2C-Ph

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| class = Serotonin receptor modulator

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| PubChem = 57474287

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| synonyms = 2C-BI-1; 2,5-Dimethoxy-4-phenylphenethylamine; 4-Phenyl-2,5-dimethoxyphenethylamine

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

| C=16 | H=19 | N=1 | O=2

| SMILES = NCCc1cc(OC)c(cc1OC)c1ccccc1

| StdInChI = 1S/C16H19NO2/c1-18-15-11-14(12-6-4-3-5-7-12)16(19-2)10-13(15)8-9-17/h3-7,10-11H,8-9,17H2,1-2H3

| StdInChIKey = RMMCNNHGPNUXOX-UHFFFAOYSA-N

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2C-Ph, also known as 2C-BI-1 or as 2,5-dimethoxy-4-phenylphenethylamine, is a serotonin receptor modulator of the phenethylamine and 2C families that was developed by Daniel Trachsel and David E. Nichols and colleagues.{{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 }}

The drug's affinity (K_i) for the rat serotonin 5-HT_2A receptor was 778{{nbsp}}nM. It was said to be an antagonist of this receptor. In a subsequent study, 2C-Ph was a weak partial agonist of the human serotonin 5-HT_2A receptor (K_i = 630{{nbsp}}nM, {{Abbrlink|EC₅₀|half-maximal effective concentration}} = 1,596{{nbsp}}nM, {{Abbrlink|E_max|maximal efficacy}} = 23%). The drug also shows affinity for the serotonin 5-HT_1A, 5-HT_2B, and 5-HT_2C receptors, but did not activate the serotonin 5-HT_2B receptor. In addition, it interacted with other monoamine receptors, with the monoamine transporters, and was a potent and high-efficacy partial agonist of the human trace amine-associated receptor 1 (TAAR1) ({{Abbr|EC₅₀|half-maximal effective concentration}} = 580{{nbsp}}nM, {{Abbr|E_max|maximal efficacy}} = 82%).

Besides 2C-Ph itself, a variety of derivatives of 2C-Ph with substituents on the 4-position phenyl ring have been synthesized and studied by Trachsel and colleagues. These drugs, inclusive of 2C-Ph, have been denoted 2C-BI-1 to 2C-BI-12. 2C-BI-4 (the 2′-trifluoromethyl derivative), 2C-BI-8 (the 4′-methoxy derivative), and 2C-BI-12 (the 3′,4′-dimethoxy derivative) are agonists of the human serotonin 5-HT_2A receptor with higher efficacy than 2C-Ph ({{Abbr|EC₅₀|half-maximal effective concentration}} = 37–2,408{{nbsp}}nM, {{Abbr|E_max|maximal efficacy}} = 38–44%). The effects of 2C-Ph and its derivatives in humans are unknown. However, 2C-BI-8 and 2C-BI-12, the most potent agonists, in particular might have the potential for psychedelic effects.

2C-Ph was first described in the scientific literature, by Trachsel and Nichols and colleagues, in 2009.