Fipexide

Title: Fipexide
CAS Registry Number: 34161-24-5
CAS Name: 1-(1,3-Benzodioxol-5-ylmethyl)-4-[(4-chlorophenoxy)acetyl]piperazine
Additional Names: 1-[(p-chlorophenoxy)acetyl]-4-piperonylpiperazine; 1-[2-(4-chlorophenoxy)acetyl]-4-(3,4-methylenedioxybenzyl)piperazine
Molecular Formula: C20H21ClN2O4
Molecular Weight: 388.84
Percent Composition: C 61.78%, H 5.44%, Cl 9.12%, N 7.20%, O 16.46%
Literature References: Prepn of hydrochloride: A. Buzas, R. Pierre, FR M7524 (1970 to Lab Bouchard), C.A. 75, 112865r (1971). Manufacturing process: G. P. Gardini et al., US 4225714 (1980 to Farmaceutici Geymon.). Improved prepn: G. P. Gardini et al., Synth. Commun. 12, 887 (1982). Determn by TLC: G. Musumarra et al., J. Chromatogr. 350, 151 (1985). Toxicology and pharmacology: G. David et al., Acta Ther. 11, 387 (1985). Clinical trial in the elderly: B. Bompani, G. Scali, Curr. Med. Res. Opin. 10, 99 (1986).
Derivative Type: Hydrochloride
CAS Registry Number: 34161-23-4
Manufacturers' Codes: BP-662
Trademarks: Attentil (Ravizza); Vigilor (Bouchard)
Molecular Formula: C20H21ClN2O4.HCl
Molecular Weight: 425.31
Percent Composition: C 56.48%, H 5.21%, Cl 16.67%, N 6.59%, O 15.05%
Properties: Crystals from ethanol, mp 230-232°. LD50 in Swiss mice, Sprague-Dawley rats, Wistar rats (mg/kg): 4150, 4482, 7000 orally; 499, 537, 450 i.p. (David).
Melting point: mp 230-232°
Toxicity data: LD50 in Swiss mice, Sprague-Dawley rats, Wistar rats (mg/kg): 4150, 4482, 7000 orally; 499, 537, 450 i.p. (David)
Therap-Cat: Nootropic.
Keywords: Nootropic.
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Fipexide
Fipexide.svg
Systematic (IUPAC) name
1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-
2-(4-chlorophenoxy)ethanone
Clinical data
Legal status  ?
Identifiers
CAS number 34161-24-5
ATC code N06BX05
PubChem CID 3351
ChemSpider 3234 YesY
UNII TG44VME01D YesY
KEGG D07345 YesY
ChEMBL CHEMBL254857 YesY
Chemical data
Formula C20H21ClN2O4 
Mol. mass 388.845 g/mol
 YesY (what is this?)  (verify)

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 is structurally similar to another more well-known nootropic, centrophenoxine. Chemically, it is an amide union of parachlorophenoxyacetate and methylenedioxybenzylpiperazine, and notably, has been shown to metabolize to the latter, which plays a significant role in its effects.