1-Methylpsilocin

1-Methylpsilocin (developmental code names CMY, CMY-16) is a tryptamine derivative developed by Sandoz which acts as a selective agonist of the serotonin 5-HT_2C receptor (IC₅₀Tooltip half-maximal inhibitory concentration 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-HT_2C than 5-HT_2A, it does produce a head-twitch response in mice that is dependent on 5-HT_2A, so it is not entirely free of effects on 5-HT_2A in vivo. In contrast to psilocin, 1-methylpsilocin did not activate 5-HT_1A receptors in mice.^[1][2][3]

1-Methylpsilocin

Clinical data
Other names	CMY; CMY-16; 3-(2-(Dimethylamino)ethyl)-1-methyl-indol-4-ol
Identifiers
IUPAC name 1-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole
CAS Number	1465-16-3 Y
PubChem CID	44404883
ChemSpider	21686519
UNII	65MKC68UST
ChEMBL	ChEMBL197664
CompTox Dashboard (EPA)	DTXSID40658761
Chemical and physical data
Formula	C13H18N2O
Molar mass	218.300 g·mol−1
3D model (JSmol)	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 has been investigated for applications such as treatment of glaucoma, obsessive–compulsive disorder (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

• 1-Methyltryptamine
• 1-Propyl-5-MeO-AMT
• 2-Bromo-LSD
• CP-132,484
• Lespedamine (1-methoxy-DMT)
• O-4310