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baeocystin
Sign in to saveBaeocystin, 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)
via Wikidata · CC0
~5 min read
Encyclopedic overview
10 sectionsContents
- 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.