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baeocystin

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baeocystin

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Baeocystin, also known as norpsilocybin or '4-phosphoryloxy-N-methyltryptamine (4-PO-NMT'), is a zwitterionic alkaloid of the tryptamine family and an analogue of psilocybin (4-PO-DMT). It is found as a minor compound in most psilocybin mushrooms together with psilocybin, psilocin (4-HO-DMT), norbaeocystin (4-PO-T), and aeruginascin (4-PO-TMT). The compound is the N-demethylated derivative of psilocybin and the 4-phosphorylated derivative of norpsilocin (4-HO-NMT).

Chemical data

Formula
C11H15N2O4P
Molecular weight
270.22 g/mol
IUPAC name
[3-[2-(methylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate
SMILES
CNCCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
InChIKey
WTPBXXCVZZZXKR-UHFFFAOYSA-N
XLogP
-2.1
Polar surface area
94.6 Ų
H-bond donors
4
H-bond acceptors
5
Formal charge
0

via PubChem

Wikidata facts

Has part
carbon
Mass
270.077
Show 4 more facts
found in taxon
Panaeolus cyanescens
chemical formula
C₁₁H₁₅N₂O₄P
canonical SMILES
CNCCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
Commons category
Baeocystin
Sources (2)

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~5 min read

Encyclopedic overview

10 sections
Contents
  • Use and effects
  • Interactions
  • Pharmacology
  • Chemistry
  • Analogues
  • Natural occurrence
  • History
  • Research
  • See also
  • References

Baeocystin, also known as norpsilocybin or '4-phosphoryloxy-N-methyltryptamine (4-PO-NMT'), is a zwitterionic alkaloid of the tryptamine family and an analogue of psilocybin (4-PO-DMT). It is found as a minor compound in most psilocybin mushrooms together with psilocybin, psilocin (4-HO-DMT), norbaeocystin (4-PO-T), and aeruginascin (4-PO-TMT). The compound is the N-demethylated derivative of psilocybin and the 4-phosphorylated derivative of norpsilocin (4-HO-NMT).

==Use and effects== Chemist and mycologist Jochen Gartz reported in the 1990s that baeocystin is active as a psychedelic in humans. He has stated that 4mg produced a "threshold" or "gentle hallucinogenic experience" with "mild hallucinations for three hours" and that "10mg of baeocystin [was] found to be about as psychoactive as a similar amount of psilocybin". Gartz also personally communicated these findings to Jonathan Ott, who has reproduced the claims. Hamilton Morris has expressed surprise and skepticism about the reported psychoactivity of baeocystin however.

Excerpted from Wikipedia’s “baeocystin” article, available under the CC BY-SA 4.0 licence.