:4-MeO-DMT

{{Short description|Chemical compound}}

{{Use dmy dates|date=April 2023}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477222469

| IUPAC_name = 2-(4-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine

| image = 4-MeO-DMT.png

| image2 = 4-MeO-DMT 3D BS.png

| tradename =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 3965-97-7

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

| UNII = X4NBI2F334

| PubChem = 12017578

| IUPHAR_ligand =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 23126449

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 32029

| C=13 | H=18 | N=2 | O=1

| smiles = CN(C)CCC1=CNC2=CC=CC(OC)=C21

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C13H18N2O/c1-15(2)8-7-10-9-14-11-5-4-6-12(16-3)13(10)11/h4-6,9,14H,7-8H2,1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HFYHBTWTJDAYGW-UHFFFAOYSA-N

}}

4-MeO-DMT (4-methoxy-N,N-dimethyltryptamine or O-Methylpsilocin) is a tryptamine derivative which has some psychoactive activity in animal tests similar to that of the related psychedelic tryptamine drug psilocin, although with significantly lower potency than either 5-MeO-DMT or 4-hydroxy-DMT (psilocin) itself.{{cite journal |vauthors =Glennon RA, Young R, Benington F, Morin RD |title=Hallucinogens as discriminative stimuli: a comparison of 4-OMe DMT and 5-OMe DMT with their methythio counterparts |journal=Life Sciences |volume=30 |issue=5 |pages=465–7 |date=February 1982 |pmid=6801410 |doi= 10.1016/0024-3205(82)90463-5}}{{cite journal |vauthors =Kline TB, Benington F, Morin RD, Beaton JM |title=Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety |journal=Journal of Medicinal Chemistry |volume=25 |issue=8 |pages=908–13 |date=August 1982 |pmid=7120280 |doi= 10.1021/jm00350a005}}{{cite journal |vauthors =Kline TB, Benington F, Morin RD, Beaton JM, Glennon RA, Domelsmith LN, Houk KN, Rozeboom MD |title=Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives |journal=Journal of Medicinal Chemistry |volume=25 |issue=11 |pages=1381–3 |date=November 1982 |pmid=6815326 |doi= 10.1021/jm00353a021}}{{cite book | vauthors = Nichols DE, Glennon RA | date = 1984 | chapter = Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens | veditors = Jacobs BL | title = Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives | pages = 95–142 | publisher = Raven Press | location = New York | isbn = 978-0-89004-990-7 | oclc = 10324237 | url = https://books.google.com/books?id=EdpsAAAAMAAJ&pg=PA95 | chapter-url = https://bitnest.netfirms.com/external/Books/HallucinogensNBCP95 }}