5-Chloro-DMT

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

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

| image = 5-Chloro-DMT.svg

| width =

| tradename =

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

| CAS_number = 22120-32-7

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

| UNII = S62WYB8S7C

| PubChem = 2762739

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

| ChemSpiderID = 2043437

| ChEMBL =

| synonyms = 5-Chloro-N,N-dimethyltryptamine; 5-Chloro-DMT; 5-Cl-DMT

| C=12 | H=15 | Cl=1 | N=2

| smiles = CN(C)CCC1=CNC2=C1C=C(C=C2)Cl

| StdInChI = 1S/C12H15ClN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3

| StdInChIKey = BXYDWQABVPBLBU-UHFFFAOYSA-N

}}

5-Chloro-N,N-dimethyltryptamine (5-chloro-DMT or 5-Cl-DMT) is a tryptamine derivative related to compounds such as 5-bromo-DMT and 5-fluoro-DMT. It acts as a serotonin receptor agonist and has primarily sedative effects in animal studies.{{cite journal | vauthors = Benington F, Morin RD, Clark LC | title = Synthesis of some 5- and 6-chloro, 5-methyl, and 5,6,7-trimethyl derivatives of tryptamine. | journal = Journal of Organic Chemistry | date = September 1960 | volume = 25 | issue = 9 | pages = 1542–1547 | doi = 10.1021/jo01079a020 }}{{cite journal | vauthors = Ibrahim MA, El-Alfy AT, Ezel K, Radwan MO, Shilabin AG, Kochanowska-Karamyan AJ, Abd-Alla HI, Otsuka M, Hamann MT | title = Marine Inspired 2-(5-Halo-1H-indol-3-yl)-N,N-dimethylethanamines as Modulators of Serotonin Receptors: An Example Illustrating the Power of Bromine as Part of the Uniquely Marine Chemical Space | journal = Marine Drugs | volume = 15 | issue = 8 | date = August 2017 | page = 248 | pmid = 28792478 | pmc = 5577603 | doi = 10.3390/md15080248 | doi-access = free }}{{cite journal | vauthors = Dong C, Ly C, Dunlap LE, Vargas MV, Sun J, Hwang IW, Azinfar A, Oh WC, Wetsel WC, Olson DE, Tian L | title = Psychedelic-inspired drug discovery using an engineered biosensor | journal = Cell | volume = 184 | issue = 10 | pages = 2779–2792.e18 | date = May 2021 | pmid = 33915107 | doi = 10.1016/j.cell.2021.03.043 | pmc = 8122087 }} It is known to have affinity for and to act as an agonist of the serotonin 5-HT_1A, 5-HT_2A, and 5-HT_2C receptors.{{cite journal | vauthors = Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI | title = Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter | journal = J Pharmacol Exp Ther | volume = 385 | issue = 1 | pages = 62–75 | date = April 2023 | pmid = 36669875 | pmc = 10029822 | doi = 10.1124/jpet.122.001454 | url = https://pmc.ncbi.nlm.nih.gov/articles/PMC10029822/pdf/jpet.122.001454.pdf}}{{cite journal | vauthors = Chen X, Li J, Yu L, Maule F, Chang L, Gallant JA, Press DJ, Raithatha SA, Hagel JM, Facchini PJ | title = A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines | journal = J Biol Chem | volume = 299 | issue = 10 | pages = 105231 | date = October 2023 | pmid = 37690691 | pmc = 10570959 | doi = 10.1016/j.jbc.2023.105231 | url = }}{{cite | vauthors = Chen X, Li J, Yu L, Dhananjaya D, Maule F, Cook S, Chang L, Gallant J, Press D, Bains JS, Raithatha S, Hagel J, Facchini P | title=Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery | date=10 March 2023 | doi=10.21203/rs.3.rs-2667175/v1 | doi-access=free | url=https://www.researchsquare.com/article/rs-2667175/latest.pdf | access-date=18 March 2025 | page=}} The compound has been sold as a designer drug.{{cite web | url = https://www.policija.si/apps/nfl_response_web/0_Analytical_Reports_final/5-Cl-DMT-ID-2175-20_report.pdf | title = Analytical Report: 5-Cl-DMT. | publisher = Nacionalni Forenzični Laboratorij | location = Slovenia | date = July 2020 }}