Carfenazine

Chemical compound From Wikipedia, the free encyclopedia

Carfenazine (INN; former development code WY-2445; BAN carphenazine; USAN carphenazine maleate; brand name Proketazine; former development code NSC-71755) is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market.[1][2][3]

Other namesProketazine, Carphenazin
License data
Routes of
administrationOral
ATC code
  • none
Quick facts Clinical data, Other names ...
Carfenazine
Clinical data
Other namesProketazine, Carphenazin
License data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Withdrawn
Identifiers
  • 1-(10-{3-[4-(2-Hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)propan-1-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.018.249 Edit this at Wikidata
Chemical and physical data
FormulaC24H31N3O2S
Molar mass425.59 g·mol−1
3D model (JSmol)
  • CCC(=O)c1ccc2Sc3ccccc3N(CCCN4CCN(CCO)CC4)c2c1
  • InChI=1S/C24H31N3O2S/c1-2-22(29)19-8-9-24-21(18-19)27(20-6-3-4-7-23(20)30-24)11-5-10-25-12-14-26(15-13-25)16-17-28/h3-4,6-9,18,28H,2,5,10-17H2,1H3
  • Key:XZSMZRXAEFNJCU-UHFFFAOYSA-N
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Synthesis

Thieme Synthesis:[4] Patent:[5][6]

The alkylation reaction between 2-propionyl phenothiazine (1) and 1-bromo-3-chloropropane (2) gives 1-[10-(3-chloropropyl)phenothiazin-2-yl]propan-1-one (3). A second alkylation step, this time with 2-(1-Piperazinyl)ethanol (4), completes the synthesis of carfenazine (5).

Although above procedure is proof-of-concept, bear in mind no protecting group.[clarification needed] Other patent uses ketalization technique.[clarification needed]

Analogs

References

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