:7,N,N-TMT

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477226363

| IUPAC_name = 2-(7-methyl-1H-indol-3-yl)-N,N-dimethylethanamine

| image = 7-N,N-Trimethyltryptamine-2D-skeletal.svg

| width = 175px

| tradename =

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

| CAS_number = 65882-39-5

| PubChem = 47747

| IUPHAR_ligand =

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

| ChemSpiderID = 43445

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

| ChEMBL = 20167

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

| UNII = F9R59MT42E

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

| smiles = CC1=C(NC=C2CCN(C)C)C2=CC=C1

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

| StdInChI = 1S/C13H18N2/c1-10-5-4-6-12-11(7-8-15(2)3)9-14-13(10)12/h4-6,9,14H,7-8H2,1-3H3

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

| StdInChIKey = PQSFTUCFMWBITK-UHFFFAOYSA-N

}}

7,N,N-trimethyltryptamine (7-methyl-DMT, 7-TMT), is a tryptamine derivative which acts as an agonist of 5-HT₂ receptors.{{cite journal | vauthors = Glennon RA, Liebowitz SM, Mack EC | title = Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues | journal = Journal of Medicinal Chemistry | volume = 21 | issue = 8 | pages = 822–5 | date = August 1978 | pmid = 278843 | doi = 10.1021/jm00206a022 }}{{cite journal | vauthors = Glennon RA, Gessner PK | title = Serotonin receptor binding affinities of tryptamine analogues | journal = Journal of Medicinal Chemistry | volume = 22 | issue = 4 | pages = 428–32 | date = April 1979 | pmid = 430481 | doi = 10.1021/jm00190a014 }}{{cite journal | vauthors = Lyon RA, Titeler M, Seggel MR, Glennon RA | title = Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens | journal = European Journal of Pharmacology | volume = 145 | issue = 3 | pages = 291–7 | date = January 1988 | pmid = 3350047 | doi = 10.1016/0014-2999(88)90432-3 }} In animal tests, both 7-TMT and its 5-methoxy derivative 5-MeO-7-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT, but the larger 7-ethyl and 7-bromo derivatives of DMT did not produce psychedelic responses despite having higher 5-HT₂ receptor affinity in vitro (cf. DOBU, DOAM).{{cite journal | vauthors = Glennon RA, Schubert E, Jacyno JM, Rosecrans JA | title = Studies on several 7-substituted N,N-dimethyltryptamines | journal = Journal of Medicinal Chemistry | volume = 23 | issue = 11 | pages = 1222–6 | date = November 1980 | pmid = 6779006 | doi = 10.1021/jm00185a014 }} 7-TMT also weakly inhibits reuptake of serotonin but with little effect on dopamine or noradrenaline reuptake.{{cite journal | vauthors = Glennon RA, Martin B, Johnson KM, End D | title = 7,N,N-Trimethyltryptamine: a selective inhibitor of synaptosomal serotonin uptake | journal = Research Communications in Chemical Pathology and Pharmacology | volume = 19 | issue = 1 | pages = 161–4 | date = January 1978 | pmid = 625585 }}