EMDT

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 424695163

| IUPAC_name = 2-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine

| image = EMDT structure.svg

| width =

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 263744-72-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = GWM65988LJ

| ATC_prefix = none

| ATC_suffix =

| PubChem = 6918513

| IUPHAR_ligand = 12

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 5293710

| ChEMBL = 267615

| synonyms = 2-Ethyl-5-methoxy-N,N-dimethyltryptamine; 2-Ethyl-5-MeO-DMT; 2-Et-5-MeO-DMT

| C=15 | H=22 | N=2 | O=1

| SMILES = CCc2[nH]c1ccc(OC)cc1c2CCN(C)C

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C15H22N2O/c1-5-14-12(8-9-17(2)3)13-10-11(18-4)6-7-15(13)16-14/h6-7,10,16H,5,8-9H2,1-4H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ZEYRDXUWJDGTLD-UHFFFAOYSA-N

}}

2-Ethyl-5-methoxy-N,N-dimethyltryptamine (EMDT), also known as 2-ethyl-5-MeO-DMT, is a tryptamine derivative which is used in scientific research. It acts as a selective 5-HT₆ receptor agonist, with a K_i of 16{{nbsp}}nM, and was one of the first selective agonists developed for this receptor.{{cite journal | vauthors = Glennon RA, Lee M, Rangisetty JB, Dukat M, Roth BL, Savage JE, McBride A, Rauser L, Hufeisen S, Lee DK | display-authors = 6 | title = 2-Substituted tryptamines: agents with selectivity for 5-HT(6) serotonin receptors | journal = Journal of Medicinal Chemistry | volume = 43 | issue = 5 | pages = 1011–1018 | date = March 2000 | pmid = 10715164 | doi = 10.1021/jm990550b | author5-link = Bryan Roth }}{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | pages = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | doi-access = free | bibcode = 2010PLoSO...5.9019R | url = }} Its affinities for many other targets have also been reported. EMDT inhibits both short- and long-term memory formation in animal studies, and this effect can be reversed by the selective 5-HT₆ antagonist SB-399,885.{{cite journal | vauthors = Meneses A, Perez-Garcia G, Liy-Salmeron G, Flores-Galvez D, Castillo C, Castillo E | title = The effects of the 5-HT(6) receptor agonist EMD and the 5-HT(7) receptor agonist AS19 on memory formation | journal = Behavioural Brain Research | volume = 195 | issue = 1 | pages = 112–119 | date = December 2008 | pmid = 18191236 | doi = 10.1016/j.bbr.2007.11.023 | s2cid = 144901859 }} Additionally, it is active in the tail suspension test, suggesting that it could be an effective antidepressant.{{cite journal | vauthors = Svenningsson P, Tzavara ET, Qi H, Carruthers R, Witkin JM, Nomikos GG, Greengard P | title = Biochemical and behavioral evidence for antidepressant-like effects of 5-HT6 receptor stimulation | journal = The Journal of Neuroscience | volume = 27 | issue = 15 | pages = 4201–4209 | date = April 2007 | pmid = 17428998 | pmc = 6672541 | doi = 10.1523/JNEUROSCI.3110-06.2007 | doi-access = free }}