Befuraline

Befuraline
Clinical data
ATC code	none;
Identifiers
	IUPAC name 1-benzofuran-2-yl(4-benzylpiperazin-1-yl)methanone;
CAS Number	41717-30-0 41716-84-1;
PubChem CID	68664;
ChemSpider	61918 ;
UNII	787AQ35GHR;
ChEMBL	ChEMBL1076256 ;
CompTox Dashboard (EPA)	DTXSID2046206 ;
Chemical and physical data
Formula	C20H20N2O2
Molar mass	320.392 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:SRIJFPBZWUFLFD-UHFFFAOYSA-N ;
	(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.

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).

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 582130.193-204&rft.date=1979&rft_id=info:pmid/582130&rft.aulast=Boksay&rft.aufirst=IJ&rft.au=Popendiker, K&rft.au=Weber, RO&rft.au=Söder, A&rfr_id=info:sid/en.wikipedia.org:Befuraline" class="Z3988">
^ 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 9322026.351-5&rft.date=1985-11&rft_id=https://api.semanticscholar.org/CorpusID:9322026#id-name=S2CID&rft_id=info:pmid/4089015&rft_id=info:doi/10.1055/s-2007-1017396&rft.aulast=Gastpar&rft.aufirst=M&rft.au=Gastpar, G&rft.au=Gilsdorf, U&rfr_id=info:sid/en.wikipedia.org:Befuraline" class="Z3988">
^ DE2157424 idem Rolf-Ortwin Weber, Alfons Soder, Istvan Boksay, U.S. patent 4,374,990 (1980 to Hoechst Aktiengesellschaft).

This psychoactive drug-related article is a stub. You can help Wikipedia by expanding it.

[pmid582130-1] 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 582130.193-204&rft.date=1979&rft_id=info:pmid/582130&rft.aulast=Boksay&rft.aufirst=IJ&rft.au=Popendiker, K&rft.au=Weber, RO&rft.au=Söder, A&rfr_id=info:sid/en.wikipedia.org:Befuraline" class="Z3988">

[pmid4089015-2] 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. S2CID 9322026.351-5&rft.date=1985-11&rft_id=https://api.semanticscholar.org/CorpusID:9322026#id-name=S2CID&rft_id=info:pmid/4089015&rft_id=info:doi/10.1055/s-2007-1017396&rft.aulast=Gastpar&rft.aufirst=M&rft.au=Gastpar, G&rft.au=Gilsdorf, U&rfr_id=info:sid/en.wikipedia.org:Befuraline" class="Z3988">

[3] DE2157424 idem Rolf-Ortwin Weber, Alfons Soder, Istvan Boksay, U.S. patent 4,374,990 (1980 to Hoechst Aktiengesellschaft).

[1]

[2]

[3]

Clinical data

ATC code	none
Identifiers
IUPAC name 1-benzofuran-2-yl(4-benzylpiperazin-1-yl)methanone
CAS Number	41717-30-0^Y 41716-84-1
PubChem CID	68664
ChemSpider	61918^Y
UNII	787AQ35GHR
ChEMBL	ChEMBL1076256^Y
CompTox Dashboard (EPA)	DTXSID2046206
Chemical and physical data
Formula	C₂₀H₂₀N₂O₂
Molar mass	320.392 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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Befuraline

Synthesis

See also

References