2,5-Dimethoxy-4-cyanoamphetamine

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DOCN
Clinical data
Other namesDOCN; 2,5-Dimethoxy-4-cyanoamphetamine; 4-Cyano-2,5-dimethoxyamphetamine
Drug classSerotonergic agent; Serotonin 5-HT2 receptor modulator
ATC code
  • None
Identifiers
  • 4-(2-aminopropyl)-2,5-dimethoxybenzonitrile
CAS Number
PubChem CID
ChemSpider
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC12H16N2O2
Molar mass220.272 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=C(C=C1OC)C#N)OC)N
  • 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

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]

Use and effects

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

Interactions

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

Pharmacology

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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-HT2A receptor over the serotonin 5-HT2C 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-HT2A receptor agonists discovered to date.[5][7]

Chemistry

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Analogues

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

History

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

Society and culture

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

See also

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References

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