2C-CN
Pharmaceutical compound
From Wikipedia, the free encyclopedia
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.[2][3][4][5][6][7][8]
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| Other names | 25CN; 2,5-Dimethoxy-4-cyanophenethylamine; 4-Cyano-2,5-dimethoxyphenethylamine |
| Routes of administration | Oral[1] |
| Drug class | Serotonin receptor modulator; Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Possible serotonergic psychedelic or hallucinogen |
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| Duration of action | Unknown[1] |
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| Formula | C11H14N2O2 |
| Molar mass | 206.245 g·mol−1 |
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Use and effects
2C-CN was previously not known to have been tested in humans and it was unknown whether it produces psychedelic effects.[2][3] According to Daniel Trachsel however, 2C-CN was inactive at a dose of 10 mg orally, whereas a dose of 22 mg orally possibly produced threshold effects.[1]
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.[4][9] Its EC50 (Emax) values were 78–503 nM (73–91%) at the serotonin 5-HT2A receptor, 650 nM (82%) at the serotonin 5-HT2B receptor, and 140 nM (101%) at the serotonin 5-HT2C receptor.[4][9] 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.[9][4]
Chemistry
Synthesis
The chemical synthesis of 2C-CN has been described.[9][5]
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.[10][11][12][8][13][14] 25CN-NBOH is notable in being one of the most selective serotonin 5-HT2A receptor agonists known.[10][13] In addition, 25-NB derivatives of 2C-CN are known that act as β-arrestin-biased serotonin 5-HT2A receptor agonists.[8]
History
2C-CN was first described in the scientific literature by 1984.[5] 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).[2][3] Daniel Trachsel described 2C-CN's preliminary properties and effects in humans in 2013.[1] The drug's pharmacology was elucidated in the mid-2020s.[9][4]
Society and culture
Legal status
Canada
2C-CN is a controlled substance in Canada under phenethylamine blanket-ban language.[15]
United States
2C-CN is not an explicitly controlled substance in the United States.[16] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.