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{{Short description|Psychoactive drug of the piperazine chemical class}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
{{Drugbox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 401815090
| verifiedrevid =
| IUPAC_name = 1-benzofuran-2-yl(4-benzylpiperazin-1-yl)methanone
| IUPAC_name = 1-benzofuran-2-yl(4-benzylpiperazin-1-yl)methanone
| image = Befuraline.png
| image = Befuraline.
<!--Clinical data-->
⚫
| CASNo_Ref = {{cascite|correct|??}}
| tradename =
⚫
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫
| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
<!--Identifiers-->
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| = {{cascite|correct|??}}
⚫
| CAS_number = 41717-30-0
⚫
| CAS_supplemental = {{CAS|41716-84-1}}
⚫
| ATC_prefix = none
⚫
| PubChem = 68664
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| ChemSpiderID=61918
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 787AQ35GHR
| UNII = 787AQ35GHR
⚫
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| InChI = 1/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
⚫
| ChEMBL = 1076256
| InChIKey = SRIJFPBZWUFLFD-UHFFFAOYAZ
<!--Chemical data-->
⚫
| C=20 | H=20
| N=2 | O=2
| smiles = O=C(N1CCN(CC1)CC2=CC=CC=C2)C3=CC4=C(C=CC=C4)O3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SRIJFPBZWUFLFD-UHFFFAOYSA-N
| StdInChIKey = SRIJFPBZWUFLFD-UHFFFAOYSA-N
⚫
| CAS_number = 41717-30-0
⚫
| CAS_supplemental = {{CAS|41716-84-1}} ([[hydrochloride|HCl]])
⚫
| ATC_prefix = none
| ATC_suffix =
| ATC_supplemental =
⚫
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫
| ChEMBL = 1076256
⚫
| PubChem = 68664
| DrugBank =
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫
| ChemSpiderID=61918
⚫
| C=20 | H=20 | N=2 | O=2
| molecular_weight = 320.385 g/mol
| smiles = O=C(c2oc1ccccc1c2)N4CCN(Cc3ccccc3)CC4
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
⚫
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category=
⚫
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| routes_of_administration =
}}
}}


'''Befuraline''' ('''DIV-154''') is a [[psychoactive drug]] and member of the [[piperazine]] [[chemical class]] which was [[drug development|developed]] in [[Germany]] in the [[1970]]s.<ref>Boksay IJ, Popendiker K, Weber RO, Soder A. Synthesis and pharmacological activity of befuraline (N-benzo[b]furan-2-ylcarbonyl-N'-benzylpiperazine), a new antidepressant compound. Arzneimittel-Forschung. 1979;29(2):193-204.</ref> Befuraline has [[stimulant]] and [[antidepressant]] effects and has seen some use in Germany and [[France]], although it has never become widely used.<ref> Gastpar M, Gastpar G, Gilsdorf U. Befuraline, its safety and efficacy in depressed inpatients. Pharmacopsychiatry. 1985 Nov;18(6):351-5.</ref> Befuraline's active [[metabolite]] [[benzylpiperazine]] is responsible for its effects.
'''Befuraline''' ('''DIV-154''') is a [[psychoactive drug]] and member of the [[piperazine]] [[chemical class]] which was [[drug development|developed]] in [[Germany]] in the .<ref>Boksay IJ, Popendiker K, Weber RO, A Synthesis and pharmacological activity of befuraline (N-benzo[b]furan-2-ylcarbonyl-N'-benzylpiperazine), a new antidepressant compound Arzneimittel-Forschung 292</ref> Befuraline has [[stimulant]] and [[antidepressant]] effects and has seen some use in Germany and [[France]], although it has never become widely used.<ref> Gastpar M, Gastpar G, Gilsdorf U Befuraline, its safety and efficacy in depressed inpatients Pharmacopsychiatry 186.</ref> Befuraline's active [[metabolite]] [[benzylpiperazine]] is its effects.
==Synthesis==

[[File:Befuraline synthesis.svg|thumb|center|500px|Synthesis:<ref name="pmid582130"/> Patent:<ref>DE2157424 idem Rolf-Ortwin Weber, Alfons Soder, Istvan Boksay, {{US patent|4374990}} (1980 to Hoechst Aktiengesellschaft).</ref>]]
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==
==See also==
* [[Substituted piperazine]]
* [[Fipexide]]
* [[Fipexide]]
* [[Piberaline]]
* [[Piberaline]]
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{{Antidepressants}}
{{Antidepressants}}
{{Stimulants}}
{{Stimulants}}
{{Adrenergics}}
{{Dopaminergics}}
{{Serotonergics}}
{{Piperazines}}
{{Piperazines}}


[[Category:Anthelmintics]]
[[Category:Anthelmintics]]
[[Category:Piperazines]]
[[Category:Piperazines]]
[[Category:Amides]]
[[Category:]]
[[Category:Benzofurans]]
[[Category:]]




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