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| Other names | Norpsilocybin;N-Desmethylpsilocybin; 4-Phosphoryloxy-N-methyltryptamine; 4-PO-NMT; 4-Hydroxy-N-methyltryptamine 4-phosphate; PLZ-1019; PLZ1019 |
| Routes of administration | Oral |
| Drug class | Serotonin receptor agonist;Serotonin5-HT2A receptoragonist |
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| Formula | C11H15N2O4P |
| Molar mass | 270.225 g·mol−1 |
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Baeocystin, also known asnorpsilocybin or4-phosphoryloxy-N-methyltryptamine (4-PO-NMT), is azwitterionicalkaloid of thetryptamine family and ananalogue ofpsilocybin (4-PO-DMT). It is found as a minor compound in mostpsilocybin mushrooms together with psilocybin,psilocin (4-HO-DMT),norbaeocystin (4-PO-T), andaeruginascin (4-PO-TMT).[1] The compound is theN-demethylatedderivative of psilocybin and the 4-phosphorylated derivative ofnorpsilocin (4-HO-NMT).
Chemist andmycologistJochen Gartz reported in the 1990s that baeocystin is active as apsychedelic in humans.[2][3][4][5][6][7] He has stated that 4 mg produced a "threshold" or "gentlehallucinogenic experience" with "mildhallucinations for three hours" and that "10 mg of baeocystin [was] found to be about as psychoactive as a similar amount of psilocybin".[2][3][4][5][6] Gartz also personally communicated these findings toJonathan Ott, who has reproduced the claims.[5][6][7]Hamilton Morris has expressed surprise and skepticism about the reportedpsychoactivity of baeocystin however.[7]
Gartz has also claimed that mushrooms with high baeocystin content, such asPsilocybe semilanceata, are more frequently associated withdysphoric experiences.[8][9] Conversely, he has claimed that accidental ingestion ofInocybe aeruginascens, which contains high levels of bothaeruginascin (4-PO-TMT) and baeocystin, is usually associated witheuphoric experiences, in contrast to the dysphoric experiences that can occur with mushrooms containing only high levels ofpsilocybin.[8][9] However, more research is needed on the effects of baeocystin and aeruginascin in humans.[8][9]
In contrast to Gartz, mycologistPaul Stamets has reported that he tried 10 mg pure baeocystin and that it didn't produce hallucinogenic effects, but did producepupil dilation and apparentanxiolysis.[10][11][12]
Baeocystin is thought to be aprodrug ofnorpsilocin, analogously to howpsilocybin is a prodrug ofpsilocin.[13] Norpsilocin is apotent andcentrally penetrantagonist of theserotonin5-HT2A receptor and also interacts with otherserotonin receptors.[13]
Baeocystin and norpsilocin have been found to be inactive in terms ofhallucinogen-like effects in rodents in multiple studies published in the 2020s.[14][15][13] More specifically, they were unable to produce thehead-twitch response (HTR), a well-established behavioral proxy ofpsychedelic effects, and this was in contrast topsilocybin.[14][15][13] In one of the papers, the researchers concluded that "...baeocystin alone would likely not induce hallucinogenic effectsin vivo".[14] As with baeocystin and norpsilocin,norbaeocystin,aeruginascin,4-hydroxytryptamine (4-HT), and4-HO-TMT also all failed to induce the HTR in rodents.[14][15][13] However, these compounds have not necessarily been inactive in terms of behavioral effects in general.[15][13]
The reasons for the apparently non-hallucinogenic nature of norpsilocin, baeocystin, and related compounds in animals (and possibly in humans), in spite of norpsilocin and others being potent serotonin 5-HT2A receptor agonists and producing other centrally mediated behavioral effects in animals, remain unknown.[13][15] One possibility however is that these compounds may bebiased agonists of the serotonin 5-HT2A receptor and may not sufficiently activate theintracellular signaling cascades responsible for psychedelic effects.[13][15] On the other hand, a 2025animal study found that both baeocystin and norpsilocin areperipherally selective with very limited ability to cross theblood–brain barrier.[16]
Analogues of baeocystin include4-HO-NMT,norbaeocystin (4-PO-T),psilocybin (4-PO-DMT),psilocin (4-HO-DMT),ethocybin (4-PO-DET), andaeruginascin (4-PO-TMT), among others.
