Fipexide - CAS 34161-24-5
Catalog number: 34161-24-5
Category: Inhibitor
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Molecular Formula:
C20H21ClN2O4
Molecular Weight:
388.85
COA:
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Targets:
Dopamine Receptor
Description:
Fipexide hydrochloride is a nootropic agent that displays a positive effect on cognitive function
Purity:
≥98%
Appearance:
White Solid
Synonyms:
1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone;
Solubility:
Soluble in DMSO
Storage:
Store at RT.
MSDS:
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Application:
A nootropic drug, mainly for the treatment of senile dementia
Quality Standard:
Enterprise Standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Grams-Kilos
Density:
1.342 g/cm3
InChIKey:
BFUJHVVEMMWLHC-UHFFFAOYSA-N
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
Canonical SMILES:
C1CN(CCN1CC2=CC3=C(C=C2)OCO3)C(=O)COC4=CC=C(C=C4)Cl
1.Studies on the metabolism and the toxicological analysis of the nootropic drug fipexide in rat urine using gas chromatography-mass spectrometry.
Staack RF;Maurer HH J Chromatogr B Analyt Technol Biomed Life Sci. 2004 May 25;804(2):337-43.
Qualitative studies are described on the metabolism and the toxicological analysis of the nootropic fipexide (FIP) in rat urine using gas chromatography-mass spectrometry (GC-MS). FIP was extensively metabolized to 1-(3,4-methylenedioxybenzyl)piperazine (MDBP), 4-chlorophenoxyacetic acid, 1-[2-(4-chlorophenoxy)acetyl]piperazine, N-(4-hydroxy-3-methoxy-benzyl)piperazine, piperazine, N-(3,4-methylenedioxybenzyl)ethylenediamine, and N-[2-(4-chlorophenoxy)acetyl]ethylenediamine. The authors' systematic toxicological analysis (STA) procedure using full-scan GC-MS after acid hydrolysis of one urine aliquot, liquid-liquid extraction and acetylation allowed the detection of FIP via its metabolites in rat urine after administration of a common FIP dose. Therefore, this qualitative procedure should also be suitable for detection of a FIP intake in human urine. Differentiation of an intake of FIP from that of other drugs which form common metabolites is discussed.
2.Release of met-enkephalin from rat striatal slices: effect of amphetamine and fipexide.
Lucchi L;Govoni S;Spano PF;Trabucchi M Brain Res. 1986 Nov 19;398(1):212-4.
The release of Met-enkephalin immunoreactive material (ME-IR) from rat striatal slices is affected by exposure to amphetamine and fipexide (chloro-4-phenoxy)-2-acetyl-1-(methylene-dioxy 3, 4-benzyl-4-piperazine) a psychostimulant drug with mild dopaminomimetic activity. Both amphetamine and fipexide inhibited in vitro the release of ME-IR. The same effect was observed after in vivo acute administration and is also maintained after chronic treatment. The action of fipexide and amphetamine is still present after reserpine pretreatment. The results indicate that fipexide may facilitate dopamine neurotransmission by inhibition of an enkephalinergic inhibitory feed-back circuit.
3.Determining protein adducts of fipexide: mass spectrometry based assay for confirming the involvement of its reactive metabolite in covalent binding.
Sleno L;Varesio E;Hopfgartner G Rapid Commun Mass Spectrom. 2007;21(24):4149-57.
Fipexide is a nootropic drug, withdrawn from the market due to its idiosyncratic drug reactions causing adverse effects in man. Previous work on its metabolites has identified several potential reactive metabolites which could be implicated in protein binding. Here, we investigated the formation of these metabolites in rat and human hepatocytes. Based on these results, the o-quinone of fipexide (FIP), formed via the demethylenation reaction through a catechol intermediate, was chosen for further investigation. Studies were then pursued in order to relate this metabolite to protein binding, and thus better understand potential mechanisms for the toxicity of the parent compound. An assay was developed for determining the fipexide catechol-cysteine adduct in the microsomal protein fractions following in vitro incubations. This method digests the entire protein fraction into amino acids, followed by the detection of the Cys-metabolite adduct by liquid chromatography/mass spectrometry (LC/MS). We have designed a strategy where drug metabolism taking place in microsomal incubations and involved in protein binding can be assessed after the proteins have been digested, with the detection of the specific amino acid adduct.
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CAS 34161-24-5 Fipexide

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