Aeruginascin or ''N,N,N''-trimethyl-4-phosphoryloxytryptamine is an

indoleamine Indolamines are a family of neurotransmitters that share a common molecular structure (namely, indolamine). Indolamines are a classification of monoamine neurotransmitter, along with catecholamines and ethylamine derivatives. A common example o ...

derivative which occurs naturally within the mushroom ''

Inocybe aeruginascens ''Inocybe aeruginascens'' is a member of the genus ''Inocybe'' which is widely distributed in Europe. The species was first documented by I. Ferencz in Ócsa, Hungary on June 15, 1965. Description ''Inocybe aeruginascens'' is a small mycorrhiz ...

'' and ''

Pholiotina cyanopus ''Pholiotina cyanopus'' is a species of fungus that contains psychoactive compounds including psilocybin and the uncommon aeruginascin. Originally described as ''Galerula cyanopus'' by American mycologist George Francis Atkinson in 1918. It was ...

''. Aeruginascin is the ''N''-tri

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...

analogue of

psilocybin Psilocybin ( , ) is a naturally occurring psychedelic prodrug compound produced by more than 200 species of fungi. The most potent are members of the genus ''Psilocybe'', such as '' P. azurescens'', '' P. semilanceata'', and '' P.&nbs ...

. It is closely related to the frog skin toxin

bufotenidine Bufotenidine, also known as 5-hydroxy-''N'',''N'',''N''-trimethyltryptammonium (5-HTQ), is a toxin related to bufotenin, serotonin, and other tryptamines which is found in the venom of a variety of toads. It acts as a selective 5-HT3 recepto ...

(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 Psilocin (also known as 4-HO-DMT, 4-hydroxy DMT, psilocine, psilocyn, or psilotsin) is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counte ...

. 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).

References

Tryptamine alkaloids Psychedelic tryptamines Mycotoxins Organophosphates {{amine-stub