5-MeO-DiBF

{{short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

| verifiedrevid =

| IUPAC_name = N-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine

| image = 5-MeO-DiBF.svg

| width = 200

| image2 = 5-MeO-DiBF 3D BS.png

| width2 = 200

| tradename =

| pregnancy_category =

| legal_DE = NpSG

| legal_UK = Class A

| legal_US = ?

| routes_of_administration = ?

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number =none

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 98H5PQ3THV

| ATC_prefix =

| ATC_suffix =

| PubChem = 125276632

| ChemSpiderID_Ref =

| ChemSpiderID = 58191435

| StdInChI_Ref =

| StdInChI = 1S/C17H25NO2/c1-12(2)18(13(3)4)9-8-14-11-20-17-7-6-15(19-5)10-16(14)17/h6-7,10-13H,8-9H2,1-5H3

| StdInChIKey_Ref =

| StdInChIKey = NBFMSQBTYHYVKP-UHFFFAOYSA-N

| synonyms =

| C=17 | H=25 | N=1 | O=2

| smiles = COC1=CC=C(OC=C2CCN(C(C)C)C(C)C)C2=C1

}}

5-MeO-DiBF is a psychedelic{{Cite journal | vauthors = Casale JF, Hays PA | title = The Characterization of 2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine (5-MeO-BFE) and Differentiation from its N-Ethyl Analog | journal = Microgram Journal | volume = 9 | issue = 1 | pages = 39–45 | url = http://www.dea.gov/pr/microgram-journals/2012/mj9-1_39-45.pdf}} that has been sold online as a designer drug and was first definitively identified in December 2015 by a forensic laboratory in Slovenia.{{cite web | url = http://www.emcdda.europa.eu/system/files/publications/2880/TDAS16001ENN.pdf | publisher = European Monitoring Center for Drugs and Drug Addiction | title = Europol 2015 Annual Report on the implementation of Council Decision 2005/387/JHA }} It is thought to act as an agonist for the 5-HT_1A and 5-HT₂ family of serotonin receptors. It is related in structure to the psychedelic tryptamine derivative 5-MeO-DiPT, but with the indole nitrogen replaced by oxygen, making 5-MeO-DiBF a benzofuran derivative. It is several times less potent as a serotonin agonist than 5-MeO-DiPT and with relatively more activity at 5-HT_1A, but still shows strongest effects at the 5-HT₂ family of receptors.{{cite journal | vauthors = Tomaszewski Z, Johnson MP, Huang X, Nichols DE | title = Benzofuran bioisosteres of hallucinogenic tryptamines | journal = Journal of Medicinal Chemistry | volume = 35 | issue = 11 | pages = 2061–4 | date = May 1992 | pmid = 1534585 | doi = 10.1021/jm00089a017 }}{{cite journal | vauthors = McKenna DJ, Repke DB, Lo L, Peroutka SJ | title = Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes | journal = Neuropharmacology | volume = 29 | issue = 3 | pages = 193–8 | date = March 1990 | pmid = 2139186 | doi = 10.1016/0028-3908(90)90001-8 | s2cid = 24188017 | doi-access = free }}