5-Ethoxy-DMT

5-Ethoxy-DMT
Identifiers
	IUPAC name 2-(5-ethoxy-1H-indol-3-yl)-N,N-dimethylethanamine;
CAS Number	855245-09-9 ;
ChemSpider	26286732 ;
CompTox Dashboard (EPA)	DTXSID70726745 ;
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.321 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOc(cc12)ccc1ncc2CCN(C)C;
	InChI 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 ; Key:OSUDCFCSUHGWJF-UHFFFAOYSA-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-HT_1A and 5-HT_1D serotonin receptors, with increasing selectivity for 5-HT_1D 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]

References

^ TIHKAL #19
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1002/dta.223, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1002/dta.223 instead.

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[1] TIHKAL #19

[pmid8568822-2] 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[3] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1002/dta.223, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1002/dta.223 instead.

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See also

References