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| Formula | C13H18N2O2 |
| Molar mass | 234.299 g·mol−1 |
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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 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.[2]
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,[3] there is some concern that this compound may share that neurotoxicity, though this has not been investigated.