1-Methylpsilocin

1-Methylpsilocin

Identifiers
IUPAC name 1-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole
CAS Number	1465-16-3 N
PubChem CID	44404883
ChemSpider	21686519
Chemical and physical data
Formula	C13H18N2O
Molar mass	218.294 g/mol
3D model (Jmol)	Interactive image
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-HT_2C receptor (IC₅₀ of 12 nM, vs 633 nM at 5-HT_2A), and an inverse agonist at 5-HT_2B (K_i 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.