Befuraline
Psychoactive drug of the piperazine chemical class
- none
- 1-benzofuran-2-yl(4-benzylpiperazin-1-yl)methanone
- 41717-30-0 Y 41716-84-1
- 68664
- 61918 Y
- 787AQ35GHR
- ChEMBL1076256 Y
- DTXSID2046206
- Interactive image
- 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
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.
Synthesis
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
- ^ a b 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.
- ^ 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. S2CID 9322026.
- ^ DE2157424 idem Rolf-Ortwin Weber, Alfons Soder, Istvan Boksay, U.S. patent 4,374,990 (1980 to Hoechst Aktiengesellschaft).
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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