Fipexide

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 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.

Fipexide
Clinical data
ATC code
Identifiers
IUPAC name
  • 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
Chemical and physical data
FormulaC20H21ClN2O4
Molar mass388.85 g·mol−1
3D model (JSmol)
SMILES
  • Clc4ccc(OCC(=O)N1CCN(CC1)Cc2ccc3OCOc3c2)cc4
InChI
  • 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 Y
  • Key:BFUJHVVEMMWLHC-UHFFFAOYSA-N Y
  (verify)

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
  1. Missale C, Pasinetti G, Govoni S, Spano PF, Trabucchi M (February 1983). "[Fipexide: a new drug for the regulation of dopaminergic system at the macromolecular level]". Bollettino Chimico Farmaceutico (in Italian). 122 (2): 79–85. PMID 6871040.
  2. Bompani R, Scali G (1986). "Fipexide, an effective cognition activator in the elderly: a placebo-controlled, double-blind clinical trial". Current Medical Research and Opinion. 10 (2): 99–106. doi:10.1185/03007998609110426. PMID 3519097.
  3. Guy C, Blay N, Rousset H, Fardeau V, Ollagnier M (1990). "[Fever caused by fipexide. Evaluation of the national pharmacovigilance survey]". Therapie (in French). 45 (5): 429–31. PMID 2260037.
  4. Gardini, G. P.; Palla, G.; Scapini, G.; Cesaroni, M. R. (2006). "Convenient Synthesis of N-Benzyl-N′-acyl-piperazines". Synthetic Communications. 12 (11): 887–890. ISSN 0039-7911. doi:10.1080/00397918208065967.
  5. Anon., FR 7524M (1969-12-15).
  6. Gian P. Gardini, Giancarlo Scapini, Armando Raimondi, Placido Poidomani, U.S. Patent 4,225,714 (1980 to Farmaceutici Geymonat Sud S.P.A.).


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