Fipexide (Attentil, Vigilor) is a

psychoactive drug A psychoactive drug, psychopharmaceutical, mind-altering drug, consciousness-altering drug, psychoactive substance, or psychotropic substance is a chemical substance that alters psychological functioning by modulating central nervous system acti ...

of the

piperazine Piperazine () is an organic compound with the formula . In term of its structure, it can be described as cyclohexane with the 1- and 4-CH2 groups replaced by NH. Piperazine exists as deliquescent solid with a saline taste. Piperazine is freely sol ...

chemical class Chemical classification systems attempt to classify elements or compounds according to certain chemical functional or structural properties. Whereas the structural properties are largely intrinsic, functional properties and the derived classi ...

which was developed in

Italy Italy, officially the Italian Republic, is a country in Southern Europe, Southern and Western Europe, Western Europe. It consists of Italian Peninsula, a peninsula that extends into the Mediterranean Sea, with the Alps on its northern land b ...

in 1983. It was used as a

nootropic Nootropics ( or ) (colloquially brain supplements, smart drugs, cognitive enhancers, memory enhancers, or brain boosters) are chemical substances which purportedly improve cognitive functions, such as attention, memory, wakefulness, and self ...

drug in Italy and

France France, officially the French Republic, is a country located primarily in Western Europe. Overseas France, Its overseas regions and territories include French Guiana in South America, Saint Pierre and Miquelon in the Atlantic Ocean#North Atlan ...

, 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 Fever or pyrexia in humans is a symptom of an anti-infection defense mechanism that appears with Human body temperature, body temperature exceeding the normal range caused by an increase in the body's temperature Human body temperature#Fever, s ...

and

hepatitis Hepatitis is inflammation of the liver parenchyma, liver tissue. Some people or animals with hepatitis have no symptoms, whereas others develop yellow discoloration of the skin and whites of the eyes (jaundice), Anorexia (symptom), poor appetite ...

. Fipexide is similar in action to other nootropic drugs such as

piracetam Piracetam is a drug that has efficacy in cognitive disorders, vertigo, cortical myoclonus, dyslexia, and sickle cell anemia; sources differ on its usefulness for dementia. Piracetam is sold as a medication in many European countries. 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

PTC alkylation of

(1) with 2 equivalents of piperonyl chloride 5054-53-9(2) in the presence of cetrimonium bromide gives 1,4-bis-piperonylpiperazine 5436-41-4(3). Base catalyzed treatment with 4-Chlorophenoxyacetic acid (4) displaces one of the piperonyl groups to give fipexide (5).

References

{{Piperazines Nootropics Benzodioxoles Benzylpiperazines Carboxamides 4-Chlorophenyl compounds Hepatotoxins Phenol ethers Serotonin-norepinephrine-dopamine releasing agents

Synthesis

See also

References