1-Methylpsilocin

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 ;
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 (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 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]

References

^ ^a ^b 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): 4555–4559. doi:10.1016/j.bmcl.2005.06.104. PMID 16061378.
^ ^a ^b Sewell RA, Halpern JH, Pope HG (June 2006). "Response of cluster headache to psilocybin and LSD". Neurology. 66 (12): 1920–1922. doi:10.1212/01.wnl.0000219761.05466.43. PMID 16801660. S2CID 31220680.
^ ^a ^b 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): 1548–1561. doi:10.1177/0269881110388326. PMC 3531560. PMID 21148021.

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[SardKumaranMorencyRoth2005-1] 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): 4555–4559. doi:10.1016/j.bmcl.2005.06.104. PMID 16061378.

[SewellHalperonPope2006-2] Sewell RA, Halpern JH, Pope HG (June 2006). "Response of cluster headache to psilocybin and LSD". Neurology. 66 (12): 1920–1922. doi:10.1212/01.wnl.0000219761.05466.43. PMID 16801660. S2CID 31220680.

[HalberstadtKoedoodPowell2011-3] 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): 1548–1561. doi:10.1177/0269881110388326. PMC 3531560. PMID 21148021.

[1]

[2]

[3]

1-Methylpsilocin

See also

References