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1-Methylpsilocin

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1-Methylpsilocin
Identifiers
  • 1-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18N2O
Molar mass218.294 g/mol g·mol−1
3D model (JSmol)
  • 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

  1. ^ Sard, H; Kumaran, G; Morency, C; Roth, B. L.; Toth, B. A.; He, P; Shuster, L (2005). "SAR of psilocybin analogs: Discovery of a selective 5-HT 2C agonist". Bioorganic & Medicinal Chemistry Letters. 15 (20): 4555–9. doi:10.1016/j.bmcl.2005.06.104. PMID 16061378.
  2. ^ Sewell, R. A.; Halpern, J. H.; Pope Jr, H. G. (2006). "Response of cluster headache to psilocybin and LSD". Neurology. 66 (12): 1920–2. doi:10.1212/01.wnl.0000219761.05466.43. PMID 16801660.
  3. ^ Halberstadt, A. L.; Koedood, L; Powell, S. B.; Geyer, M. A. (2011). "Differential contributions of serotonin receptors to the behavioral effects of indoleamine hallucinogens in mice". Journal of Psychopharmacology. 25 (11): 1548–61. doi:10.1177/0269881110388326. PMC 3531560. PMID 21148021.


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