2C-BI-8

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]

2C-BI-8

Clinical data
Other names	2,5-Dimethoxy-4-(4-methoxyphenyl)phenethylamine; 2C-(4-MeO-Ph); 4′-Methoxy-2C-Ph
Drug class	Serotonin receptor modulator
Identifiers
IUPAC name 2-(2,4′,5-trimethoxy[1,1′-biphenyl]-4-yl)ethan-1-amine
Chemical and physical data
Formula	C17H21NO3
Molar mass	287.359 g·mol−1
3D model (JSmol)	Interactive image
SMILES NCCc1cc(OC)c(cc1OC)c1ccc(cc1)OC
InChI 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

The drug binds to and/or activates the serotonin 5-HT₂ receptors.^[1][2][3] At the human serotonin 5-HT_2A receptor, its affinity (K_i) is 19 nM, activational potency (EC₅₀Tooltip half-maximal effective concentration) is 37 nM, and intrinsic activity (E_maxTooltip 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]

See also

• Biscaline
• 2C-T-27
• 2C-T-33
• 4-PhPr-2,5-DMA (DOPP/DOPhPr)
• 2,5-Dimethoxy-4-benzylamphetamine (DOBz)