4-Hydroxy-5-methoxydimethyltryptamine explained

4-Hydroxy-5-methoxydimethyltryptamine, also known as 4-HO-5-MeO-DMT or psilomethoxin, is a hypothetical novel psychedelic drug.

It is structurally similar to other psychedelic tryptamines, but very little is known about its effects. 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. Alexander Shulgin hypothesized that 4-HO-5-MeO-DMT could be biosynthesized by feeding Psilocybe cultures with 5-MeO-DMT, referencing a 1988 study by Jochen Gartz where transformation of DET into 4-HO-DET and 4-PO-DET was reported using such a method, with neither compounds having ever been found in nature.^{[2] [3]}

Notes and References

1. Julia M, Manoury P, Voillaume MC . No 209 - Recherches en série indolique. XIV (*) - Sur des méthoxy-5 hydroxy-4, méthoxy-5 hydroxy-6 et méthoxy-7 hydroxy-6 tryptamines . fr . Bulletin de la Société Chimique de France . 1417–1423 . 1965 .
2. Web site: Ask Dr. Shulgin Online . 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine, Psilocybe mushrooms, Psilocin . 2023-04-29 . en.
3. Gartz J . Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe . Journal of Basic Microbiology . 29 . 6 . 347–352 . 1989 . 2614674 . 10.1002/jobm.3620290608 . 43308695 .