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  • 3-[2-(Dimethylamino)ethyl]-5-methoxy-1H-indol-4-ol
CAS Number
Chemical and physical data
Formula C13H18N2O2
Molar mass 234.299 g·mol−1
3D model (JSmol)
Melting point 146 to 147 °C (295 to 297 °F)
  • CN(C)CCc2c[nH]c1ccc(OC)c(O)c12
  • InChI=1S/C13H18N2O2/c1-15(2)7-6-9-8-14-10-4-5-11(17-3)13(16)12(9)10/h4-5,8,14,16H,6-7H2,1-3H3 Yes check.svgY
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4-Hydroxy-5-methoxydimethyltryptamine, also known as 4-HO-5-MeO-DMT or psilomethoxin, is a novel psychedelic drug. It is the 4-hydroxy counterpart of 5-MeO-DMT, or the 5-methoxy counterpart of psilocin.


Psilomethoxin, the name for the compound used by the church asserting it as their sacrament, is a tryptamine derivative considered psychedelic and currently being studied. The only report of it in the chemical literature was a paper published by Marc Julia's group at the Pasteur Institute in 1965. [1] This paper reports a 10 step synthesis of 4-HO-5-MeO-DMT from ortho-vanillin, characterizing many previously yet synthesized compounds at the time. Alexander Shulgin hypothesized that 4-OH-5-MeO-DMT can be biosynthesized from Psilocybe by feeding cell cultures 5-Meo-DMT, referencing a 1988 study by Jochen Gartz where he reportedly converted DET into 4-HO-DET and 4-PO-DET with the fungus, neither of which had ever been found in nature. [2] [3]


In the United States, 4-HO-5-MeO-DMT may be considered illegal under the Federal Analogue Act if sold or used for consumption due to structural relation to psilocin and 5-MeO-DMT, which are both listed as Schedule I controlled substances under the Controlled Substances Act of 1970.

The word "PSILOMETHOXIN" has been trademarked in the United States under code 045. [4]

Religious use

Psilomethoxin is considered a religious sacrament by the Church of Psilomethoxin, created by the non-profit corporation Church of the Sacred Synthesis based in Texas. [5] [6] which has also trademarked the word "PSILOMETHOXIN" for "Religious and spiritual services, namely, providing gatherings and retreats to develop and enhance the spiritual lives of individuals" filed under "045 - Legal services; security services for the protection of property and individuals; personal and social services rendered by others to meet the needs of individuals." [7]

Despite this, on April 12th, 2023 a study was published that analyzed a purportedly "anonymous sample" of the claimed sacred sacrament mushroom material that is sold by the church. According to study, the sample did not appear to contain any Psilomethoxin or any 5-Meo-DMT and appeared to have been typical Psilocybin mushroom material containing psilocybin and psilocin, with a trace amount of baeocystin. [8]

The church acknowledged that obtaining a reference standard for Psilomethoxin is paramount for the ability to verify or refute such claims once and for all in a response stating "Our claims to the existence of Psilomethoxin, at this time, are solely based on faith". In public interviews following their psychedelic capitalism titled response, concern is repeatedly raised regarding the study over the similarities between the church's work and a portion of the operations by the for-profit corporation ProMega Corp [9] , whose CEO is also the president of the nonprofit Usona Institute [10] that published the claims in their study. The church has advertised the addition of a scientist- telling reporters the expected completion time of a reference standard available for independent confirmation and validated sacrament testing protocols is before fall 2023 while referencing their response again "The individuals attacking and attempting to discredit our Church, seemingly operate off the erroneous assumption that the Church has made the claim that Psilomethoxin has been positively identified in its Sacrament". [11]

Related Research Articles

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

Psilocybin is a naturally occurring psychedelic prodrug compound produced by more than 200 species of fungi. The most potent are members of genus Psilocybe, such as P. azurescens, P. semilanceata, and P. cyanescens, but psilocybin has also been isolated from about a dozen other genera. 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 lysergic acid diethylamide (LSD), mescaline, and dimethyltryptamine (DMT). In general, the effects include euphoria, visual and mental hallucinations, changes in perception, 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 is a species of psilocybin mushroom of moderate potency whose principal active compounds are psilocybin and psilocin. Commonly called shrooms, magic mushrooms, golden halos, cubes, or gold caps, 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. This mushroom being optimal for home cultivation specifically, as was suggested in the 1970s, is primarily what led to cubensis being the psilocybin mushroom species most common on the black market as a street drug.

