2C-tBu

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| image = 2C-TBU structure.png

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| class = Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen

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| PubChem = 117347542

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| ChemSpiderID = 76370331

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| synonyms = 2,5-Dimethoxy-4-tert-butylphenethylamine; 4-tert-Butyl-2,5-dimethoxyphenethylamine; 2C-TBU; 2C-t-Bu

| IUPAC_name = 2-(4-tert-butyl-2,5-dimethoxyphenyl)ethanamine

| C=14 | H=23 | N=1 | O=2

| SMILES = CC(C)(C)C1=C(C=C(C(=C1)OC)CCN)OC

| StdInChI = 1S/C14H23NO2/c1-14(2,3)11-9-12(16-4)10(6-7-15)8-13(11)17-5/h8-9H,6-7,15H2,1-5H3

| StdInChIKey = MHNFTGKRRUDUST-UHFFFAOYSA-N

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2C-tBu, or 2C-t-Bu, also known as 4-tert-butyl-2,5-dimethoxyphenethylamine, is a serotonin receptor agonist and putative serotonergic psychedelic 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 | pages=766–767,771,901 }}{{cite journal | vauthors = Varty GB, Canal CE, Mueller TA, Hartsel JA, Tyagi R, Avery K, Morgan ME, Reichelt AC, Pathare P, Stang E, Palfreyman MG, Nivorozhkin A | title = Synthesis and Structure-Activity Relationships of 2,5-Dimethoxy-4-Substituted Phenethylamines and the Discovery of CYB210010: A Potent, Orally Bioavailable and Long-Acting Serotonin 5-HT₂ Receptor Agonist | journal = Journal of Medicinal Chemistry | volume = 67 | issue = 8 | pages = 6144–6188 | date = April 2024 | pmid = 38593423 | doi = 10.1021/acs.jmedchem.3c01961 | quote = The 4-tert-butyl group was considered as a spot for potential hydroxylation by cytochrome P450s to discover analogs with short-lasting effects. However, 2C-t-Bu was a potent agonist at the 5-HT2A receptor (Ki = 9.9 nM, EC50 = 4.2 nM) and elicited a robust HTR (Supporting Information, Table S1), providing in vivo evidence that the tert-butyl group is not rapidly metabolized to an inactive compound in mice, despite predictions. }}

It is a potent serotonin 5-HT_2A receptor agonist (K_i = 9.9–35{{nbsp}}nM, {{Abbrlink|EC₅₀|half-maximal effective concentration}} = 4.2{{nbsp}}nM) and also binds to the serotonin 5-HT_2C receptor (K_i = 7–24{{nbsp}}nM). The drug produces a robust head-twitch response, a behavioral proxy of psychedelic effects, in rodents. It also produces hyperlocomotion in rodents.

The active dosage in humans is >5{{nbsp}}mg per Daniel Trachsel and its duration is unknown. Initial tests with 7{{nbsp}}mg and with 10{{nbsp}}mg (as 5{{nbsp}}mg plus 5{{nbsp}}mg 2{{nbsp}}hours apart) produced no psychedelic effects in humans, but instead induced a pronounced and long-lasting tiredness.

It was hypothesized that 2C-tBu might be a serotonin 5-HT_2A receptor antagonist and might thereby be hypnotic, but it was instead shown to be an agonist in subsequent studies.