthesis:[2] Patent:[3]

2-bromo-2'-amino-4'-methylsulphonyl-diphenyl Sulphide, CID:43448246 (1) 2-bromo-2'-acetamino-4'-methylsulphonyl diphenylsulphide (2) 2-(2-Chloroethyl)-1-Methylpiperidine [50846-01-0] (3)

References

  1. ^ Niedzwiecki DM, Mailman RB, Cubeddu LX (March 1984). "Greater potency of mesoridazine and sulforidazine compared with the parent compound, thioridazine, on striatal dopamine autoreceptors". Journal of Pharmacology and Experimental Therapeutics. 228 (3): 636–9. PMID 6707914.
  2. ^ Morrow, Ryan J.; Millership, Jeff S.; Collier, Paul S. (2005). "Facile Syntheses of the Three Major Metabolites of Thioridazine". Helvetica Chimica Acta. 88 (5): 962–967. doi:10.1002/hlca.200590089.
  3. ^ FR1363683 idem Bruschweiler Conrad, Schwarb Gustav, Winkler Hans, Renz Jany, U.S. patent 3,314,948 (1967 to Sandoz Ltd).
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