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-hallucinogenicserotonin5-HT2A receptoragonist
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
PubChemCID	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
(verify)

Norbaeocystin, also known as4-phosphoryloxytryptamine (4-PO-T), is apsilocybin mushroomalkaloid of thetryptamine family and ananalogue ofpsilocybin (4-PO-DMT). It is found as a minor compound in mostpsilocybin mushrooms, together with psilocybin,psilocin (4-HO-DMT),aeruginascin (4-PO-TMT), andbaeocystin (4-PO-NMT), from which it is aderivative.^[1][2]

Norbaeocystin (4-PO-T) is thought to be aprodrug of4-hydroxytryptamine (4-HT), analogously to howpsilocybin (4-PO-DMT) is a prodrug ofpsilocin (4-HO-DMT) andbaeocystin (4-PO-NMT) is thought to be a prodrug ofnorpsilocin (4-HO-NMT).^[3][4] 4-HT is apotent andcentrally penetrantserotonin5-HT_2A receptoragonist and also interacts with otherserotonin receptors.^[3] In spite of this however, 4-HT and norbaeocystin do not produce thehead-twitch response, a behavioral proxy ofpsychedelic effects, in animals, and hence are putatively non-hallucinogenic.^[3][4] The reasons for this are unknown, but may be due toβ-arrestin2-preferringbiased agonism of the serotonin 5-HT_2A receptor.^[3]

Norbaeocystin is anN-demethylatedderivative ofbaeocystin (itself anN-demethylated derivative ofpsilocybin), and aphosphorylated derivative of4-hydroxytryptamine (4-HT).^{[citation needed]} The latter is notable as apositional isomer ofserotonin, which is 5-hydroxytryptamine (5-HT).^{[citation needed]}

Derivatives of norbaeocystin (4-PO-T), also known assubstituted 4-phosphoryloxytryptamines, includebaeocystin (4-PO-NMT),psilocybin (4-PO-DMT),ethocybin (4-PO-DET),4-PO-DiPT,4-PO-MET, andaeruginascin (4-PO-TMT), among others.

• Substituted tryptamine

• Drugs not assigned an ATC code
• Experimental non-hallucinogens
• Non-hallucinogenic 5-HT2A receptor agonists
• 4-Phosphoryloxytryptamines
• Prodrugs
• Psychedelic tryptamines
• Tryptamine alkaloids

• Articles with short description
• Short description matches Wikidata
• Short description is different from Wikidata
• Chemical pages without DrugBank identifier
• All articles with unsourced statements
• Articles with unsourced statements from October 2025