4-Hydroxy-5-methoxydimethyltryptamine

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
4-Hydroxy-5-methoxy-N,N-dimethyltryptamine
Identifiers
  • 3-[2-(Dimethylamino)ethyl]-5-methoxy-1H-indol-4-ol
CAS Number
ChemSpider
UNII
Chemical and physical data
FormulaC13H18N2O2
Molar mass234.299 g·mol−1
3D model (JSmol)
Melting point146 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 checkY
  • Key:YTBHRCRBKLRGBT-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

Legality

In the United States, 4-HO-5-MeO-DMT may not be considered illegal under the Federal Analogue Act if sold or used for consumption due to significant structural differences from tryptamines with a single indolic substitution, which comprise most analogous compounds 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]

References
  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
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