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2C-tBu

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2C-tBu
2C-TBU structure.png
Clinical data
Other names2,5-Dimethoxy-4-tert-butylphenethylamine; 4-tert-Butyl-2,5-dimethoxyphenethylamine; 2C-TBU; 2C-t-Bu
Drug class Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 2-(4-tert-butyl-2,5-dimethoxyphenyl)ethanamine
PubChem CID
ChemSpider
Chemical and physical data
Formula C14H23NO2
Molar mass 237.343 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, 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. [1] [2]

Contents

Use and effects

The active dose of 2C-tBu in humans is >5 mg orally per Daniel Trachsel and its duration is unknown. [1] Initial tests with 7 mg and with 10 mg (as 5 mg plus 5 mg 2 hours apart) orally produced no psychedelic effects in humans, but instead induced a pronounced and long-lasting tiredness. [1] It was hypothesized by Daniel Trachsel and colleagues that 2C-tBu might be a serotonin 5-HT2A receptor antagonist and might thereby be hypnotic, [1] but it was instead shown to be an agonist in subsequent studies. [2]

Interactions

Pharmacology

Pharmacodynamics

2C-tBu is a potent serotonin 5-HT2A receptor agonist (Ki = 9.9–35 nM, EC50 Tooltip half-maximal effective concentration = 4.2 nM) and also binds to the serotonin 5-HT2C receptor (Ki = 7–24 nM). [1] [2] The drug produces a robust head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [2] It also produces hyperlocomotion in rodents. [2]

Chemistry

Analogues

Analogues of 2C-tBu include 2C-Bu, 2C-iBu, 2C-sBu, and DOTB, among others. [1]

History

2C-tBu was first described in the scientific literature by Daniel Trachsel and colleagues in 2013. [1]

Society and culture

Canada

2C-tBu is a controlled substance in Canada under phenethylamine blanket-ban language. [3]

See also

References

  1. 1 2 3 4 5 6 7 Trachsel 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 . Retrieved 29 January 2025.
  2. 1 2 3 4 5 Varty 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.
  3. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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