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. 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. 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 finally tested and proven with 5-MeO-DMT by members of the Church of Psilomethoxin in 2021, 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. Manufacture, transportation, possession, and distribution of 4-HO-5-MeO-DMT in the United States may be illegal under the Federal Analogue Act due to its structural relation to psilocin, which is listed as a  Schedule I narcotic under the Controlled Substances Act of 1970. Due to the resemblance to the neurotoxin 4,5-dihydroxytryptamine, there is some concern that this compound may share that neurotoxicity, though this has not been investigated.