Norpsilocin

Norpsilocin
Clinical data
Other names	4-HO-NMT; 4-Hydroxy-N-methyltryptamine; AS-63499;
Identifiers
	IUPAC name 3-[2-(methylamino)ethyl]-1H-indol-4-ol;
CAS Number	28363-70-4;
PubChem CID	14107683;
ChemSpider	27283888;
ChEMBL	ChEMBL4648350;
CompTox Dashboard (EPA)	DTXSID901336988 ;
Chemical and physical data
Formula	C11H14N2O
Molar mass	190.246 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CNCCC1=CNC2=C1C(=CC=C2)O;
	InChI InChI=1S/C11H14N2O/c1-12-6-5-8-7-13-9-3-2-4-10(14)11(8)9/h2-4,7,12-14H,5-6H2,1H3; Key:MTJOWJUQGYWRHT-UHFFFAOYSA-N;

Norpsilocin or 4-HO-NMT is naturally occurring tryptamine alkaloid recently discovered in 2017 in one species called Psilocybe cubensis.^[1]^[2] It is said to be dephosphorylated metabolite of baeocystin however this hypothesis haven't been formally proven.^[2] Norpsilocin was found to be a full agonist of 5-HT_2A receptor. It is also more potent than psilocin.^[3]^[4]

References

^ Lenz C, Wick J, Hoffmeister D (October 2017). "Identification of ω-N-Methyl-4-hydroxytryptamine (Norpsilocin) as a Psilocybe Natural Product". Journal of Natural Products. 80 (10): 2835–2838. doi:10.1021/acs.jnatprod.7b00407. PMID 28929753.
^ ^a ^b "Two New Crystalline Forms of Norpsilocin".
^ "Study Finds Norpsilocin is More Potent Than Psilocin at 5-HT2A".
^ Sherwood AM, Halberstadt AL, Klein AK, McCorvy JD, Kaylo KW, Kargbo RB, Meisenheimer P (February 2020). "Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin". Journal of Natural Products. 83 (2): 461–467. doi:10.1021/acs.jnatprod.9b01061. PMID 32077284.

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