Jump to content

Baeocystin

From Wikipedia, the free encyclopedia

Baeocystin
Skeletal formula of baeocystin as a zwitterion
Space-filling model of the baeocystin molecule as a zwitterion
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
FormulaC11H15N2O4P
Molar mass270.225 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) checkY
  • Key:WTPBXXCVZZZXKR-UHFFFAOYSA-N checkY
  (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.

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

[edit]

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

[edit]

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

[edit]

References

[edit]
  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. ^ a b 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. ^ a b 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. ^ a b 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. ^ a b c 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. ^ a b c 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. ^ a b c 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. ^ a b c d 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. ^ a b c 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.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Baeocystin&oldid=1271939923"