Baeocystin

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Baeocystin
Baeocystin Formula V.1.svg
Baeocystin zwitterion 3D spacefill.png
Clinical data
Other namesNorpsilocybin; N-Desmethylpsilocybin; 4-Phosphoryloxy-N-methyltryptamine; 4-PO-NMT; 4-Hydroxy-N-methyltryptamine 4-phosphate; PLZ-1019
Routes of
administration 		Oral
ATC code
  • None
Legal status
Legal status
Identifiers
  • 3-[2-(Methylammonio)ethyl]-1H-indol-4-yl hydrogenphosphate
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H15N2O4P
Molar mass 270.225 g·mol−1
3D model (JSmol)
  • CNCCc1c[nH]c2cccc(OP(=O)(O)O)c12
  • InChI=1S/C11H15N2O4P/c1-12-6-5-8-7-13-9-3-2-4-10(11(8)9)17-18(14,15)16/h2-4,7,12-13H,5-6H2,1H3,(H2,14,15,16) Yes check.svgY
  • Key:WTPBXXCVZZZXKR-UHFFFAOYSA-N Yes check.svgY
   (verify)

Baeocystin, also known as norpsilocybin or 4-phosphoryloxy-N-methyltryptamine (4-PO-NMT), is a zwitterionic alkaloid and analogue of psilocybin. It is found as a minor compound in most psilocybin mushrooms together with psilocybin, norbaeocystin, aeruginascin, and psilocin. [1] Baeocystin is an N-demethylated derivative of psilocybin, and a phosphorylated derivative of 4-HO-NMT (4-hydroxy-N-methyltryptamine). The structures at right illustrate baeocystin in its zwitterionic form.

Contents

Baeocystin was first isolated from the mushroom Psilocybe baeocystis , [2] and later from P. semilanceata , [3] Panaeolus renenosus , Panaeolus subbalteatus , and Copelandia chlorocystis . [4] It was first synthesized by Troxler et al. in 1959. [5]

Pharmacology

Little information exists with regard to the human pharmacology of baeocystin. However, chemist and mycologist Jochen Gartz has reported that baeocystin is active as a psychedelic in humans. [6] [7] [8] [9] [10] [11] He has stated that 4 mg produced a "threshold" or "gentle hallucinogenic experience" with "mild hallucinations for three hours" and that "10 mg of baeocystin [was] found to be about as psychoactive as a similar amount of psilocybin". [6] [7] [8] [9] [10] Gartz also personally communicated these findings to Jonathan Ott, who has reproduced the claims. [9] [10] [11] Hamilton Morris has expressed surprise and skepticism about the reported psychoactivity of baeocystin however. [11]

While Gartz describes baeocystin as being active, this could not be replicated in a mouse model in a 2019 study which found no evidence that baeocystin produces any hallucinogen-like effects. [12] Researchers compared psilocybin which is a known hallucinogen to baeocystin by using the mouse head-twitch response. [12] Upon comparison, baeocystin was indistinguishable from saline solution, indicating "...baeocystin alone would likely not induce hallucinogenic effects in vivo". [12] This does contrast however with the human experiences mentioned above, although high quality data is scarce. [12]

Baeocystin is thought to be a prodrug of norpsilocin, analogously to how psilocybin is a prodrug of psilocin. [13] Norpsilocin is a potent and centrally penetrant agonist of the serotonin 5-HT2A receptor and also interacts with other serotonin receptors. [13] The reasons for the apparently non-hallucinogenic nature of norpsilocin and baeocystin remain unknown. [13]

Development

The compound is being evaluated under the developmental code name PLZ-1019 for the possible treatment of pervasive developmental disorders in children. [14]

See also

Related Research Articles

<span class="mw-page-title-main">Psilocybin</span> Chemical compound found in some species of mushrooms

Psilocybin, also known as 4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT), and formerly sold under the brand name Indocybin, is a naturally occurring psychedelic prodrug compound produced by more than 200 species of fungi. Psilocybin is itself biologically inactive but is quickly converted by the body to psilocin, which has mind-altering effects similar, in some aspects, to those of other classical psychedelics. Effects include euphoria, hallucinations, changes in perception, a distorted sense of time, and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.