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

Psilocybin mushrooms, commonly known as magic mushrooms, are a polyphyletic informal group of fungi that contain psilocybin which turns into psilocin upon ingestion. Biological genera containing psilocybin mushrooms include Psilocybe, Panaeolus, Inocybe, Pluteus, Gymnopilus, and Pholiotina. Psilocybin mushrooms have been and continue to be used in indigenous New World cultures in religious, divinatory, or spiritual contexts. They are also used as recreational drugs. They may be depicted in Stone Age rock art in Africa and Europe, but are most famously represented in the Pre-Columbian sculptures and glyphs seen throughout North, Central and South America.

<span class="mw-page-title-main">4-HO-DiPT</span> Chemical compound

4-Hydroxy-N,N-diisopropyltryptamine is a synthetic psychedelic drug. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT and has a tryptamine molecular sub-structure.

<span class="mw-page-title-main">Psilocin</span> Psychedelic substance

Psilocin is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. Acting on the 5-HT2A receptors, psilocin modulates the production and reuptake of serotonin. The mind-altering effects of psilocin are highly variable and subjective and resemble those of LSD and DMT.

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

Diisopropyltryptamine is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily aural.

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

DET, also known under its chemical name N,N-diethyltryptamine and as T-9, is a psychedelic drug closely related to DMT and 4-HO-DET. However, despite its structural similarity to DMT, its activity is induced by an oral dose of around 50–100 mg, without the aid of MAO inhibitors, and the effects last for about 2–4 hours.

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

Baeocystin is a zwitterionic alkaloid and analog of psilocybin. It is found as a minor compound in most psilocybin mushrooms together with psilocybin, norbaeocystin, aeruginascin, and psilocin. 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.

<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.

<span class="mw-page-title-main">5-MeO-DET</span> Chemical compound

5-MeO-DET or 5-methoxy-N,N-diethyltryptamine is a hallucinogenic tryptamine.

<span class="mw-page-title-main">4-HO-MiPT</span> Chemical compound

4-HO-MiPT is a synthetic substituted aromatic compound and a lesser-known psychedelic tryptamine. It is thought to be a serotonergic psychedelic, similar to magic mushrooms, LSD and mescaline. Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine psilocin, which is the primary psychoactive chemical in magic mushrooms.

<i>O</i>-Acetylpsilocin Chemical compound

O-Acetylpsilocin is a semi-synthetic psychoactive drug that has been suggested by David Nichols to be a potentially useful alternative to psilocybin for pharmacological studies, as they are both believed to be prodrugs of psilocin. However, some users report that O-acetylpsilocin's subjective effects differ from those of psilocybin and psilocin. Additionally, some users prefer 4-AcO-DMT to natural psilocybin mushrooms due to feeling fewer adverse side effects such as nausea and heavy body load, which are more frequently reported in experiences involving natural mushrooms. It is the acetylated form of the psilocybin mushroom alkaloid psilocin and is a lower homolog of 4-AcO-MET, 4-AcO-DET, 4-AcO-MiPT and 4-AcO-DiPT.

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

Ethocybin is a homologue of the mushroom alkaloid psilocybin, and a semi-synthetic psychedelic alkaloid of the tryptamine family. Effects of ethocybin are comparable to those of a shorter LSD or psilocybin trip, although intensity and duration vary depending on dosage, individual physiology, and set and setting.

