Fipexide

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Chemical compound

title: "Fipexide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["nootropics", "benzodioxoles", "benzylpiperazines", "carboxamides", "4-chlorophenyl-compounds", "hepatotoxins", "phenol-ethers", "serotonin-norepinephrine-dopamine-releasing-agents"] description: "Chemical compound" topic_path: "general/nootropics" source: "https://en.wikipedia.org/wiki/Fipexide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| verifiedrevid = 443216648 | IUPAC_name = 1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]- 2-(4-chlorophenoxy)ethanone | image = Fipexide.svg | image_class = skin-invert-image

| tradename = | pregnancy_AU = | pregnancy_US = | legal_AU = | legal_CA = | legal_UK = | legal_US =

| CAS_number_Ref = | CAS_number = 34161-24-5 | ATC_prefix = N06 | ATC_suffix = BX05 | PubChem = 3351 | DrugBank_Ref = | ChemSpiderID_Ref = | ChemSpiderID = 3234 | UNII_Ref = | UNII = TG44VME01D | KEGG_Ref = | KEGG = D07345 | ChEMBL_Ref = | ChEMBL = 254857

| C=20 | H=21 | Cl=1 | N=2 | O=4 | smiles = Clc4ccc(OCC(=O)N1CCN(CC1)Cc2ccc3OCOc3c2)cc4 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = BFUJHVVEMMWLHC-UHFFFAOYSA-N

Fipexide (Attentil, Vigilor) is a psychoactive drug of the piperazine chemical class which was developed in Italy in 1983. It was used as a nootropic drug in Italy and France, mainly for the treatment of senile dementia, but is no longer in common use due to the occurrence of rare adverse drug reactions including fever 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.

Synthesis

::figure[src="https://upload.wikimedia.org/wikipedia/commons/d/d7/Fipexide_synthesis.svg" caption="4225714}} (1980 to Farmaceutici Geymonat Sud S.P.A.)."] ::

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).

References

References

  1. (February 1983). "[Fipexide: a new drug for the regulation of dopaminergic system at the macromolecular level]". Bollettino Chimico Farmaceutico.
  2. (1986). "Fipexide, an effective cognition activator in the elderly: a placebo-controlled, double-blind clinical trial". Current Medical Research and Opinion.
  3. (1990). "[Fever caused by fipexide. Evaluation of the national pharmacovigilance survey]". Therapie.
  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., {{Cite patent. FR. 7524M (1969-12-15).
  6. Gian P. Gardini, Giancarlo Scapini, Armando Raimondi, Placido Poidomani, {{US patent. 4225714 (1980 to Farmaceutici Geymonat Sud S.P.A.).

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nootropicsbenzodioxolesbenzylpiperazinescarboxamides4-chlorophenyl-compoundshepatotoxinsphenol-ethersserotonin-norepinephrine-dopamine-releasing-agents