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2C-tBu

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Pharmaceutical compound
2C-tBu
Clinical data
Other names2,5-Dimethoxy-4-tert-butylphenethylamine; 4-tert-Butyl-2,5-dimethoxyphenethylamine; 2C-TBU; 2C-t-Bu
Drug classSerotonin receptor agonist;Serotonergic psychedelic;Hallucinogen
Identifiers
  • 2-(4-tert-butyl-2,5-dimethoxyphenyl)ethanamine
PubChemCID
ChemSpider
Chemical and physical data
FormulaC14H23NO2
Molar mass237.343 g·mol−1
3D model (JSmol)
  • CC(C)(C)C1=C(C=C(C(=C1)OC)CCN)OC
  • InChI=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
  • Key:MHNFTGKRRUDUST-UHFFFAOYSA-N

2C-tBu, also known as2,5-dimethoxy-4-tert-butylphenethylamine, is aserotonin receptoragonist and putativeserotonergic psychedelic of thephenethylamine and2C families.[1][2] It is apotentserotonin5-HT2A receptor agonist (Ki = 9.9–35 nM,EC50Tooltip half-maximal effective concentration = 4.2 nM) and also binds to the serotonin5-HT2C receptor (Ki = 7–24 nM).[1][2] The drug produces a robusthead-twitch response, a behavioral proxy of psychedelic effects, in rodents.[2] The active dosage in humans is >5 mg perDaniel Trachsel and itsduration is unknown.[1] Initial tests with 7 mg and 10 mg (as 5 mg plus 5 mg 2 hours apart) produced no psychedelic effects in humans, but instead induced a pronounced and long-lastingtiredness.[1] It was hypothesized that 2C-tBu might be a serotonin 5-HT2A receptorantagonist and might thereby behypnotic,[1] but it was instead shown to be an agonist in subsequent studies.[2]

See also

[edit]

References

[edit]
  1. ^abcdeTrachsel D, Lehmann D, Enzensperger C (2013).Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German). Solothurn: Nachtschatten-Verlag. pp. 766–767, 771, 901.ISBN 978-3-03788-700-4.OCLC 858805226. Retrieved29 January 2025.
  2. ^abcdVarty GB, Canal CE, Mueller TA, Hartsel JA, Tyagi R, Avery K, et al. (April 2024). "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 of Medicinal Chemistry.67 (8):6144–6188.doi:10.1021/acs.jmedchem.3c01961.PMID 38593423.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.

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