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''
and ''
Pholiotina cyanopus''.
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 ...
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 (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 cou ...
. 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
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