<i>Psilocybe cubensis</i> Species of fungus

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 active compounds are psilocybin and psilocin. It belongs to the fungus family Hymenogastraceae and was previously known as Stropharia cubensis. It is the best-known psilocybin mushroom due to its wide distribution and ease of cultivation.

<span class="mw-page-title-main">Psilocybin mushroom</span> Mushrooms containing psychoactive indole alkaloids

Psilocybin mushrooms, commonly known as magic mushrooms,shrooms, or broadly as hallucinogenic mushrooms, are a polyphyletic informal group of fungi that contain psilocybin, which turns into psilocin upon ingestion. The most potent species are members of genus Psilocybe, such as P. azurescens, P. semilanceata, and P. cyanescens, but psilocybin has also been isolated from approximately a dozen other genera, including Panaeolus, Inocybe, Pluteus, Gymnopilus, and Pholiotina.

<i>Psilocybe</i> Genus of fungi

Psilocybe is a genus of gilled mushrooms, growing worldwide, in the family Hymenogastraceae. Many species contain the psychedelic compounds psilocybin and psilocin.

<i>Psilocybe semilanceata</i> Species of fungus in the family Hymenogastraceae, native to Europe

Psilocybe semilanceata, commonly known as the liberty cap, is a species of fungus which produces the psychoactive compounds psilocybin, psilocin and baeocystin. It is both one of the most widely distributed psilocybin mushrooms in nature, and one of the most potent. The mushrooms have a distinctive conical to bell-shaped cap, up to 2.5 cm (1 in) in diameter, with a small nipple-like protrusion on the top. They are yellow to brown, covered with radial grooves when moist, and fade to a lighter color as they mature. Their stipes tend to be slender and long, and the same color or slightly lighter than the cap. The gill attachment to the stipe is adnexed, and they are initially cream-colored before tinting purple to black as the spores mature. The spores are dark purplish-brown en masse, ellipsoid in shape, and measure 10.5–15 by 6.5–8.5 micrometres.

<i>Psilocybe cyanescens</i> Species of fungus

Psilocybe cyanescens, commonly known as the wavy cap or potent psilocybe, is a species of potent psychedelic mushroom. The main compounds responsible for its psychedelic effects are psilocybin and psilocin. It belongs to the family Hymenogastraceae. A formal description of the species was published by Elsie Wakefield in 1946 in the Transactions of the British Mycological Society, based on a specimen she had recently collected at Kew Gardens. She had begun collecting the species as early as 1910. The mushroom is not generally regarded as being physically dangerous to adults. Since all the psychoactive compounds in P. cyanescens are water-soluble, the fruiting bodies can be rendered non-psychoactive through parboiling, allowing their culinary use. However, since most people find them overly bitter and they are too small to have great nutritive value, this is not frequently done.

<span class="mw-page-title-main">Norbaeocystin</span> Chemical compound

Norbaeocystin, also known as 4-phosphoryloxytryptamine (4-PO-T), is a psilocybin mushroom alkaloid and analog of psilocybin. It is found as a minor compound in most psilocybin mushrooms together with psilocin, psilocybin, aeruginascin, and baeocystin, from which it is a derivative.

<i>Psilocybe tampanensis</i> Psychedelic mushroom in the family Hymenogastraceae

Psilocybe tampanensis is a very rare psychedelic mushroom in the family Hymenogastraceae. Originally collected in the wild in a sandy meadow near Tampa, Florida, in 1977, the fungus would not be found in Florida again until 44 years later. The original Florida specimen was cloned, and descendants remain in wide circulation. The fruit bodies (mushrooms) produced by the fungus are yellowish-brown in color with convex to conic caps up to 2.4 cm (0.9 in) in diameter atop a thin stem up to 6 cm (2.4 in) long. Psilocybe tampanensis forms psychoactive truffle-like sclerotia that are known and sold under the nickname "philosopher's stones". The fruit bodies and sclerotia are consumed by some for recreational or entheogenic purposes. In nature, sclerotia are produced by the fungus as a rare form of protection from wildfires and other natural disasters.

