Aeruginascin
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| 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 |
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| Formula | C13H20N2O4P |
| Molar mass | 299.287 g·mol−1 |
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Use and effects
The first report about the possible effects of aeruginascin is from a study published by Jochen Gartz in 1989.[13] Across 23 analyzed cases of accidental hallucinogenic mushroom poisonings, people who had ingested the mushroom Inocybe aeruginascens reported only euphoric experiences.[14][15] 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).[15] However, these findings are anecdotal and preliminary.[15]
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.[16][17] Unlike psilocybin, but similarly to 4-HO-TMT, aeruginascin does not produce the head-twitch response in rodents.[18][19] It lacks affinity or activation of the mouse 5-HT2A and 5-HT1A receptors.[19]
Chemistry
Analogues
Analogues of aerguinascin include 4-HO-TMT, norbaeocystin (4-PO-T), 4-hydroxytryptamine (4-HT or 4-HO-T), baeocystin (4-PO-NMT), norpsilocin (4-HO-NMT), psilocybin (4-PO-DMT), psilocin (4-HO-DMT), and ethocybin (4-PO-DET), among others.