Aeruginascin

Aeruginascin, also known as 4-phosphoryloxy-N,N,N-trimethyltryptamine (4-PO-TMT), is an indoleamine derivative which occurs naturally within the mushrooms Inocybe aeruginascens,^{[1][2][3][4][5][6]} Pholiotina cyanopus,^[6] and Psilocybe cubensis.^[7] It was discovered by Jochen Gartz.^{[8][9][10][11][12]}

Aeruginascin

Clinical data
Other names	4-Phosphoryloxy-N,N,N-trimethyltryptamine; 4-PO-TMT; 4-PO-N,N,N-TMT; 4-Hydroxy-N,N,N-trimethyltryptamine 4-phosphate
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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Pharmacology

Aeruginascin is the N-trimethyl analogue of psilocybin. It is closely related to the frog skin toxin bufotenidine (5-HTQ), a potent serotonin 5-HT₃ receptor agonist, but the aeruginascin metabolite 4-HO-TMT (thought to be its active form) shows strong binding at the serotonin 5-HT₂ receptors similar to psilocin.^[13][14] Aeruginascin itself has been found to have high affinity for the serotonin 5-HT_1A, 5-HT_2A, and 5-HT_2B receptors, but does not bind to the 5-HT₃ receptor.^[15] Unlike psilocybin, but similarly to 4-HO-TMT, aeruginascin does not produce the head-twitch response in rodents.^[16][17] It lacks affinity or activation of the mouse 5-HT_2A and 5-HT_1A receptors.^[17]

The first scientific literature about the pharmacological effects of aeruginascin is from a study published by Gartz in 1989.^[18] Across 23 analyzed cases of accidental hallucinogenic mushroom poisonings, people who had ingested the mushroom Inocybe aeruginascens reported only euphoric experiences.^[19][20] 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).^[20] However, these findings are anecdotal and preliminary.^[20]

Inocybe aeruginascens

See also

• 4-Hydroxytryptamine