Norpsilocin

Norpsilocin
Names
	IUPAC name 3-[2-(methylamino)ethyl]-1H-indol-4-ol
	Other names 4-Hydroxy-N-methyltryptamine; AS-63499;
Identifiers
CAS Number	28363-70-4;
3D model (JSmol)	Interactive image;
ChemSpider	27283888;
PubChem CID	14107683;
	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;
	SMILES CNCCC1=CNC2=C1C(=CC=C2)O;
Properties
Chemical formula	C11H14N2
Molar mass	174.247 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

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] Norpsiloin was found to be a full agonist of 5-HT2A 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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[pmid28929753-1] 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.

[crystallinepsilocin-2] "Two New Crystalline Forms of Norpsilocin".

[3] "Study Finds Norpsilocin is More Potent Than Psilocin at 5-HT2A".

[pmid32077284-4] 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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[2]

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Norpsilocin

See also[]

References[]