Fipexide
- N06BX05 (WHO)
- 1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-
2-(4-chlorophenoxy)ethanone
- 34161-24-5 Y
- 3351
- 3234 Y
- TG44VME01D
- D07345 Y
- ChEMBL254857 Y
- DTXSID5044657
- Interactive image
- 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 Y
- Key:BFUJHVVEMMWLHC-UHFFFAOYSA-N Y
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].
Synthesis
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
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Anon., FR 7524M (1969-12-15).
- ^ Gian P. Gardini, Giancarlo Scapini, Armando Raimondi, Placido Poidomani, U.S. patent 4,225,714 (1980 to Farmaceutici Geymonat Sud S.P.A.).
- v
- t
- e
(no additional rings)
- 2C-B-PP
- 3,4-CFP
- Acaprazine
- Antrafenine
- Aripiprazole
- Batoprazine
- Bifeprunox
- BRL-15,572
- Ciprofloxacin
- CSP-2503
- Dapiprazole
- DCPP
- DMPP
- Diphenylpiperazine
- Dropropizine
- EGIS-12,233
- Elopiprazole
- Eltoprazine
- Enpiprazole
- Ensaculin
- Etoperidone
- Flesinoxan
- Fluanisone
- Flibanserin
- Fluprazine
- Itraconazole
- Ketoconazole
- Levodropropizine
- Lorpiprazole
- mCPP
- Mefway
- MeOPP
- Mepiprazole
- Naftopidil
- Naluzotan
- Naphthylpiperazine
- Nefazodone
- Niaprazine
- Oxypertine
- Pardoprunox
- pCPP
- pFPP
- Posaconazole
- S-14,506
- S-14,671
- S-15,535
- SB-258,585
- SB-271,046
- SB-357,134
- SB-399,885
- Sonepiprazole
- TFMPP
- Tolpiprazole
- Trazodone
- Urapidil
- Vesnarinone
- Vilazodone
- Vortioxetine
- WAY-100,135
- WAY-100,635
(benzhydrylalkylpiperazines)
- AD-1211
- Almitrine
- Amperozide
- BRL-15,572
- Buclizine
- BW373U86
- Cetirizine
- Chlorbenzoxamine
- Chlorcyclizine
- Cinnarizine
- Clocinizine
- Cyclizine
- DBL-583
- Diphenpipenol
- Diphenylmethylpiperazine
- Dotarizine
- DPI-221
- DPI-287
- DPI-3290
- GBR-12,783
- GBR-12,935
- GBR-13,069
- GBR-13,098
- GBR-13,119
- Hydroxyzine
- JJC8-088
- Lidoflazine
- Manidipine
- Meclozine
- MT-45
- Oxatomide
- SNC-80
- Vanoxerine
(piperazine attached via side chain)
- Amoxapine
- Clopenthixol
- Clorotepine
- Clozapine
- Cyanothepin
- Doclothepin
- Docloxythepin
- Flupentixol
- Fluphenazine
- Isofloxythepin
- Loxapine
- Meperathiepin
- Metitepine
- Octomethothepin
- Olanzapine
- Opipramol
- Oxyclothepin
- Oxyprothepin
- Peradithiepin
- Perathiepin
- Perazine
- Perphenazine
- Pirenzepine
- Prochlorperazine
- Thiethylperazine
- Thiothixene
- Trifluoperazine
- Trifluthepin
- Zuclopenthixol