5-Methoxypsilocybin

Pharmaceutical compound From Wikipedia, the free encyclopedia

5-Methoxypsilocybin, also known as 5-MeO-psilocybin or as 5-methoxy-4-phosphoryloxy-N,N-dimethyltryptamine (5-MeO-4-PO-DMT), is a compound of the tryptamine family which has been speculated may have psychedelic effects.^[1]^[2]^[3] It is related to psilocybin (4-PO-DMT) and 5-MeO-DMT and in terms of chemical structure and can be thought of as a combination of the structural features of the two compounds.^[1] 5-Methoxypsilocybin would be anticipated to possibly act as a prodrug of psilomethoxin (5-methoxypsilocin) similarly to how psilocybin acts as a prodrug of psilocin.^[1]

Other names5-MeO-psilocybin; 5-Methoxy-4-phosphoryloxy-N,N-dimethyltryptamine; 5-MeO-4-PO-DMT; Psilomethoxybin

FormulaC₁₃H₁₉N₂O₅P

Molar mass314.278 g·mol⁻¹

3D model (JSmol)

Interactive image

Quick facts Clinical data, Other names ...

5-Methoxypsilocybin
Clinical data

Other names	5-MeO-psilocybin; 5-Methoxy-4-phosphoryloxy-N,N-dimethyltryptamine; 5-MeO-4-PO-DMT; Psilomethoxybin
Identifiers
IUPAC name 3-[2-(dimethylamino)ethyl]-5-methoxy-1H-indol-4-yl dihydrogen phosphate
Chemical and physical data
Formula	C₁₃H₁₉N₂O₅P
Molar mass	314.278 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COc1ccc2c(c1OP(=O)(O)O)c(CCN(C)C)c[nH]2
InChI InChI=1S/C13H19N2O5P/c1-15(2)7-6-9-8-14-10-4-5-11(19-3)13(12(9)10)20-21(16,17)18/h4-5,8,14H,6-7H2,1-3H3,(H2,16,17,18) Key:SLAJUARCDKZWMH-UHFFFAOYSA-N

The Church of Sacred Synthesis (formerly the Church of Psilomethoxin) claims that psilomethoxin is present in the 5-MeO-DMT-fed psilocybin mushrooms that they refer to as their sacrament and sell online.^[4]^[5]^[2]^[3] Along with psilomethoxin, 5-methoxypsilocybin may also be expected to be present in the mushrooms if their claims are true.^[1]^[2]^[3] However, a 2023 independent chemical analysis detected neither psilomethoxin nor 5-methoxypsilocybin in the church's mushrooms, but instead found the usual components of psilocybin mushrooms such as psilocybin, baeocystin, and psilocin.^[1]^[2]^[3]^[5]^[6]

References

[1]
Williamson S, Sherwood A (2 June 2023), Fungi Fiction: Analytical Investigation into the Church Of Psilomethoxin's Alleged Novel Compound Using UPLC-HRMS (PDF), ChemRxiv, doi:10.26434/chemrxiv-2023-bxxtl-v2, retrieved 11 February 2025, 5-MeO-psilocybin is a hypothetical compound that combines the structural features of both psilocybin and 5-MeO-DMT. It is characterized by a 4-phosphorylated indole ring. Presumably, if psilomethoxin is biosynthesized from 5-MeO-DMT through the same pathway that hydroxylates psilocin, then the subsequent step that phosphorylates psilocin to psilocybin via PsiK may also take place to produce 5-MeO-psilocybin. By also examining the potential presence of 5-MeO-psilocybin in the sample, our objective was to thoroughly assess the plausibility of the proposed metabolic pathway. [...] These results strongly indicate that the material distributed by the Church of Psilomethoxin does not contain the novel compound psilomethoxin (or 5-MeO-psilocybin) as claimed. Instead, the sample mainly consists of known tryptamines and other natural products expected to be present in dried Psilocybe mushrooms, specifically psilocybin and psilocin, with a trace amount of baeocystin. [...] The absence of any detectible psilomethoxin or the hypothetical compound 5-MeO-psilocybin in the analyzed sample demonstrates that the Church's assertions are not yet supported by scientific evidence.
[2]
Busby M (4 October 2023). "This Veteran-Founded Church Wants to Sell Psychedelics At Your Local Drug Store". DoubleBlind Mag. Retrieved 11 February 2025.
[3]
Nickles D (28 April 2023). "Church of Psilomethoxin, Part 1: Sacramental Skepticism. Is the Church in Denial?". Psymposia. Retrieved 11 February 2025.
[4]
Busby M (8 June 2023). "This New Church Wants to Get You High on Synthetic Toad Venom". VICE. Retrieved 8 February 2025.
[5]
Stoddard B (31 July 2024). The Production of Entheogenic Communities in the United States. Cambridge University Press. pp. 36–37. doi:10.1017/9781009429412. ISBN 978-1-009-42941-2. [Greg Lake] and [Ian Benouis] also started their own entheogenic church, the Church of Psilomethoxin, later renamed the Church of the Sacred Synthesis, a community that consumes psychoactive mushrooms.27 [...] Lake and Benouis formed this church in 2022 and it was quickly embroiled in controversy. They claimed that the church's sacrament was a novel tryptamine, or a new psychedelic. As scholars Samuel Williamson and Alexander Sherwood described the church, "The Church of Psilomethoxin claims to produce a novel tryptamine by adding 5-MeO-DMT to the substrate of cultivated Psilocybe mushrooms, which is then biosynthesized into psilomethoxin, the church's sacrament" (Williamson & Sherwood 2003, unnumbered page). People across the country joined the church by submitting an online application and were granted access to the church's sacrament, which they received via mail. The so-called "mail-order mushroom church" attracted a lot of attention; but the church received even more scrutiny and condemnation after Williamson and Sherwood conducted tests on the church's sacrament and were not able to find evidence of psilomethoxin. They did, however, find psilocybin, baeocystin, and psilocin, suggesting the church was distributing and consuming "normal" psychedelic mushrooms. They published their results in April 2023 and subsequently amended their findings in June 2023. The findings were quite damning, putting Lake and Benouis on the defensive and ultimately prompting them to change the church's name to Church of the Sacred Synthesis. Lake himself responded publicly to the controversy on the Plus Three podcast in May 2023 (Lake 2023).
[6]
Hu JC (12 April 2024). "DEA announces hearing on obscure hallucinogenic compounds; Petitioning the FDA for a public meeting on Lykos and MDMA; Psychedelic church sues for defamation". The Microdose. Substack. Retrieved 9 February 2025. 'Psychedelic' Church sues detractors for defamation: The Church of Sacred Synthesis, formerly known as the Church of Psilomethoxin, is suing its critics for defamation, libel and slander in a Texas district court, according to a new piece published in DoubleBlind. The church formerly claimed that its "sacrament", a supposedly novel psychedelic drug called psilomethoxin, was created by feeding 5-MeO-DMT to psilocybin-producing fungi. In April 2023, two chemists working at the non-profit medical research organization Usona Institute, tested a sample they claim came from an anonymous member of the church and concluded that there was no evidence it was psilomethoxin. Shortly after, the psychedelics publication Psymposia published a four-part series investigating the church and its claims. Journalist Mattha Busby reports in DoubleBlind that the civil suit names Usona, the Promega Corporation, whose founder Bill Linton also co-founded Usona, Psymposia, and a user on the social media site X.

5-Methoxypsilocybin

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