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4-Hydroxy-5-methoxydimethyltryptamine

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4-Hydroxy-5-methoxy-N,N-dimethyltryptamine
Identifiers
  • 3-(2-(dimethylamino)ethyl)-5-methoxy-1H-indol-4-ol
CAS Number
ChemSpider
UNII
Chemical and physical data
FormulaC13H18N2O2
Molar mass234.299 g·mol−1
3D model (JSmol)
Melting point146 to 147 °C (295 to 297 °F) (from ethyl acetate[1])
  • CN(C)CCc2c[nH]c1ccc(OC)c(O)c12
  • 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 checkY
  • Key:YTBHRCRBKLRGBT-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

4-Hydroxy-5-methoxydimethyltryptamine, also known as 4-HO-5-MeO-DMT or psilomethoxin, is a hypothetical novel psychedelic drug.

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

[edit]
  1. ^ a b 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". Bulletin de la Société Chimique de France (in French): 1417–1423.
  2. ^ "4-Hydroxy-5-methoxy-N,N-dimethyltryptamine, Psilocybe mushrooms, Psilocin". Ask Dr. Shulgin Online. Retrieved 2023-04-29.
  3. ^ Gartz J (1989). "Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe". Journal of Basic Microbiology. 29 (6): 347–352. doi:10.1002/jobm.3620290608. PMID 2614674. S2CID 43308695.


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