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2C-BI-8

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2C-BI-8
Clinical data
Other names2,5-Dimethoxy-4-(4-methoxyphenyl)phenethylamine; 2C-(4-MeO-Ph); 4′-Methoxy-2C-Ph
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 2-(2,4′,5-trimethoxy[1,1′-biphenyl]-4-yl)ethan-1-amine
Chemical and physical data
FormulaC17H21NO3
Molar mass287.359 g·mol−1
3D model (JSmol)
  • NCCc1cc(OC)c(cc1OC)c1ccc(cc1)OC
  • InChI=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
  • Key:ZALWHJKGZWNFNR-UHFFFAOYSA-N

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.[1][2][3] It is the derivative of 2C-Ph (2C-BI-1) with a methoxy group at the 4 position of the added phenyl ring.[1][3]

The drug binds to and/or activates the serotonin 5-HT2 receptors.[1][2][3] At the human serotonin 5-HT2A receptor, its affinity (Ki) is 19 nM, activational potency (EC50Tooltip half-maximal effective concentration) is 37 nM, and intrinsic activity (EmaxTooltip maximal efficacy) is 40%.[3] These were among the most potent and efficacious in a series of evaluated 2C-Ph derivatives (2C-BI compounds) that included 2C-BI-8.[3] 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.[3] The drug also interacts with certain other monoamine receptors and has been assessed at the monoamine transporters.[3] It may have the potential to produce psychedelic effects in humans.[1][3]

2C-BI-8 was first described in the scientific literature by Daniel Trachsel and David E. Nichols and colleagues in 2009.[1][2][3] It is a controlled substance in Canada under phenethylamine blanket-ban language.[4]

See also

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References

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  1. 1 2 3 4 5 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. p. 806. ISBN 978-3-03788-700-4. OCLC 858805226. Retrieved 29 January 2025.
  2. 1 2 3 Trachsel D, Nichols DE, Kidd S, Hadorn M, Baumberger F (May 2009). "4-aryl-substituted 2,5-dimethoxyphenethylamines: synthesis and serotonin 5-HT(2A) receptor affinities". Chemistry & Biodiversity. 6 (5): 692–704. doi:10.1002/cbdv.200800235. PMID 19479848.
  3. 1 2 3 4 5 6 7 8 9 Luethi D, Widmer R, Trachsel D, Hoener MC, Liechti ME (July 2019). "Monoamine receptor interaction profiles of 4-aryl-substituted 2,5-dimethoxyphenethylamines (2C-BI derivatives)". European Journal of Pharmacology. 855: 103–111. doi:10.1016/j.ejphar.2019.05.014. PMID 31063768.
  4. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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