1-Methylpsilocin

1-Methylpsilocin
Identifiers
IUPAC name
  • 1-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18N2O
Molar mass218.300 g·mol−1
3D model (JSmol)
SMILES
  • CN(C)CCc(cn1C)c2c1cccc2O
InChI
  • 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 produce a head-twitch response in mice that are 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 hallucinogenic side effects they produce, which are considered undesirable. 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 BL, Toth BA, He P, Shuster L (October 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 RA, Halpern JH, Pope HG (June 2006). "Response of cluster headache to psilocybin and LSD". Neurology. 66 (12): 1920–2. doi:10.1212/01.wnl.0000219761.05466.43. PMID 16801660. S2CID 31220680.
  3. ↑ Halberstadt AL, Koedood L, Powell SB, Geyer MA (November 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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