Norpsilocin

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-HT2A receptor. It is also more potent than psilocin.[3][4]

Norpsilocin
Names
IUPAC name
3-[2-(methylamino)ethyl]-1H-indol-4-ol
Other names
  • 4-Hydroxy-N-methyltryptamine
  • AS-63499
Identifiers
3D model (JSmol)
ChemSpider
  • 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
  • CNCCC1=CNC2=C1C(=CC=C2)O
Properties
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

See also

References
  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.
  2. "Two New Crystalline Forms of Norpsilocin".
  3. "Study Finds Norpsilocin is More Potent Than Psilocin at 5-HT2A".
  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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