5-Ethoxy-DMT

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Chemical compound

title: "5-Ethoxy-DMT" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["n,n-dialkyltryptamines", "dimethylamino-compounds", "ethoxy-compounds", "5-methoxytryptamines"] description: "Chemical compound" topic_path: "general/n-n-dialkyltryptamines" source: "https://en.wikipedia.org/wiki/5-Ethoxy-DMT" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 458142861 | image = 5-EtO-DMT Structure.svg | image_class = skin-invert-image | width = 225px | image2 = 5-Ethoxy-DMT 3D.png | image_class2 = bg-transparent | width2 = 200px

| tradename = | routes_of_administration = | class =

| CAS_number_Ref = | CAS_number = 855245-09-9 | PubChem = 57468316 | UNII = RXJ4TM3EX4 | IUPHAR_ligand = | ChemSpiderID_Ref = | ChemSpiderID = 26286732 | synonyms = 5-EtO-DMT; 5-Ethoxy-N,N-dimethyltryptamine; O-Ethylbufotenine; O-Ethylbufotenin

| IUPAC_name = 2-(5-ethoxy-1H-indol-3-yl)-N,N-dimethylethanamine | C=14 | H=20 | N=2 | O=1 | SMILES = CCOc(cc12)ccc1[nH]cc2CCN(C)C | StdInChI_Ref = | StdInChI = 1S/C14H20N2O/c1-4-17-12-5-6-14-13(9-12)11(10-15-14)7-8-16(2)3/h5-6,9-10,15H,4,7-8H2,1-3H3 | StdInChIKey_Ref = | StdInChIKey = OSUDCFCSUHGWJF-UHFFFAOYSA-N

5-Ethoxy-DMT, or 5-EtO-DMT, also known as 5-ethoxy-N,N-dimethyltryptamine or as O-ethylbufotenine, is a tryptamine derivative which has been previously synthesized as a chemical intermediate, but has not been studied to determine its pharmacology.

Chemistry

Analogues

Analogues of 5-EtO-DMT include bufotenin (5-HO-DMT), 5-MeO-DMT (mebufotenin), 5-EtO-AMT, 5-AlO-AMT, 5-ethyl-DMT, 5-NOT, 5-BT, and 4-AcO-DMT (O-acetylbufotenin), among others.

The widespread recreational use of 5-methoxytryptamines including 5-MeO-DMT, 5-MeO-MiPT and 5-MeO-DiPT has led to concern that the 5-ethoxy homologues of these drugs could emerge as novel designer drugs. Consequently, 5-EtO-DMT and other derivatives, including 5-EtO-DET, 5-EtO-DPT, 5-EtO-DiPT, 5-EtO-DALT, 5-EtO-MPT, 5-EtO-MiPT, 5-EtO-EiPT, 5-EtO-MET, and 5-EtO-EPT, have been synthesized as analytical standards in order to facilitate future research into these compounds.

References

References

  1. {{CiteTiHKAL "There are two structural variations of bufotenine that I feel would be interesting to explore. One deals with the ethers of the 5-hydroxyl group. The O-methyl ether is, of course, 5-MeO-DMT. It is mentioned above under the name O-methylbufotenine. What about the very obvious O-ethylbufotenine, 5-EtO-DMT? It had once been synthesized from 5-ethoxytryptophol in a physostigmine study, and had been converted to bufotenine with aluminum chloride. If the analogy from the phenethylamines applies here (MEM is as potent as TMA-2) then 5-EtO-DMT should be as potent as 5-MeO-DMT. And probably would have to be smoked for the very same reasons."
  2. (September 2011). "Microwave-accelerated preparation and analytical characterization of 5-ethoxy-N,N-dialkyl-[α,α,β,β-H(4) ]- and [α,α,β,β-D(4) ]-tryptamines". Drug Testing and Analysis.

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n,n-dialkyltryptaminesdimethylamino-compoundsethoxy-compounds5-methoxytryptamines