1-Methylpsilocin

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1-Methylpsilocin
1-Methylpsilocin structure.png
Systematic (IUPAC) name
1-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole
Identifiers
CAS Number 1465-16-3 N
PubChem CID: 44404883
ChemSpider 21686519
Chemical data
Formula C13H18N2O
Molecular mass 218.294 g/mol
  • CN(C)CCc(cn1C)c2c1cccc2O
  • InChI=1S/C13H18N2O/c1-14(2)8-7-10-9-15(3)11-5-4-6-12(16)13(10)11/h4-6,9,16H,7-8H2,1-3H3
  • Key:MZZRFEIDRWKTKJ-UHFFFAOYSA-N

1-Methylpsilocin is a tryptamine derivative which acts as a selective agonist for the 5-HT2C receptor (IC50 of 12 nM, vs 633 nM at 5-HT2A), and an inverse agonist at 5-HT2B (Ki of 38 nM). While 1-methylpsilocin does have higher affinity for 5-HT2C than 5-HT2A, it does produces a head-twitch response in mice that is dependent on 5-HT2A, so it is not entirely free of effects on 5-HT2A in vivo. In contrast to psilocin, 1-methylpsilocin did not activate 5-HT1A receptors in mice. 1-Methylpsilocin has been investigated for applications such as treatment of glaucoma, OCD, and cluster headaches, as these conditions are amenable to treatment with psychedelic drugs but are not generally treated with such agents due to the undesirable hallucinogenic side effects they produce. 1-Methylpsilocin therefore represents a potential alternative treatment to psilocin that may be less likely to produce hallucinogenic effects.[1][2][3]

See also

References

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