4-Hydroxy-5-methoxydimethyltryptamine

Summary

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.

4-Hydroxy-5-methoxy-N,N-dimethyltryptamine
Identifiers
  • 3-(2-(dimethylamino)ethyl)-5-methoxy-1H-indol-4-ol
CAS Number
  • 2433-31-0 ☒N
ChemSpider
  • 21106242 checkY
UNII
  • DZ7JH6CVB7
Chemical and physical data
FormulaC13H18N2O2
Molar mass234.299 g·mol−1
3D model (JSmol)
  • Interactive image
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)

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.