4-Hydroxy-5-methoxydimethyltryptamine

Identifiers
IUPAC name 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine
CAS Number	2433-31-0 N
ChemSpider	21106242 Y
UNII	DZ7JH6CVB7
Chemical and physical data
Formula	C13H18N2O2
Molar mass	234.299 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN(C)CCc2c[nH]c1ccc(OC)c(O)c12
InChI 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 Y Key:YTBHRCRBKLRGBT-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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]

Legality

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]