2C-CN

2C-CN, also known as 4-cyano-2,5-dimethoxyphenethylamine, is a chemical compound of the phenethylamine and 2C families.^{[1][2][3][4][5][6]} It was not known to have been tested in humans and it is unknown whether it produces psychedelic effects.^[1][2] According to Daniel Trachsel however, 2C-CN was inactive at an oral dose of 10 mg, whereas an oral dose of 22 mg possibly produced threshold effects.^[7]

2C-CN

Clinical data
Other names	25CN; 2,5-Dimethoxy-4-cyanophenethylamine; 4-Cyano-2,5-dimethoxyphenethylamine
Identifiers
IUPAC name 4-(2-aminoethyl)-2,5-dimethoxybenzonitrile
CAS Number	88441-07-0
PubChem CID	57474247
ChemSpider	28690053
UNII	68O9X0114E
CompTox Dashboard (EPA)	DTXSID00726819
Chemical and physical data
Formula	C11H14N2O2
Molar mass	206.245 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C=C1CCN)OC)C#N
InChI InChI=1S/C11H14N2O2/c1-14-10-6-9(7-13)11(15-2)5-8(10)3-4-12/h5-6H,3-4,12H2,1-2H3 Key:OGWCKYKYGQORLF-UHFFFAOYSA-N

The drug is the 2C parent compound of potent serotonin 5-HT_2A receptor agonists of the 25-NB family including 25CN-NBOH, 25CN-NBOMe, 25CN-NBF, and 25CN-NBMD, among others.^{[8][9][10][6][11][12]} 25CN-NBOH is notable in being one of the most selective serotonin 5-HT_2A receptor agonists known.^[8][11] In addition, 25-NB derivatives of 2C-CN are known that act as β-arrestin-biased serotonin 5-HT_2A receptor agonists.^[6]

2C-CN was first described in the scientific literature by 1984.^[3] 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).^[1][2]

See also

• 2C (psychedelics)
• DOCN
• 2C-N