Befuraline

Befuraline (DIV-154) is a psychoactive drug and member of the piperazine chemical class which was developed in Germany in the 1970s.[1] Befuraline has stimulant and antidepressant effects and has seen some use in Germany and France, although it has never become widely used.[2] Befuraline's active metabolite benzylpiperazine is likely to contribute to its effects.

Befuraline
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 1-benzofuran-2-yl(4-benzylpiperazin-1-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H20N2O2
Molar mass320.392 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N1CCN(CC1)CC2=CC=CC=C2)C3=CC4=C(C=CC=C4)O3
InChI
  • InChI=1S/C20H20N2O2/c23-20(19-14-17-8-4-5-9-18(17)24-19)22-12-10-21(11-13-22)15-16-6-2-1-3-7-16/h1-9,14H,10-13,15H2 Y
  • Key:SRIJFPBZWUFLFD-UHFFFAOYSA-N Y
  (verify)

Synthesis
Synthesis:[1] Patent:[3]

A one-step coupling between coumarilic acid (benzofuran-2-carboxylic acid) [496-41-3] (1) and benzylpiperazine (BzP) (2) gives an amide, and hence Befuraline (3).

See also

References
  1. Boksay IJ, Popendiker K, Weber RO, Söder A (1979). "Synthesis and pharmacological activity of befuraline (N-benzo[b]furan-2-ylcarbonyl-N'-benzylpiperazine), a new antidepressant compound". Arzneimittel-Forschung. 29 (2): 193–204. PMID 582130.
  2. Gastpar M, Gastpar G, Gilsdorf U (November 1985). "Befuraline, its safety and efficacy in depressed inpatients". Pharmacopsychiatry. 18 (6): 351–5. doi:10.1055/s-2007-1017396. PMID 4089015.
  3. DE2157424 idem Rolf-Ortwin Weber, Alfons Soder, Istvan Boksay, U.S. Patent 4,374,990 (1980 to Hoechst Aktiengesellschaft).


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