2,5-Dimethoxy-4-cyanoamphetamine

2,5-Dimethoxy-4-cyanoamphetamine (DOCN) is a serotonergic drug of the phenethylamine, amphetamine, and DOx families.^[1][2][3] It is a DOx derivative with a cyano group (–C≡N) at the 4 position of the molecule.^[1][2][3]

DOCN

Clinical data
Other names	DOCN; 2,5-Dimethoxy-4-cyanoamphetamine; 4-Cyano-2,5-dimethoxyamphetamine
Drug class	Serotonergic agent; Serotonin 5-HT2 receptor modulator
ATC code	None
Identifiers
IUPAC name 4-(2-aminopropyl)-2,5-dimethoxybenzonitrile
CAS Number	125903-74-4
PubChem CID	23900148
ChemSpider	23108720
ChEMBL	ChEMBL8336
CompTox Dashboard (EPA)	DTXSID80635930
Chemical and physical data
Formula	C12H16N2O2
Molar mass	220.272 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC(=C(C=C1OC)C#N)OC)N
InChI InChI=1S/C12H16N2O2/c1-8(14)4-9-5-12(16-3)10(7-13)6-11(9)15-2/h5-6,8H,4,14H2,1-3H3 Key:ULNMEZQBQBLXMC-UHFFFAOYSA-N

Use and effects

The effects of DOCN in humans and whether it is a psychedelic are unknown.^[1]

Interactions

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

Pharmacology

DON shows much lower affinities for the serotonin 5-HT₂ receptors than other DOx drugs.^[4][2][3] However, DOCN also showed by far the greatest degree of selectivity for the serotonin 5-HT_2A receptor over the serotonin 5-HT_2C receptor (22-fold) of any other assessed DOx drug.^[5][6][2] Applying this strategy (i.e., cyano substitution) to the 25-NB series resulted in the discovery of 25CN-NBOH, one of the most selective serotonin 5-HT_2A receptor agonists discovered to date.^[5][7]

Chemistry

Analogues

Related drugs include DON, 2C-N, DOA, 2C-CN, 25CN-NBOH, and 25CN-NBOMe.^{[8][9][3][10]}

History

DOCN was first described in the scientific literature by Richard Glennon and colleagues by 1989.^[9][3]

Society and culture

Legal status

DOCN is not a controlled substance in the United States as of 2011.^[1]

See also

• DOx (psychedelics)
• 2C-N
• 2C-CN
• 25CN-NBOH
• 25CN-NBOMe