2C-Ph, or 2C-Phenyl, also known as 2C-BI-1 or as 2,5-dimethoxy-4-phenylphenethylamine, is a serotonin receptor modulator of the phenethylamine and 2C families that was developed by Daniel Trachsel and David E. Nichols and colleagues.
The drug's affinity (K<sub>i</sub>) for the rat serotonin 5-HT<sub>2A</sub> receptor was 778nM. It was said to be an antagonist of this receptor. In a subsequent study, 2C-Ph was a weak partial agonist of the human serotonin 5-HT<sub>2A</sub> receptor (K<sub>i</sub> = 630nM, = 1,596nM, = 23%). The drug also shows affinity for the serotonin 5-HT<sub>1A</sub>, 5-HT<sub>2B</sub>, and 5-HT<sub>2C</sub> receptors, but did not activate the serotonin 5-HT<sub>2B</sub> receptor. In addition, it interacted with other monoamine receptors, with the monoamine transporters, and was a potent and high-efficacy partial agonist of the human trace amine-associated receptor 1 (TAAR1) ( = 580nM, = 82%).
Besides 2C-Ph itself, a variety of derivatives of 2C-Ph with substituents on the 4-position phenyl ring have been synthesized and studied by Trachsel and colleagues. These drugs, inclusive of 2C-Ph, have been denoted 2C-BI-1 to 2C-BI-12. 2C-BI-4 (the 2â²-trifluoromethyl derivative), 2C-BI-8 (the 4â²-methoxy derivative), and 2C-BI-12 (the 3â²,4â²-dimethoxy derivative) are agonists of the human serotonin 5-HT<sub>2A</sub> receptor with higher efficacy than 2C-Ph ( = 37âÂÂ2,408nM, = 38âÂÂ44%). The effects of 2C-Ph and its derivatives in humans are unknown. However, 2C-BI-8 and 2C-BI-12, the most potent agonists, in particular might have the potential for psychedelic effects.
2C-Ph was first described in the scientific literature, by Trachsel and Nichols and colleagues, in 2009. It is a controlled substance in Canada under phenethylamine blanket-ban language.