Aeruginascin

Aeruginascin

Clinical data
ATC code	none
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Class A
Identifiers
IUPAC name [3-[2-(Trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate
CAS Number	114264-95-8 Y
PubChem CID	60208479
ChemSpider	26233970 Y
UNII	7U9WQY1P7R
CompTox Dashboard (EPA)	DTXSID60921308
Chemical and physical data
Formula	C13H20N2O4P
Molar mass	299.287 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[N+](C)(C)CCc1c[nH]c2c1c(ccc2)OP(=O)(O)[O-]
InChI InChI=1S/C13H19N2O4P/c1-15(2,3)8-7-10-9-14-11-5-4-6-12(13(10)11)19-20(16,17)18/h4-6,9,14H,7-8H2,1-3H3,(H-,16,17,18) Y Key:OIIPFLWAQQNCHA-UHFFFAOYSA-N Y
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Aeruginascin or N,N,N-trimethyl-4-phosphoryloxytryptamine is an indoleamine derivative which occurs naturally within the mushrooms Inocybe aeruginascens and Pholiotina cyanopus, and Psilocybe cubensis. Aeruginascin is the N-trimethyl analogue of psilocybin. It is closely related to the frog skin toxin bufotenidine (5-HTQ), a potent 5-HT₃ receptor agonist, but the aeruginascin metabolite 4-HO-TMT shows strong binding at the 5-HT2 receptors similar to psilocin. The first scientific literature about the pharmacological effects of aeruginascin is from a study published by Gartz in 1989. Across 23 analyzed cases of accidental hallucinogenic mushroom poisonings, people who had ingested the mushroom Inocybe aeruginascens reported only euphoric experiences. This is in contrast to the slight and in some cases extremely dysphoric experiences reported from the accidental ingestion of non aeruginascin containing mushrooms (containing solely psilocybin and psilocin).

Inocybe aeruginascens