2C-CN

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]}

2C-CN

Clinical data
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
ATC code	None
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

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

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

2C-CN is a serotonin 5-HT₂ receptor partial to full agonist, including of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[4][9] Its EC₅₀Tooltip half-maximal effective concentration (E_maxTooltip maximal efficacy) values were 78–503 nM (73–91%) at the serotonin 5-HT_2A receptor, 650 nM (82%) at the serotonin 5-HT_2B receptor, and 140 nM (101%) at the serotonin 5-HT_2C receptor.^[4][9] The drug was 10-fold or more less potent as a serotonin 5-HT_2A 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-HT_2A 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-HT_2A receptor agonists known.^[10][13] In addition, 25-NB derivatives of 2C-CN are known that act as β-arrestin-biased serotonin 5-HT_2A 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]

See also

• 2C (psychedelics)
• DOCN
• 2C-N
• TGF-8027