Norbaeocystin

Norbaeocystin, also known as 4-phosphoryloxytryptamine (4-PO-T), is a psilocybin mushroom 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), aeruginascin (4-PO-TMT), and baeocystin (4-PO-NMT), from which it is a derivative.^[1][2]

Norbaeocystin

Clinical data
Other names	4-Phosphoryloxytryptamine; 4-PO-T; 4-Hydroxytryptamine 4-phosphate; 4-Hydroxytryptamine phosphate
Routes of administration	Oral
Drug class	Serotonin receptor agonist; Non-hallucinogenic serotonin 5-HT2A receptor agonist
ATC code	None
Legal status
Legal status	US: Schedule I by analogue
Identifiers
IUPAC name 3-(2-ammonioethyl)-1H-indol-4-yl hydrogen phosphate
CAS Number	21420-59-7
PubChem CID	9795063
ChemSpider	7970830
UNII	C8CA0W9FJ9
KEGG	C21778
ChEBI	CHEBI:139479 Y
CompTox Dashboard (EPA)	DTXSID601193769
Chemical and physical data
Formula	C10H13N2O4P
Molar mass	256.198 g·mol−1
3D model (JSmol)	Interactive image
SMILES NCCc1c[nH]c2cccc(OP(=O)(O)O)c12
InChI InChI=1S/C10H13N2O4P/c11-5-4-7-6-12-8-2-1-3-9(10(7)8)16-17(13,14)15/h1-3,6,12H,4-5,11H2,(H2,13,14,15) Key:IKQGYCWFBVEAKF-UHFFFAOYSA-N
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Pharmacology

Norbaeocystin (4-PO-T) is thought to be a prodrug of 4-hydroxytryptamine (4-HT), analogously to how psilocybin (4-PO-DMT) is a prodrug of psilocin (4-HO-DMT) and baeocystin (4-PO-NMT) is thought to be a prodrug of norpsilocin (4-HO-NMT).^[3][4] 4-HT is a potent and centrally penetrant serotonin 5-HT_2A receptor agonist and also interacts with other serotonin receptors.^[3] In spite of this however, 4-HT and norbaeocystin do not produce the head-twitch response, a behavioral proxy of psychedelic effects, in animals, and hence are putatively non-hallucinogenic.^[3][4] The reasons for this are unknown, but may be due to β-arrestin2-preferring biased agonism of the serotonin 5-HT_2A receptor.^[3]

Chemistry

Norbaeocystin is an N-demethylated derivative of baeocystin (itself an N-demethylated derivative of psilocybin), and a phosphorylated derivative of 4-hydroxytryptamine (4-HT).^{[citation needed]} The latter is notable as a positional isomer of serotonin, which is 5-hydroxytryptamine (5-HT).^{[citation needed]}

Derivatives

Derivatives of norbaeocystin (4-PO-T), also known as substituted 4-phosphoryloxytryptamines, include baeocystin (4-PO-NMT), psilocybin (4-PO-DMT), ethocybin (4-PO-DET), 4-PO-DiPT, 4-PO-MET, and aeruginascin (4-PO-TMT), among others.

See also

• Substituted tryptamine