5-Ethoxy-DMT

From Wikipedia, the free encyclopedia
Jump to: navigation, search
5-Ethoxy-DMT
5-EtO-DMT structure.png
Systematic (IUPAC) name
2-(5-ethoxy-1H-indol-3-yl)-N,N-dimethylethanamine
Clinical data
Legal status ?
Identifiers
CAS number 855245-09-9 N
ATC code ?
ChemSpider 26286732 YesY
Chemical data
Formula C14H20N2O 
Mol. mass 232.321 g/mol
 N (what is this?)  (verify)

5-Ethoxy-N,N-dimethyltryptamine (5-EtO-DMT, O-Ethylbufotenine) is a tryptamine derivative, which has been previously synthesised as a chemical intermediate, but has not been studied to determine its pharmacology.[1] Some closely related compounds have been studied and found to act as agonists at the 5-HT1A and 5-HT1D serotonin receptors, with increasing selectivity for 5-HT1D as the 5-alkoxy chain is lengthened, but generally reduced affinity with N,N-dialkylation.[2] The affinity of larger 5-position substituted N,N-dialkyltryptamines at the 5-HT2 receptor subtypes has in most cases not been studied, but the widespread recreational use of N,N-dialkylated 5-methoxytryptamine derivatives 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, and consequently not only 5-EtO-DMT but also 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, were synthesised as analytical standards in order to facilitate future research into these compounds.[3]

See also[edit]

References[edit]

  1. ^ TIHKAL #19
  2. ^ Glennon RA, Hong SS, Bondarev M, Law H, Dukat M, Rakhi S, Power P, Fan E, Kinneau D, Kamboj R, Teitler M, Herrick-Davis K, Smith C (January 1996). "Binding of O-alkyl derivatives of serotonin at human 5-HT1D beta receptors". Journal of Medicinal Chemistry 39 (1): 314–22. doi:10.1021/jm950498t. PMID 8568822. 
  3. ^ Tearavarich, Ruchanok; Hahnvajanawong, Viwat; Dempster, Nicola; Daley, Paul F.; Cozzi, Nicholas V.; Brandt, Simon D. (2010). "Microwave-accelerated preparation and analytical characterization of 5-ethoxy-N,N-dialkyl-[α,α,β,β-H4]- and [α,α,β,β-D4]-tryptamines". Drug Testing and Analysis: n/a–n/a. doi:10.1002/dta.223.  edit