Baeocystin was first isolated from the mushroomPsilocybe baeocystis,[17] and later fromP. semilanceata,[18]Panaeolus renenosus,Panaeolus subbalteatus, andCopelandia chlorocystis.[19]
Baeocystin was firstsynthesized by Troxler and colleagues in 1959.[20]
Baeocystin is being evaluated by Pilz Bioscience ("pilz" beingGerman for "mushroom") under the developmental code name PLZ-1019 for the possible treatment ofpervasive developmental disorders likeautism in children.[21]
Early controlled studies of the psychoactivity of various species in the former Czechoslovakia concluded thatPsilocybe semilanceata is a more potently psychoactive species thanPsilocybe bohemica, even though both species were found to contain the same amounts of psilocybin. Thus, researchers hypothesized that the mushrooms are likely to contain additional substances that contribute to the overall psychotropic effect. This hypothesis is supported by the fact that considerable amounts of baeocystin are consistently found in samples ofPsilocybe semilanceata. I am also aware of an experiment whose results showed that 4 mg of baeocystin caused mild hallucinations for three hours, while 10 mg of baeocystin were found to be about as psychoactive as a similar amount of psilocybin.
[Translated: In earlier controlled studies on the psychoactivity of various species in the former Czechoslovakia, it was already possible to prove that, with the same psilocybin content, Psilocybe semilanceata was more potent than Psilocybe bohemica (Chapter 2.3). The hypothesis put forward that other substances in the mushrooms must also contribute to the psychotropic effect is confirmed by the regular detection of baeocystin in considerable quantities in Psilocybe semilanceata. I know of one experiment in which 4 mg of baeocystin produced a mild hallucinosis lasting three hours, and 10 mg was approximately identical to the effect of the same amount of psilocybin.]
Psilocybe semilanceata is a species that blues inconsistently. The high levels of psilocybin and baeocystin making it one of the most potent species as well as one of the most constant in amount in comparison with other species (GARTZ & MÜLLER, 1989; Semerdzieva et al., 1986). In a self experiment a small sample of baeocystin from Psilocybe semilanceata (GARTZ, 1989b) (4 mg) has caused a gentle hallucinogenic experience. [...] GARTZ J., 1989b - Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe. Journal of Basic Microbiology, 29: 347-352. [Note: There was, strangely, no actual information in the cited paper (Gartz, 1989b) about the psychoactivity of baeocystin.]
Baeocystin [...] Pharmacology: psychoptic in 10 mg oral dose; 4 mg threshold (Gartz, pers. com.); active in animals (Cerletti, Advances in Pharmacology 6B: 233, 1968)
Baeocystin [...] Activity: Psychoactive in animals. Ott 1996 cited Cerletti 1968 [Cerletti et al. 1968 evaluated 4-HO-MMT rather than Baeocystine. See comments under its entry] Dose: Psychoptic in human with a 10 mg oral dose (4 mg threshold) (Ott 1996 cited Gartz, pers. comm.) See: Ott 1996: Entry #3, page 431 [...] Ott, Jonathan (1996) Pharmacotheon. Entheogenic Drugs, their Plant Sources and History. Second Edition Densified. Natural Products Co., Kennewick, WA 639 pp. ISBN 0-9614234-8-x (Hardcover)/ 0-9614234-9-8 (paperback)
[Morris:] Do you have any thoughts about some of the remaining uncharacterized tryptamines or lesser-characterized tryptamines like baeocystin or lespedamine? [Ott:] Sorry, what was the question? [Morris:] Baeocystin? Do you have any—seems like nobody has done an authoritative bioassay of the isolated material. [Ott:] Yeah, not authoritative but it is active. Jochen Gartz bioassayed it. [Morris:] I know I saw that you wrote that but he— [Ott:] But not norbaeocystin. He just told me that probably, maybe he hasn't published it. [Morris:] It's such a bizarre—I've heard that as well but it seems so unlikely and weird. [Ott:] And also the mono—I mean I would say there's potentially six active tryptamines there. I mean, we have the 4-phosphoryloxy-DMT, 4-hydroxy-DMT, monomethyl analogues and the tryptamine analogues. They're all potentially active and could well explain the subtle differences that many people experience between different Psilocybe species.
