Befuraline

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Befuraline
Befuraline.svg
Clinical data
ATC code
  • none
Identifiers
  • 1-benzofuran-2-yl(4-benzylpiperazin-1-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H20N2O2
Molar mass 320.392 g·mol−1
3D model (JSmol)
  • O=C(N1CCN(CC1)CC2=CC=CC=C2)C3=CC4=C(C=CC=C4)O3
  • 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 Yes check.svgY
  • Key:SRIJFPBZWUFLFD-UHFFFAOYSA-N Yes check.svgY
   (verify)

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.

Contents

Synthesis

ChemDrug Synthesis: Patent: Befuraline synthesis.svg
ChemDrug Synthesis: Patent:

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). The conditions are Schotten-Baumann amidation.

See also

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References

  1. 1 2 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. Unterhalt, B.; Befuraline Hydrochloride. Drugs Fut 1978, 3, 6, 426.
  4. DE2157424 idem Rolf-Ortwin Weber, Alfons Soder, Istvan Boksay, U.S. Patent 4,374,990 (1980 to Hoechst Aktiengesellschaft).