<span class="mw-page-title-main">4-HO-MET</span> Chemical compound

4-HO-MET, is a lesser-known psychedelic drug. It is a structural− and functional analog of psilocin as well as the 4-hydroxyl analog of methylethyltryptamine (MET). 4-HO-MET was first synthesized by Alexander Shulgin. In his book TiHKAL, the dosage is listed as 10-20 mg. 4-HO-MET produces psilocin-like distortion of color, sound, and form. Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-HO-MET. There have been no reports of deaths from 4-HO-MET, even though people have reported taking doses up to 150 mg, more than an order of magnitude above the effective dose.

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

Aeruginascin or N,N,N-trimethyl-4-phosphoryloxytryptamine is an indoleamine derivative which occurs naturally within the mushrooms Inocybe aeruginascens and Pholiotina cyanopus, and Psilocybe cubensis. Aeruginascin is the N-trimethyl analogue of psilocybin. It is closely related to the frog skin toxin bufotenidine (5-HTQ), a potent 5-HT3 receptor agonist, but the aeruginascin metabolite 4-HO-TMT shows strong binding at the 5-HT2 receptors similar to psilocin. 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 experiences. This is in contrast to the slight and in some cases extremely dysphoric experiences reported from the accidental ingestion of non aeruginascin containing mushrooms (containing solely psilocybin and psilocin).

Psilocybe indica is a species of mushroom in the family Hymenogastraceae. The mushroom contains psilocybin, a prodrug for the psychedelic tryptamine psilocin.

<span class="mw-page-title-main">4-HO-αMT</span> Chemical compound

4-Hydroxy-α-methyltryptamine (4-HO-αMT) is a psychedelic drug of the tryptamine class. It is a close structural analogue of α-methyltryptamine (αMT) and produces similar effects to it, but with exacerbated side effects similarly to 5-MeO-αMT. Alexander Shulgin describes 4-HO-αMT briefly in his book TiHKAL:

The 4-hydroxy analogue of αMT has been looked at in human subjects. It is reported to be markedly visual in its effects, with some subjects reporting dizziness and a depressed feeling. There were, however, several toxic signs at doses of 15 to 20 milligrams orally, including abdominal pain, tachycardia, increased blood pressure and, with several people, headache and diarrhea.

<span class="mw-page-title-main">4-MeO-DMT</span> Chemical compound

4-MeO-DMT (4-methoxy-N,N-dimethyltryptamine) is a tryptamine derivative which has some central activity in animal tests similar to that of related psychedelic tryptamine drugs, although with significantly lower potency than either 5-MeO-DMT or 4-hydroxy-DMT (psilocin).


  1. Julia M, Manoury P, Voillaume MC (1965). "[No 209 - Recherches en série indolique. XIV (*) - Sur des méthoxy-5 hydroxy-4, méthoxy-5 hydroxy-6 et méthoxy-7 hydroxy-6 tryptamines]". Bull Chim Soc Fr (in French): 1417–23.
  2. "Ask Dr. Shulgin Online: 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine, Psilocybe mushrooms, Psilocin" . Retrieved 2023-04-29.
  3. Gartz J (1989). "Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe". Journal of Basic Microbiology. 29 (6): 347–52. doi:10.1002/jobm.3620290608. PMID   2614674. S2CID   43308695.
  4. "PSILOMETHOXIN Trademark of Church of the Sacred Synthesis - Serial Number 97342001 - Alter".
  5. "Church of Psilomethoxin".
  6. Companies
  7. "PSILOMETHOXIN Trademark of Church of the Sacred Synthesis - Serial Number 97342001 - Alter".
  8. Williamson, Samuel; Sherwood, Alexander (12 April 2023). "Fungi Fiction: Analytical Investigation into the Church Of Psilomethoxin's Alleged Novel Compound Using UPLC-HRMS". American Chemical Society (ACS). doi:10.26434/chemrxiv-2023-bxxtl.
  9. "Letter from CEO". Promega Corp.
  10. "Bill Linton President". Usona Institute.
  11. Psychedelic capitalism Archived 13 April 2023 at the Wayback Machine