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 5-MeO-DMT (5-methoxy-''N'',''N''-dimethyltryptamine) or O-methyl-bufotenin is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the Colorado R ...

, or the 5-

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

counterpart of

psilocin Psilocin (also known as 4-HO-DMT, 4-hydroxy DMT, psilocine, psilocyn, or psilotsin) is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated cou ...

. It is a psychedelic

tryptamine Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan. The chemical structure is defined by an indole ─ a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the f ...

but very little is known about it. The only report of it in the chemical literature was a paper published by

Marc Julia Marc Julia (23 October 1922 – 29 June 2010) was a French chemist and the winner of the 1990 CNRS Gold Medal in chemistry. He discovered the Julia olefination reaction in 1973. Biography Julia was born in 1922 in Paris as son of the renowned m ...

's group at the Pasteur Institute in 1965. This paper reports a 10 step synthesis of 4-HO-5-MeO-DMT from

ortho-vanillin ''ortho''-Vanillin (2-hydroxy-3-methoxybenzaldehyde) is an organic solid present in the extracts and essential oils of many plants. Its functional groups include aldehyde, ether and phenol. ''ortho''-Vanillin, a compound of the formula C8H8O3, is ...

. However, Alexander Shulgin has explained that it could be possible to cultivate 4-HO-5-MeO-DMT in

psilocybin mushrooms 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'', ''Pa ...

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 but not proven, and had previously been used successfully for changing DET into

4-HO-DET 4-HO-DET, also known as 4-hydroxy-diethyl-tryptamine, CZ-74, is a hallucinogenic drug and psychedelic compound of moderate duration. 4-HO-DET is a substituted tryptamine, structurally related to psilocin, ethocybin, and 4-HO-DIPT. Analogs The a ...

and 4-PO-DET, both of which had never before been found in nature.

Legality

In the United States, 4-HO-5-MeO-DMT may be considered illegal under the

Federal Analogue Act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed in ...

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.

Religious use

Psilomethoxin is used as a

religious Religion is usually defined as a social- cultural system of designated behaviors and practices, morals, beliefs, worldviews, texts, sanctified places, prophecies, ethics, or organizations, that generally relates humanity to supernatur ...

sacrament by the Church of Psilomethoxin, created by the non-profit corporation Church of the Sacred Synthesis based in Texas. 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."

References

External links

Ask Dr. Shulgin
{{DEFAULTSORT:Hydroxy-5-methoxydimethyltryptamine, 4- Entheogens Tryptamines Psychedelic drugs