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.

4-Hydroxy-5-methoxydimethyltryptamine
Identifiers
IUPAC name
  • 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine
CAS Number
ChemSpider
UNII
Chemical and physical data
FormulaC13H18N2O2
Molar mass234.299 g·mol−1
3D model (JSmol)
SMILES
  • CN(C)CCc2c[nH]c1ccc(OC)c(O)c12
InChI
  • InChI=1S/C13H18N2O2/c1-15(2)7-6-9-8-14-10-4-5-11(17-3)13(16)12(9)10/h4-5,8,14,16H,6-7H2,1-3H3 Y
  • Key:YTBHRCRBKLRGBT-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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 allegedly 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.

References
  1. Julia 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]". Bull Chim Soc Fr (in French): 1417–23.
  2. Gartz J (1989). "Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe". Journal of Basic Microbiology. 29 (6): 347–52. doi:10.1002/jobm.3620290608. PMID 2614674.
  3. Björklund A, Nobin A, Stenevi U (December 1973). "The use of neurotoxic dihydroxytryptamines as tools for morphological studies and localized lesioning of central indolamine neurons". Zeitschrift für Zellforschung und Mikroskopische Anatomie. 145 (4): 479–501. doi:10.1007/BF00306720. PMID 4774982. S2CID 44044588.
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