Anecdotal and preliminary research suggests that the biological outcome experi enced by humans following ingestion of psychedelic mushrooms is not strictly a result of psilocybin or psilocin and that there are other com pounds that interact to alter the psychoactive and/or medicinal expe rience. Gartz (1989a, 1989b) evaluated data from 24 cases of accidental ingestion of Inocybe aeruginascens, a species of mushroom with high concentrations of aeruginascin and baeocystin (Gartz, 1989a, 1989b). Of particular note, Gartz (1989a, 1989b) reported that in all cases of accidental ingestion, patients only experienced euphoric responses, in contrast to frequent reports of slight, and sometimes deep, dysphoric outcomes from people who ingested mushrooms with high levels of psilocybin and psilocin without aeruginascin. The author concluded that aeruginascin can modify the pharmacological action of psilocybin. In contrast, they also reported that use of mushrooms with high levels of baeocystin, such as P. semilanceata, lead to higher rates of dysphoric experiences (Gartz, 1989a, 1989b).
Because of some similarities with edible mushrooms like Marasmius oreades (Bolt.: Fr.) Fr., I. aeruginascens has caused 20 accidental hallucinogenic poisonings in the GDR and also one case in Hungary (3, 6, 7, 8) as well as 3 further unpublished psychoses with visual hallucinations. In all of these cases only euphoric experiences were reported. This is in contrast to the often slight and in some cases deep dysphoric mood observed in people who used mushrooms with a content of psilocybin and psilocin for hallucinogenic purposes(1, 11, 13, 14, 17). It is well known that one's experience with hallucinogens depends upon a host of environmental, cultural and psychological factors (setting and set) (12) as well as the amounts and potency of the used psilocybian species. But in a similar context, accidental ingestion of these mushrooms or other hallucinogens produced in known cases psychosis with anxiety, panic and physical symptoms while a variety of perceptual disorders may also be present (4,12). It seems that the significant amounts of the indole derivative aeruginascin can modify the pharmacological action of psilocybin to give an euphoric mood during psychosis with hallucinations due to ingestion of I. aeruginascens. Additionally, baeocystin was often found in psilocybian mushrooms and pharmacological or clinical studies are lacking. But by use of mushrooms with a high content of baeocystin like R semilanceuta (2, 10, 16) a lot of dysphoric experiences were also described (1 1, 13, 14, 17). In order to establish the specific action of aeruginascin, investigations of human ingestion of aeruginascin with and without additional application of psilocybin should be done.
Although little is known about the effects of baeocystin in isolation, Jochen Gartz, a chemist and mycologist at the Institute for Biotechnology in Germany, made anecdotal references to its psychoactivity being comparable to psilocybin in his book, "Magic Mushrooms Around the World" published in the 1997. In somewhat of a contradiction, famous mycologist Paul Stamets recently reported on The Joe Rogan podcast in 2019 that a pure baeocystin experience during a high state of anxiety didn't cause psilocybin-like hallucinations, but did dilate his pupils and cause his anxiety to disappear.
I obtained some pure baeocystin from a laboratory. [...] Since there were no reports in the scientific literature [...] with a doctor friend of mine who measured my vitals [...] we did an n of 1 study. [...] I could find no one who had ever ingested this, so I decided I would ingest it. [...] So I had super high anxiety. [...] I did 10 milligrams of baeocystin. She measured my heart beat, blood pressure, all those metrics. My eyes did dilate. She said that was good, so had a drug-like effect. [...] I didn't get high. No, not at all. She goes "how do you feel?" And I said "I feel great. I have no anxiety." [...] So here we found an analogue of psilocybin that does not get you high, that's legal, that reduced anxiety.
Notably, mushroom expert Paul Stamets recently described a similar lack of psychoactive activity upon ingesting pure baeocystin. In an interview with Joe Rogan, Stamets says he took 10 mg of baeocystin but did not feel high. He said, I was ready for liftoff. I was hoping for liftoff, I know what liftoff feels like, and I didn't get it.
