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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.
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 DET into 4-HO-DET and 4-PO-DET, both of which had never before been found in nature.
In the case of DET the mushrooms yielded only 4-HO-DET or 4-PO-DET respectively, instead of psilocin (4-HO-DMT) and psilocybin (4-PO-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 might also be considered illegal.
Theoretically, this method would 4-hydroxylate and 4-phosphoryloxylate any tryptamine added to the substrate, opening the possibility of synthesizing as yet undiscovered tryptamines.
- Julia M, Manoury P, Voillaume M C (1965). "[No 209 - Recherches en série indolique. XIV (*) - Sur des méthoxy-5 hydroxy-4, méthoxy-5 hydroxy-6 et méthoxy-7 hydroxy-6 tryptamines]". Bull Chim Soc Fr (in French): 1417–23.
- Gartz J (1989). "Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe". J. Basic Microbiol. 29 (6): 347–52. doi:10.1002/jobm.3620290608. PMID 2614674.