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. "The treatment of the 2C-B phthalimide described above, with cuprous cyanide rather than cuprous chloride, gave rise to the cyano analog which, on hydrolysis with hydrazine, yielded 2,5-dimethoxy-4-cyanophenethylamine (2C-CN). Hydrolysis of this with hot, strong base gave the corresponding acid, 2,5-dimethoxy-4-carboxyphenethylamine, 2C-COOH. No evaluation of either of these compounds has been made in the human animal, as far as I know."
Use and effects 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.
Interactions
Pharmacology Pharmacodynamics 2C-CN is a serotonin 5-HT2 receptor partial to full agonist, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. Its () values were 78–503nM (73–91%) at the serotonin 5-HT2A receptor, 650nM (82%) at the serotonin 5-HT2B receptor, and 140nM (101%) at the serotonin 5-HT2C receptor. The drug was 10-fold or more less potent as a serotonin 5-HT2A receptor agonist than other notable 2C psychedelics including 2C-B, 2C-D, 2C-T, 2C-P, and 2C-T-7.
Chemistry Synthesis The chemical synthesis of 2C-CN has been described.
Derivatives 2C-CN is the 2C parent compound of potent serotonin 5-HT2A 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-HT2A receptor agonists known. In addition, 25-NB derivatives of 2C-CN are known that act as β-arrestin-biased serotonin 5-HT2A receptor agonists.
History 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 The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds (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.
Society and culture Legal status Canada 2C-CN is a controlled substance in Canada under phenethylamine blanket-ban language.
United States 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.
See also 2C (psychedelics) DOCN 2C-N TGF-8027
References
External links 2C-CN - Isomer Design