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5-Ethoxy-DMT

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5-Ethoxy-DMT
Clinical data
Other names5-EtO-DMT; 5-Ethoxy-N,N-dimethyltryptamine; O-Ethylbufotenine; O-Ethylbufotenin
Identifiers
  • 2-(5-ethoxy-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H20N2O
Molar mass232.327 g·mol−1
3D model (JSmol)
  • CCOc(cc12)ccc1[nH]cc2CCN(C)C
  • InChI=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 checkY
  • Key:OSUDCFCSUHGWJF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.[1]

Chemistry

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Analogues

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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.[2] 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.[2]

See also

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References

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  1. ^ Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "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. ^ a b Tearavarich R, Hahnvajanawong V, Dempster N, Daley PF, Cozzi NV, Brandt SD (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. 3 (9): 597–608. doi:10.1002/dta.223. PMID 21960544.
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