Piberaline

Piberaline (EGYT-475; Trelibet) is a psychoactive drug and member of the piperazine chemical class which was developed in the 1980s. It has stimulant and antidepressant effects which are thought to be due largely to its active metabolite benzylpiperazine.[1] It was researched to a limited extent in Hungary and Spain, but was not widely accepted and does not seem to be in current use, although a closely related drug befuraline with similar effects has been slightly more successful.

Piberaline
Clinical data
Trade namesTrelibet
ATC code
  • none
Identifiers
IUPAC name
  • [4-(phenylmethyl)piperazin-1-yl]-pyridin-2-ylmethanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H19N3O
Molar mass281.359 g·mol−1
3D model (JSmol)
SMILES
  • C1CN(CCN1CC2=CC=CC=C2)C(=O)C3=CC=CC=N3
InChI
  • InChI=1S/C17H19N3O/c21-17(16-8-4-5-9-18-16)20-12-10-19(11-13-20)14-15-6-2-1-3-7-15/h1-9H,10-14H2
  • Key:TZFUBYYADABEAV-UHFFFAOYSA-N
  (verify)

Synthesis
Patent:[2] ~99%:[3] ~75%:[4]

2-Chloropyridine, carbon monoxide & BZP reacted together.

Or from picolinic acid & BZP.

See also

References
  1. Tekes K, Tóthfalusi L, Malomvölgyi B, Hermán F, Magyar K (1987). "Studies on the biochemical mode of action of EGYT-475, a new antidepressant". Polish Journal of Pharmacology and Pharmacy. 39 (2): 203–11. PMID 2448760.
  2. Jenoe Dr. Koroesi, 5 More », DE 2215545 (1975 to Egyt Gyogyszervegyeszeti Gyar, Budapest).
  3. Kumar, Kamal; Michalik, Dirk; Garcia Castro, Ivette; Tillack, Annegret; Zapf, Alexander; Arlt, Michael; Heinrich, Timo; Böttcher, Henning; Beller, Matthias (2004). "Biologically Active Compounds through Catalysis: Efficient Synthesis ofN-(Heteroarylcarbonyl)-N′-(arylalkyl) piperazines". Chemistry - A European Journal. 10 (3): 746–757. doi:10.1002/chem.200305327.
  4. Younes, S (2000). "Synthesis and structure–activity relationships of novel arylalkyl 4-benzyl piperazine derivatives as σ site selective ligands". European Journal of Medicinal Chemistry. 35 (1): 107–121. doi:10.1016/S0223-5234(00)00113-6.


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