1Z2MAP1O

vanc 6 1Z2MAP1O chemical structure.svg skin-invert-image 175px 1Z2MAP1O 3D.png bg-transparent 225px Monoamine releasing agent; Serotonin 5-HT1B receptor agonist; Serotonin 5-HT2B receptor antagonist; Entactogen None 2110204-31-2 165756415 26962386 1-(Indolizin-3-yl)-2-(methylamino)propan-1-one; Structure XLX; Indolizine-BK-NM-AMT 1-indolizin-3-yl-2-(methylamino)propan-1-one 12 14 2 1 CC(C(=O)C1=CC=C2N1C=CC=C2)NC 1S/C12H14N2O/c1-9(13-2)12(15)11-7-6-10-5-3-4-8-14(10)11/h3-9,13H,1-2H3 BFSFBVDVCJVAMW-UHFFFAOYSA-N 1Z2MAP1O, also known as 1-(indolizin-3-yl)-2-(methylamino)propan-1-one, is a monoamine releasing agent and serotonin receptor modulator of the indolizinylethylamine family.WO 2023081306A1 Baggott MJ application Indolizine compounds for the treatment of mental disorders or mental enhancement 11 May 2023 3 November 2022 3 November 2022 Tactogen https://patents.google.com/patent/WO2023081306A1/ FIG. 1 depicts response curves for 1-(indolizin-3-yl)-2-(methylamino)propan-1-one (Structure XLX) in a serotonin (SERT) release assay and a dopamine (DAT) release assay. [...] EXAMPLE 11: In vitro activity assessments 1-(indolizin-3-yl)-2-(methylamino)propan-1-one (Structure XLX) was evaluated for activity at 47 target sites at ten concentrations up to 30 μM, with EC50 or IC50 determined whenever possible. Activity was detected only at 5-HT1B (agonist effects with an EC50 of 1.13 μM) and 5-HT2B (antagonist effects with an IC50 of 2.14 μM) receptors and at DAT (IC50 of 2.41 μM) and NET (IC50 of 5.69 μM). [...] EXAMPLE 12: Human Monoamine Transporter (hMAT) Release Assays [...] To assess the effects of indolizine derivatives on extracellular dopamine and serotonin concentrations, in vitro measures of serotonin and dopamine release were made using Chinese hamster ovary cells that stably expressed human monoamine transporters, dopamine (hDAT) and serotonin (hSERT) transporter. Dextroamphetamine and norfenfluramine were used as reference releasers of dopamine and serotonin, respectively. [...] Assay results revealed that 1-(indolizin-3-yl)-2-(methylamino)propan-1-one was more potent at releasing DAT than 5-HT, with a DAT/SERT ratio suggesting MDMA-like effects. [...] Table 4: Effects of Structure XLX on neurotransmitter release from DAT and SERT: 1-(indolizin-3-yl)-2-(methylamino)propan-1-one: EC50 DAT (nM): 227. EC50 SERT (nM): 109. DAT/SERT ratio*: 2.1. *DAT/SERT ratios are calculated here as (DAT EC50) * /(SERT EC50) * where larger numbers indicate higher DAT selectivity hSERT release measurement methods. It is an analogue of BK-NM-AMT (β-keto-N-methyl-α-methyltryptamine) in which the indole ring has been replaced with an indolizine ring. 1Z2MAP1O has been found to be a serotonin and dopamine releasing agent as well as a weak serotonin 5-HT1B receptor agonist and serotonin 5-HT2B receptor antagonist. Conversely, its activity as a norepinephrine releasing agent was not reported, and it was inactive at the remaining sites of the 47screened targets. The drug's EC50 half-maximal effective concentration values for induction of monoamine release were 109nM for serotonin and 227nM for dopamine in Chinese hamster ovary (CHO) cells expressing the human monoamine transporters (MATs). The dopamine/serotonin ratio was 0.48. Its EC50 half-maximal effective concentration at the serotonin 5-HT1B receptor was 1,130nM, whereas its IC50 half-maximal inhibitory concentration values were 2,140nM at the serotonin 5-HT2B receptor, 2,410nM at the dopamine transporter (DAT), and 5,690nM at the norepinephrine transporter (NET). 1Z2MAP1O's inhibition of the serotonin transporter (SERT) was not reported. 1Z2MAP1O was patented by Matthew Baggott of Tactogen in 2023. See also Indolizinylethylamine Substituted tryptamine § Related compounds 2ZEDMA 1ZP2MA α-Methylisotryptamine (isoAMT) TACT411 TACT833 References External links 1Z2MAP1O - Isomer Design Category:5-HT1B agonists Category:5-HT2B antagonists Category:Experimental entactogens Category:Indolizinylethylamines Category:Ketones Category:Monoamine releasing agents Category:Secondary amines Category:Tactogen