• 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine
CAS Number
Chemical and physical data
Molar mass234.299 g·mol−1
3D model (JSmol)
  • 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
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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.

It is a psychedelic tryptamine but very little is known about it. 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. However, Alexander Shulgin has explained that it could be possible to cultivate 4-HO-5-MeO-DMT in psilocybin mushrooms by adding 5-MeO-DMT to the growing substrate of the fungus. This method was allegedly tested with 5-MeO-DMT by members of the Church of Psilomethoxin in 2021[citation needed] but not proven, and had previously been used successfully for changing DET into 4-HO-DET and 4-PO-DET, both of which had never before been found in nature.[2]


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.[3]

Religious use

Psilomethoxin is used as a religious sacrament by the Church of Psilomethoxin, created by the non-profit corporation Church of the Sacred Synthesis based in Texas.[4][5] 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."[6]


  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. ^ 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.
  3. ^ "PSILOMETHOXIN Trademark of Church of the Sacred Synthesis - Serial Number 97342001 - Alter".
  4. ^ "Church of Psilomethoxin".
  5. ^ Companies
  6. ^ "PSILOMETHOXIN Trademark of Church of the Sacred Synthesis - Serial Number 97342001 - Alter".