Aeruginascin, also known as 4-phosphoryloxy-''N'',''N'',''N''-trimethyltryptamine (4-PO-TMT), is an

indoleamine Indolamines are a family of neurotransmitters that share a common molecular structure. Indolamines are a classification of monoamine neurotransmitter, along with catecholamines and ethylamine derivatives. A common example of an indolamine is the ...

derivative which occurs naturally within the mushrooms '' Inocybe aeruginascens'', ''

Pholiotina cyanopus ''Conocybula 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 ...

'', and ''

Psilocybe cubensis ''Psilocybe cubensis'', commonly known as the magic mushroom, shroom, golden halo, golden teacher, cube, or gold cap, is a species of psilocybin mushroom of moderate potency whose principal Psychoactive compound, active compounds are psilocybin ...

''. It was discovered by

Jochen Gartz Jochen Gartz (born 1 October, 1953) was a German chemist and mycologist who studied psilocybin mushrooms as well as other psychoactive plants. He was considered an expert in this field. Among other accomplishments, Gartz is known for discovering ...

Pharmacology

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 (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...

analogue of

psilocybin Psilocybin, also known as 4-phosphoryloxy-''N'',''N''-dimethyltryptamine (4-PO-DMT), is a natural product, naturally occurring tryptamine alkaloid and Investigational New Drug, investigational drug found in more than List of psilocybin mushroom ...

. It is closely related to the frog skin toxin

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

(5-HTQ), a potent

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT₃ receptor agonist, but the aeruginascin

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

4-HO-TMT (thought to be its active form) shows strong binding at the serotonin 5-HT₂ receptors similar to

psilocin Psilocin, also known as 4-hydroxy-''N'',''N''-dimethyltryptamine (4-HO-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocy ...

. Aeruginascin itself has been found to have high

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

for the serotonin 5-HT_1A, 5-HT_2A, and 5-HT_2B receptors, but does not bind to the 5-HT₃ receptor. Unlike psilocybin, but similarly to 4-HO-TMT, aeruginascin does not produce the

head-twitch response The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lys ...

in rodents. It lacks affinity or activation of the mouse 5-HT_2A and 5-HT_1A receptors. 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 Euphoria ( ) is the experience (or affect) of pleasure or excitement and intense feelings of well-being and happiness. Certain natural rewards and social activities, such as aerobic exercise, laughter, listening to or making music and danci ...

experiences. This is in contrast to the slight and in some cases extremely

dysphoric Dysphoria (; ) is a profound state of unease or dissatisfaction. It is the semantic opposite of euphoria. In a psychiatric context, dysphoria may accompany depression, anxiety, or agitation. In psychiatry Intense states of distress and uneas ...

experiences reported from the accidental ingestion of non-aeruginascin-containing mushrooms (containing solely psilocybin and psilocin). However, these findings are

anecdotal Anecdotal evidence (or anecdata) is evidence based on descriptions and reports of individual, personal experiences, or observations, collected in a non- systematic manner. The term ''anecdotal'' encompasses a variety of forms of evidence. This ...

and preliminary. :

References

{{Tryptamines Mycotoxins Non-hallucinogenic 5-HT2A receptor agonists Peripherally selective drugs 4-Phosphoryloxytryptamines Prodrugs Psychedelic tryptamines Quaternary ammonium compounds Serotonin receptor agonists N,N,N-Trialkyltryptamines

Pharmacology

See also

References