2-Methyltryptamine

vanc 6 2-Methyltryptamine.svg skin-invert-image 200px 2-MT 3D.png bg-transparent 225px Serotonin receptor agonist None 2731-06-8 75949 68452 2358910 2-MT; 2-Me-T; 2-Methyl-T 2-(2-methyl-1H-indol-3-yl)ethanamine 11 14 2 CC1=C(C2=CC=CC=C2N1)CCN 1S/C11H14N2/c1-8-9(6-7-12)10-4-2-3-5-11(10)13-8/h2-5,13H,6-7,12H2,1H3 CPVSLHQIPGTMLH-UHFFFAOYSA-N 2-Methyltryptamine (2-MT, 2-Me-T, or 2-methyl-T) is a serotonin receptor agonist of the tryptamine family. Abiero A, Ryu IS, Botanas CJ, Custodio RJ, Sayson LV, Kim M, Lee HJ, Kim HJ, Seo JW, Cho MC, Lee KW, Yoo SY, Jang CG, Lee YS, Cheong JH Four Novel Synthetic Tryptamine Analogs Induce Head-Twitch Responses and Increase 5-HTR2a in the Prefrontal Cortex in Mice Biomolecules & Therapeutics 28 1 83–91 January 2020 31230432 6939696 10.4062/biomolther.2019.049 Chen X, Li J, Yu L, Maule F, Chang L, Gallant JA, Press DJ, Raithatha SA, Hagel JM, Facchini PJ A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines The Journal of Biological Chemistry 299 10 105231 October 2023 37690691 10570959 10.1016/j.jbc.2023.105231 free Chen X, Li J, Yu L, Dhananjaya D, Maule F, Cook S, Chang L, Gallant J, Press D, Bains JS, Raithatha S, Hagel S, Facchini P Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery 10 March 2023 10.21203/rs.3.rs-2667175/v1 free https://www.researchsquare.com/article/rs-2667175/latest.pdf 17 March 2025 It shows dramatically reduced activity at serotonin receptors compared to tryptamine and mixed effects in terms of psychedelic-like effects in animals. Pharmacology Pharmacodynamics 2-MT shows affinity (Ki) for the serotonin 5-HT1A and 5-HT2A receptors, with Ki values of 1,095nM and 7,774nM, respectively. These affinities were respectively 34-fold and 3.2-fold lower than those of tryptamine in the same study. It also acts as an agonist of the serotonin 5-HT1A and 5-HT2A receptors, with EC50 half-maximal effective concentration values of 12,534nM and 4,598nM, respectively. These activational potencies were respectively 14-fold and 19-fold lower than those of tryptamine in the same study. It does not produce conditioned place preference (CPP), self-administration, or changes in locomotor activity in rodents. Findings on whether 2-MT produces the head-twitch response (HTR), a behavioral proxy of psychedelic effects, are mixed. Chen X, Li J, Yu L, Maule F, Chang L, Gallant JA, Press DJ, Raithatha SA, Hagel JM, Facchini PJ A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines The Journal of Biological Chemistry 299 10 105231 October 2023 37690691 10570959 10.1016/j.jbc.2023.105231 free In one study, it produced the HTR at a dose of 3mg/kg intraperitoneally, and this was completely blocked by the serotonin 5-HT2A receptor antagonist ketanserin. In another study, both tryptamine and 2-MT did not produce the HTR at a dose of 3mg/kg intraperitoneally. Chemistry Derivatives A number of derivatives of 2-MT are known, including: 2,α-Dimethyltryptamine (2,α-DMT or 2-Me-αMT) 2,N,N-Trimethyltryptamine (2,N,N-TMT or 2-Me-DMT) 2-Methyl-N,N-diethyltryptamine (2-Me-DET) 5-Methoxy-2,N,N-trimethyltryptamine (5-MeO-2,N,N-TMT or 2-Me-5-MeO-DMT) These drugs were synthesized and tested by Alexander Shulgin. He found that the drugs in this group became orally active but generally produced no or only mild psychedelic effects (with the exception of 2-Me-5-MeO-DMT). Instead, they caused effects like tactile enhancement and auditory distortion, among others. A few other derivatives, including 2-methyl-DiPT, 2-methyl-iPALT, 2-methyl-5-MeO-DALT, and 2-methyl-5-F-DALT, are also known. Klein LM, Cozzi NV, Daley PF, Brandt SD, Halberstadt AL Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs Neuropharmacology 142 231–239 November 2018 29499272 6230509 10.1016/j.neuropharm.2018.02.028 Asymmetric allyl tryptamines 20240277665A1 US 4 March 2024 https://patents.google.com/patent/US20240277665A1 Daley PF, Cozzi NV, Callaway WB Alexander Shulgin Research Institute Inc. Further derivatives of 2-MT include the following: 2-Methyl-5-HT (a moderately selective serotonin 5-HT3 receptor full agonist) 2-Methyl-5-chloro-DMT (ST-1936; a selective serotonin 5-HT6 receptor agonist) 2-Ethyl-5-methoxy-DMT (EMDT; a selective serotonin 5-HT6 receptor agonist) EMD-386088 (2-methyl-5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole) isn't technically a tryptamine but is very similar and is a serotonin 5-HT6 receptor partial agonist as well as having moderate affinity for the serotonin 5-HT3 receptor and acting as a dopamine reuptake inhibitor. Yet another related compound is 2-HO-NMT, a tryptamine alkaloid. See also Substituted tryptamine 1-Methyltryptamine 5-Methyltryptamine References External links 2-Methyl-T - Isomer Design Category:5-HT1A agonists Category:5-HT2A agonists Category:Psychedelic tryptamines Category:Aminoethyl compounds