<i>Psilocybe azurescens</i> Species of fungus

Psilocybe azurescens is a species of psychedelic mushroom whose main active compounds are psilocybin and psilocin. It is among the most potent of the tryptamine-bearing mushrooms, containing up to 1.8% psilocybin, 0.5% psilocin, and 0.4% baeocystin by dry weight, averaging to about 1.1% psilocybin and 0.15% psilocin. It belongs to the family Hymenogastraceae in the order Agaricales.

<i>Psilocybe baeocystis</i> Species of fungus

Psilocybe baeocystis is a psilocybin mushroom of the family Hymenogastraceae. It contains the hallucinogenic compounds psilocybin, psilocin and baeocystin. The species is commonly known by various names such as bottle caps, knobby tops, blue bells, olive caps.

<i>Conocybula cyanopus</i> Species of fungus

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 transferred to Conocybe by Robert Kühner in 1935 before being transferred to Pholiotina by Rolf Singer in 1950 and finally to Conocybula by T. Bau & H. B. Song in 2024. Conocybula cyanopus is recognized as the type species of Conocybula sect. Cyanopodae.

<i>Panaeolus cyanescens</i> Species of fungus

Panaeolus cyanescens is a mushroom in the Bolbitiaceae family. Panaeolus cyanescens is a common psychoactive mushroom and is similar to Panaeolus tropicalis. It is also known under the common names of Blauender Düngerling, blue meanies, faleaitu (Samoan), falter-düngerling, Hawaiian copelandia, jambur, jamur, pulouaitu (Samoan), taepovi (Samoan), tenkech (Chol).

<span class="mw-page-title-main">Aeruginascin</span> Chemical compound

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, Pholiotina cyanopus, and Psilocybe cubensis.

<i>Psilocybe fimetaria</i> Species of fungus

Psilocybe fimetaria is a dung-loving mushroom in the genus Psilocybe. Along with Psilocybe fuscofulva, it is one of two Psilocybe mushroom species that has been found to contain no detectable levels of the psychoactive tryptamines psilocin, psilocybin, or others. In the case of Psilocybe fimetaria, this may be due to some individual specimens having a very low concentration, or the species actually being a pair of morphologically similar species.

Panaeolus microsporus is a species of mushroom in the Bolbitiaceae family. It is a psychoactive species of the Panaeolus genus, containing alkaloids like psilocybin and psilosin. All Panaeolus species produce serotonin and serotonin derivatives.

<i>Psilocybe serbica</i> Species of fungus

Psilocybe serbica is a species of mushroom in the family Hymenogastraceae. The mushroom contains the psychotropic compounds psilocybin and psilocin, and also related tryptamine alkaloids baeocystin, norbaeocystin, and aeruginascin. It is closely related to Psilocybe aztecorum. It was reported as new to science by Meinhard Moser and Egon Horak in 1969. Molecular analysis published in 2010 has shown that P. serbica is the same species as Psilocybe bohemica described by Šebek in 1983, Psilocybe arcana described by Borovička and Hlaváček in 2001, and Psilocybe moravica by Borovička in 2003. Psilocybe serbica is common in Central Europe.

<i>Psilocybe pelliculosa</i> Species of fungus

Psilocybe pelliculosa is a species of fungus in the family Hymenogastraceae. The fruit bodies, or mushrooms, have a conical brownish cap up to 2 cm in diameter atop a slender stem up to 8 cm long. It has a white partial veil that does not leave a ring on the stem. American mycologist Alexander H. Smith first described the species in 1937 as a member of the genus known today as Psathyrella; it was transferred to Psilocybe by Rolf Singer in 1958.

<span class="mw-page-title-main">Norpsilocin</span> Chemical compound

Norpsilocin, also known as 4-hydroxy-N-methyltryptamine (4-HO-NMT), is a tryptamine alkaloid recently discovered in 2017 in the psychedelic mushroom Psilocybe cubensis. It is hypothesized to be a dephosphorylated metabolite of baeocystin.

<span class="mw-page-title-main">4-Hydroxytryptamine</span> Serotonin receptor agonist

4-Hydroxytryptamine, also known as N,N-didesmethylpsilocin, is a naturally occurring tryptamine alkaloid. It is closely related chemically to the neurotransmitter serotonin, the psychedelic psilocin, and is the active form of the tryptamine alkaloid norbaeocystin.

