:2CBFly-NBOMe

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| Watchedfields = changed

| verifiedrevid = 452171769

| ImageFile = 2CBFly-NBOMe.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 244

| ImageName = Kekulé, skeletal formula of 2CBFly-NBOMe

| ImageFile2 = 2CBFly-NBOMe-3D-balls.png

| PIN = 2-(8-Bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b′]difuran-4-yl)-N-[(2-methoxyphenyl)methyl]ethan-1-amine

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| Section1 = {{Chembox Identifiers

| Abbreviations = 2CBFly-NBOMe

| ChemSpiderID = 26234936

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| CASNo_Ref = {{cascite|correct|chemspider}}

| CASNo = 1335331-42-4

| PubChem = 57469208

| SMILES = COc1ccccc1CNCCc1c2CCOc2c(Br)c2CCOc12

| SMILES1 = COC1=C(CNCCC2=C3OCCC3=C(Br)C3=C2CCO3)C=CC=C1

| StdInChI = 1S/C20H22BrNO3/c1-23-17-5-3-2-4-13(17)12-22-9-6-14-15-7-10-25-20(15)18(21)16-8-11-24-19(14)16/h2-5,22H,6-12H2,1H3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CUFCITSPWAZWHS-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

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| Section2 = {{Chembox Properties

| C=20|H=22|Br=1|N=1|O=3

| MolarMass = 404.298 g/mol

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2CBFly-NBOMe (NBOMe-2C-B-FLY, Cimbi-31) is a drug of the phenethylamine, DOx, and FLY families. It was indirectly derived from the phenethylamine hallucinogen 2C-B, and related to benzodifurans like 2C-B-FLY and N-benzylphenethylamines like 25I-NBOMe. It was discovered in 2002,{{cite journal | vauthors = Elz S, Klass T, Heim R, Warnke U, Pertz HH |title= Development of highly potent partial agonists and chiral antagonists as tools for the study of 5-HT2A-receptor mediated function |journal= Naunyn-Schmiedeberg's Archives of Pharmacology |volume= 365 |issue= 1 Suppl|pages= R21–R40 |year= 2002|doi=10.1007/s00210-002-0604-4 }} and further researched by Ralf Heim at the Free University of Berlin,{{Cite thesis |type=PhD. |title=Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts |url=http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 |last=Heim |first=Ralf | name-list-style = vanc |year=2004 |publisher=Free University of Berlin }} and subsequently investigated in more detail by a team at Purdue University led by David E. Nichols.{{Cite thesis |type=PhD. |title=Towards a biophysical understanding of hallucinogen action |last=Braden |first=Michael Robert | name-list-style = vanc |year=2007 |publisher=Purdue University |id={{ProQuest|304838368}} }} It acts as a potent partial agonist for the 5-HT_2A serotonin receptor subtype.{{cite journal | vauthors = Silva ME, Heim R, Strasser A, Elz S, Dove S | title = Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor | journal = Journal of Computer-Aided Molecular Design | volume = 25 | issue = 1 | pages = 51–66 | date = January 2011 | pmid = 21088982 | doi = 10.1007/s10822-010-9400-2 | bibcode = 2011JCAMD..25...51S | s2cid = 3103050 | citeseerx = 10.1.1.688.2670 }}{{cite journal | vauthors = Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM | display-authors = 6 | title = Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers | journal = European Journal of Nuclear Medicine and Molecular Imaging | volume = 38 | issue = 4 | pages = 681–93 | date = April 2011 | pmid = 21174090 | doi = 10.1007/s00259-010-1686-8 | s2cid = 12467684 }}

{{Cite thesis |type=PhD. |title=Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain |url=http://bitnest.ca/external.php?id=%2518%253A3%25172%251BE%2524K%255BG%2521%2524%257D%2504%2504V |last=Hansen |first=Martin | name-list-style = vanc |year=2011 |publisher=University of Copenhagen |access-date=2012-11-02 |archive-url=https://web.archive.org/web/20131022035800/http://bitnest.ca/external.php?id=%2518%253A3%25172%251BE%2524K%255BG%2521%2524%257D%2504%2504V |archive-date=2013-10-22 |url-status=dead }}