2C-CN, also known as 4-cyano-2,5-dimethoxyphenethylamine, is a serotonin receptor modulator and possible serotonergic psychedelic of the phenethylamine and 2C families.
2C-CN was previously not known to have been tested in humans and it was unknown whether it produces psychedelic effects. According to Daniel Trachsel however, 2C-CN was inactive at a dose of 10mg orally, whereas a dose of 22mg orally possibly produced threshold effects.
2C-CN is a serotonin 5-HT<sub>2</sub> receptor partial to full agonist, including of the serotonin 5-HT<sub>2A</sub>, 5-HT<sub>2B</sub>, and 5-HT<sub>2C</sub> receptors. Its () values were 78âÂÂ503nM (73âÂÂ91%) at the serotonin 5-HT<sub>2A</sub> receptor, 650nM (82%) at the serotonin 5-HT<sub>2B</sub> receptor, and 140nM (101%) at the serotonin 5-HT<sub>2C</sub> receptor. The drug was 10-fold or more less potent as a serotonin 5-HT<sub>2A</sub> receptor agonist than other notable 2C psychedelics including 2C-B, 2C-D, 2C-T, 2C-P, and 2C-T-7.
The chemical synthesis of 2C-CN has been described.
2C-CN is the 2C parent compound of potent serotonin 5-HT<sub>2A</sub> receptor agonists of the 25-NB family including 25CN-NBOH, 25CN-NBOMe, 25CN-NBF, and 25CN-NBMD, among others. 25CN-NBOH is notable in being one of the most selective serotonin 5-HT<sub>2A</sub> receptor agonists known. In addition, 25-NB derivatives of 2C-CN are known that act as ò-arrestin-biased serotonin 5-HT<sub>2A</sub> receptor agonists.
2C-CN was first described in the scientific literature by 1984. It was briefly mentioned by Alexander Shulgin in his books PiHKAL (Phenethylamines I Have Known and Loved) (1991) and ' (2011). Daniel Trachsel described 2C-CN's preliminary properties and effects in humans in 2013. The drug's pharmacology was elucidated in the mid-2020s.
2C-CN is a controlled substance in Canada under phenethylamine blanket-ban language.
2C-CN is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.