References

  1. ↑ Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M (November 2022). "Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids". International Journal of Molecular Sciences. 23 (22): 14068. doi: 10.3390/ijms232214068 . PMC   9693126 . PMID   36430546.
  2. ↑ Leung AY, Paul AG (October 1968). "Baeocystin and norbaeocystin: new analogs of psilocybin from Psilocybe baeocystis". Journal of Pharmaceutical Sciences. 57 (10): 1667–1671. doi:10.1002/jps.2600571007. PMID   5684732.
  3. ↑ Repke DB, Leslie DT, Guzmán G (1977). "Baeocystin in psilocybe, conocybe and panaeolus". Lloydia. 40 (6): 566–578. PMID   600026.
  4. ↑ Brossi A (1988). The Alkaloids: Chemistry and Pharmacology V32: Chemistry and Pharmacology. Academic Press. p. 46. ISBN   978-0-08-086556-0.
  5. ↑ Troxler F, Seeman F, Hofmann A (1959). "Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen". Helvetica Chimica Acta (in German). 42 (6): 2073–2103. doi:10.1002/hlca.19590420638.
  6. 1 2 Gartz J, Appelius C, Taake C, Falk B (1996). "The Current State of Knowledge About European Species: Psilocybe Semilanceata: The Classic Species Among European Psychotropic Mushrooms" (PDF). Magic Mushrooms Around the World: A Scientific Journey Across Cultures and Time : the Case for Challenging Research and Value Systems. Los Angeles, California: LIS Publications. pp. 16–28 (27). ISBN   978-0-9653399-0-2 . Retrieved 25 January 2025. Early controlled studies of the psychoactivity of various species in the former Czechoslovakia concluded that Psilocybe semilanceata is a more potently psychoactive species than Psilocybe 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 of Psilocybe 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.
  7. 1 2 Gartz J (1999). Narrenschwämme: Psychoaktive Pilze rund um die Welt [Magic Mushrooms: Psychoactive Mushrooms Around the World] (in German). Nachtschatten Verlag. p. 55. ISBN   978-3-03788-494-2 . Retrieved 25 January 2025. [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.]
  8. 1 2 Gartz J (1992). "Further Investigations on Psychoactive Mushrooms of the Genera Psylocibe, Gymnopilus and Conocybe" (PDF). Annali del Museo Civico di Rovereto. 7: 265–274. 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.]
  9. 1 2 3 Ott J (1996). Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History. Natural Products Company. p. 431. ISBN   978-0-9614234-9-0 . Retrieved 25 January 2025. Baeocystin [...] Pharmacology: psychoptic in 10 mg oral dose; 4 mg threshold (Gartz, pers. com.); active in animals (Cerletti, Advances in Pharmacology 6B: 233, 1968)
  10. 1 2 3 Keeper of the Trout and Friends (2007). "Baeocystin". Some Simple Tryptamines (2 ed.). Austin, Texas: Mydriatric Productions. p. 59. ASIN   B0041OLXM0. ISBN   978-0977087655. OCLC   948674100. 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)
  11. 1 2 3 Hamilton Morris (1 September 2021). "PODCAST 28: A talk with Jonathan Ott". The Hamilton Morris Podcast (Podcast). Patreon. Event occurs at 1:06:15–1:07:21. Retrieved 20 January 2025. [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.
  12. 1 2 3 4 Sherwood AM, Halberstadt AL, Klein AK, McCorvy JD, Kaylo KW, Kargbo RB, et al. (February 2020). "Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin". Journal of Natural Products. 83 (2): 461–467. doi:10.1021/acs.jnatprod.9b01061. PMID   32077284.
  13. 1 2 3 Rakoczy RJ, Runge GN, Sen AK, Sandoval O, Wells HG, Nguyen Q, et al. (October 2024). "Pharmacological and behavioural effects of tryptamines present in psilocybin-containing mushrooms". Br J Pharmacol. 181 (19): 3627–3641. doi: 10.1111/bph.16466 . PMID   38825326.
  14. ↑ "Baeocystin - Pilz Bioscience". AdisInsight. 19 January 2021. Retrieved 27 October 2024.
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