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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
CompTox Dashboard (EPA)	DTXSID601193769
Chemical and physical data
Formula	C10H13N2O4P
Molar mass	256.198 g·mol
3D model (JSmol)	Interactive image
SMILES NCCc1cc2cccc(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 as 4-phosphoryloxytryptamine (4-PO-T), is a psilocybin mushroom alkaloid and analog of psilocybin. It is found as a minor compound in most psilocybin mushrooms together with psilocin, psilocybin, aeruginascin, and baeocystin, from which it is a derivative.

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

Norbaeocystin is thought to be a prodrug of 4-HT, analogously to how psilocybin is a prodrug of psilocin and baeocystin is thought to be a prodrug of norpsilocin. 4-HT is a potent and centrally penetrant serotonin 5-HT_2A receptor agonist and also interacts with other serotonin receptors. 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. The reasons for this are unknown, but may be due to β-arrestin2-preferring biased agonism of the serotonin 5-HT_2A receptor.

See also

• Aeruginascin
• Baeocystin
• Norpsilocin
• Psilocybin

References

1. Leung AY, Paul AG (October 1968). "Baeocystin and norbaeocystin: new analogs of psilocybin from Psilocybe baeocystis". Journal of Pharmaceutical Sciences. 57 (10): 1667–1671. doi:10.1002/jps.2600571007. PMID 5684732.
2. Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M (November 2022). "Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids". International Journal of Molecular Sciences. 23 (22): 14068. doi:10.3390/ijms232214068. PMC 9693126. PMID 36430546.
3. ^ Rakoczy RJ, Runge GN, Sen AK, Sandoval O, Wells HG, Nguyen Q, Roberts BR, Sciortino JH, Gibbons WJ, Friedberg LM, Jones JA, McMurray MS (October 2024). "Pharmacological and behavioural effects of tryptamines present in psilocybin-containing mushrooms". Br J Pharmacol. 181 (19): 3627–3641. doi:10.1111/bph.16466. PMID 38825326.
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". J Nat Prod. 83 (2): 461–467. doi:10.1021/acs.jnatprod.9b01061. PMID 32077284.

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