4-Hydroxy-5-methoxydimethyltryptamine

4-Hydroxy-5-methoxydimethyltryptamine, or 4-HO-5-MeO-DMT, is the 4-hydroxy counterpart of 5-MeO-DMT, or the 5-methoxy counterpart of psilocin.

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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] They only reported the synthesis and physical properties of the compound and it has never been documented or explored in any other way.

Their paper cites 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. Though this method has never been explored with 5-MeO-DMT, it has been used successfully for changing DPT and DIPT into 4-HO-DPT and 4-HO-DIPT, both of which had never before been found in nature.

In the cases of DPT and DiPT the mushrooms yielded only 4-HO-DPT or 4-HO-DiPT respectively, instead of psilocin (4-HO-DMT), suggesting that the presence of the extraneous N-dialkylated tryptamines competed for the enzymes in the fungus mycelium that would normally produce psilocin. This method thus not only produced new chemical compounds that had never previously been made synthetically, but also rendered the fungus itself completely legal in many countries because of its absence of psilocin or psilocybin, although in countries with stricter drug analogue laws such as the USA or Australia the novel tryptamines produced would also be illegal.

The same process can also be used to make psilocin bearing mushrooms of much higher potency than normal by adding small quantities of DMT to the substrate, to act as feedstock for the production of psilocin. However the amount of DMT added must be carefully controlled, as if too much is added it appears to inhibit the action of the enzyme.

Theoretically, this method would 4-hydroxylate any tryptamine added to the substrate, opening the possibility of synthesizing as yet undiscovered tryptamines. It is unclear whether longer incubation times would allow the action of the second enzyme in the process (which normally phosphorylates psilocin into psilocybin), to produce 4-phosphorylated analogues of the tryptamines, such as e.g. 4-PO-DPT or 4-PO-DiPT.

References

1. ^ Julia M, Melamed R, Gombert R. Research on the indole series. XVI. On aryl-2-tryptamines and homologous amines. Annales de l'Institut Pasteur (Paris). 1965 Sep;109(3):343-62.