4-Hydroxy-5-methoxydimethyltryptamine, also known as 4-HO-5-MeO-DMT or psilomethoxin, is a hypothetical
novel psychedelic drug. It is the 4-
hydroxy counterpart of
5-MeO-DMT, or the 5-
methoxy counterpart of
psilocin.
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]
References
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abJulia M, Manoury P, Voillaume MC (1965). "No 209 - Recherches en série indolique. XIV (*) - Sur des méthoxy-5 hydroxy-4, méthoxy-5 hydroxy-6 et méthoxy-7 hydroxy-6 tryptamines". Bulletin de la Société Chimique de France (in French): 1417–1423.