Fipexide

Chemical compound From Wikipedia, the free encyclopedia

Fipexide (Attentil, Vigilor) is a psychoactive drug of the piperazine chemical class which was developed in Italy in 1983.[1] It was used as a nootropic drug in Italy and France, mainly for the treatment of senile dementia,[2] but is no longer in common use due to the occurrence of rare adverse drug reactions including fever[3] and hepatitis. Fipexide is similar in action to other nootropic drugs such as piracetam[citation needed] and has a few similarities in chemical structure to centrophenoxine. Chemically, it is an amide union of parachlorophenoxyacetate and methylenedioxybenzylpiperazine (MDBZP), and has been shown to metabolize to the latter, which plays a significant role in its effects[citation needed].

ATC code
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Fipexide
Clinical data
ATC code
Identifiers
  • 1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-
    2-(4-chlorophenoxy)ethanone
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.047.128 Edit this at Wikidata
Chemical and physical data
FormulaC20H21ClN2O4
Molar mass388.85 g·mol−1
3D model (JSmol)
  • Clc4ccc(OCC(=O)N1CCN(CC1)Cc2ccc3OCOc3c2)cc4
  • InChI=1S/C20H21ClN2O4/c21-16-2-4-17(5-3-16)25-13-20(24)23-9-7-22(8-10-23)12-15-1-6-18-19(11-15)27-14-26-18/h1-6,11H,7-10,12-14H2 checkY
  • Key:BFUJHVVEMMWLHC-UHFFFAOYSA-N checkY
  (verify)
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Synthesis

Synthesis:[4] Patents:[5][6]

PTC alkylation of piperazine (1) with 2 equivalents of piperonyl chloride [25054-53-9] (2) in the presence of cetrimonium bromide gives 1,4-bis-piperonylpiperazine [55436-41-4] (3). Base catalyzed treatment with 4-Chlorophenoxyacetic acid (4) displaces one of the piperonyl groups to give fipexide (5).

See also

References

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