1-Methyl-DMT

vanc 6 1-Methyl-DMT.svg skin-invert-image 200px 1-TMT 3D.png bg-transparent 225px Serotonin receptor modulator; Psychoplastogen None 13366-47-7 25927 24156 2036916 1-Me-DMT; 1-Methyl-N,N-dimethyltryptamine; 1,N,N-Timethyltryptamine; 1,N,N-TMT; 1-TMT; N,N,1-Trimethyltryptamine N,N-dimethyl-2-(1-methylindol-3-yl)ethanamine 13 18 2 CN1C=C(C2=CC=CC=C21)CCN(C)C 1S/C13H18N2/c1-14(2)9-8-11-10-15(3)13-7-5-4-6-12(11)13/h4-7,10H,8-9H2,1-3H3 WYFWKMQPMCPKLZ-UHFFFAOYSA-N 1-Methyl-DMT, or 1-Me-DMT, also known as 1-methyl-N,N-dimethyltryptamine or as 1,N,N-trimethyltryptamine (1,N,N-TMT or 1-TMT), is a serotonin receptor modulator of the tryptamine family related to dimethyltryptamine (DMT) and lespedamine (1-methoxy-DMT). 1-Methyl-DMT https://isomerdesign.com/pihkal/read/tk/6#5111 "Several simple substitution derivatives of DMT are known. Those that are known to be psychedelic have their own recipes, of course, but the others will be summarized here. The 1-methyl homologue of DMT (1,N,N-trimethyltryptamine) can be prepared from DMT in KOH and DMSO, with CH3I. It forms a picrate salt which melts at 175–179 °C, and bioxalate, mp 174–176 °C. It is more toxic than DMT in rats, but has an identical serotonin binding capacity. The compound with a methoxy group substituent at the 1-position is called Lespedamine, 1-MeO-DMT." Pharmacology Pharmacodynamics 1-Methyl-DMT appears to have similar affinity for serotonin receptors as DMT, but is more toxic than DMT in rodents. Glennon RA, Gessner PK Serotonin receptor binding affinities of tryptamine analogues Journal of Medicinal Chemistry 22 4 428–432 April 1979 430481 10.1021/jm00190a014 Glennon RA, Young R, Rosecrans JA, Kallman MJ Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities Psychopharmacology 68 2 155–158 1980 6776558 10.1007/BF00432133 In another study, it showed 3-fold higher affinity for the serotonin 5-HT2A receptor than DMT. Lyon RA, Titeler M, Seggel MR, Glennon RA Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens European Journal of Pharmacology 145 3 291–297 January 1988 3350047 10.1016/0014-2999(88)90432-3 Glennon RA, Seggel MR Interaction of Phenylisopropylamines with Central 5-HT2 Receptors Probing Bioactive Mechanisms ACS Symposium Series 413 264–280 14 November 1989 10.1021/bk-1989-0413.ch018 American Chemical Society Washington, DC 978-0-8412-1702-7 https://pubs.acs.org/doi/book/10.1021/bk-1989-0413.ch018 In a further study, it showed abolished affinity for the 5-HT1E receptor and 30-fold lower affinity for the serotonin 5-HT1F receptor than DMT. Klein MT, Dukat M, Glennon RA, Teitler M Toward selective drug development for the human 5-hydroxytryptamine 1E receptor: a comparison of 5-hydroxytryptamine 1E and 1F receptor structure-affinity relationships The Journal of Pharmacology and Experimental Therapeutics 337 3 860–867 June 2011 21422162 3101003 10.1124/jpet.111.179606 1-Methyl-DMT shows comparable psychoplastogenic effects in preclinical research to DMT. Dunlap LE, Azinfar A, Ly C, Cameron LP, Viswanathan J, Tombari RJ, Myers-Turnbull D, Taylor JC, Grodzki AC, Lein PJ, Kokel D, Olson DE Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies Journal of Medicinal Chemistry 63 3 1142–1155 February 2020 31977208 7075704 10.1021/acs.jmedchem.9b01404 Dong C, Ly C, Dunlap LE, Vargas MV, Sun J, Hwang IW, Azinfar A, Oh WC, Wetsel WC, Olson DE, Tian L Psychedelic-inspired drug discovery using an engineered biosensor Cell 184 10 2779–2792.e18 May 2021 33915107 8122087 10.1016/j.cell.2021.03.043 Chemistry Synthesis The chemical synthesis of 1-methyl-DMT has been described. Analogues Analogues of 1-methyl-DMT include dimethyltryptamine (DMT), 1-methyltryptamine, lespedamine (1-MeO-DMT), 1-benzoyl-DMT, 1-methylpsilocin (1-Me-4-HO-DMT; CMY-16), 2-methyl-DMT, 4-methyl-DMT, 5-methyl-DMT, 6-methyl-DMT, and 7-methyl-DMT, among others. History The drug was briefly mentioned by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved). 1-Methyl-DMT was first described in the scientific literature by Richard Glennon and colleagues in 1979. See also Substituted tryptamine References External links 1-Methyl-DMT - Isomer Design Category:1-Alkyltryptamines Category:N,N-Dialkyltryptamines Category:Dimethylamino compounds Category:Psychoplastogens Category:Serotonin receptor modulators