2C-BI-8

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| class = Serotonin receptor modulator

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| synonyms = 2,5-Dimethoxy-4-(4-methoxyphenyl)phenethylamine; 2C-(4-MeO-Ph); 4′-Methoxy-2C-Ph

| IUPAC_name = 2-(2,4′,5-trimethoxy[1,1′-biphenyl]-4-yl)ethan-1-amine

| C=17 | H=21 | N=1 | O=3

| SMILES = NCCc1cc(OC)c(cc1OC)c1ccc(cc1)OC

| StdInChI = 1S/C17H21NO3/c1-19-14-6-4-12(5-7-14)15-11-16(20-2)13(8-9-18)10-17(15)21-3/h4-7,10-11H,8-9,18H2,1-3H3

| StdInChIKey = ZALWHJKGZWNFNR-UHFFFAOYSA-N

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2C-BI-8, also known as 2,5-dimethoxy-4-(4-methoxyphenyl)phenethylamine or as 4′-methoxy-2C-Ph, is a serotonin receptor agonist of the phenethylamine and 2C families.{{cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | title=Phenethylamine: von der Struktur zur Funktion | trans-title = Phenethylamines: From Structure to Function | publisher=Nachtschatten-Verlag | location=Solothurn | series=Nachtschatten-Science | year=2013 | isbn=978-3-03788-700-4 | oclc=858805226 | url=https://books.google.com/books?id=-Us1kgEACAAJ | language=de | access-date=29 January 2025 | page=806 }}{{cite journal | vauthors = Trachsel D, Nichols DE, Kidd S, Hadorn M, Baumberger F | title = 4-aryl-substituted 2,5-dimethoxyphenethylamines: synthesis and serotonin 5-HT(2A) receptor affinities | journal = Chemistry & Biodiversity | volume = 6 | issue = 5 | pages = 692–704 | date = May 2009 | pmid = 19479848 | doi = 10.1002/cbdv.200800235 }}{{cite journal | vauthors = Luethi D, Widmer R, Trachsel D, Hoener MC, Liechti ME | title = Monoamine receptor interaction profiles of 4-aryl-substituted 2,5-dimethoxyphenethylamines (2C-BI derivatives) | journal = European Journal of Pharmacology | volume = 855 | issue = | pages = 103–111 | date = July 2019 | pmid = 31063768 | doi = 10.1016/j.ejphar.2019.05.014 }} It is the derivative of 2C-Ph (2C-BI-1) with a methoxy group at the 4 position of the added phenyl ring.

The drug binds to and/or activates the serotonin 5-HT₂ receptors. At the human serotonin 5-HT_2A receptor, its affinity (K_i) is 19{{nbsp}}nM, activational potency ({{Abbrlink|EC₅₀|half-maximal effective concentration}}) is 37{{nbsp}}nM, and intrinsic activity ({{Abbrlink|E_max|maximal efficacy}}) is 40%. These were among the most potent and efficacious in a series of evaluated 2C-Ph derivatives (2C-BI compounds) that included 2C-BI-8. However, 2C-BI-8's activational potency was about 18-fold lower than that of 2C-B and its efficacy was less than half of that of 2C-B. The drug also interacts with certain other monoamine receptors and has been assessed at the monoamine transporters. It may have the potential to produce psychedelic effects in humans.

2C-BI-8 was first described in the scientific literature by Daniel Trachsel and David E. Nichols and colleagues in 2009.