1-Propyl-5-MeO-AMT

vanc 6 1-Propyl-5-MeO-AMT structure.svg skin-invert-image 225px Serotonin receptor modulator; Serotonin 5-HT2A receptor modulator 14739627 23182714 439773 1-Propyl-5-MeO-DMT; 1-Pr-5-MeO-DMT; 1-Propyl-5-methoxy-α-methyltryptamine; N1-n-Propyl-5-methoxy-α-methyltryptamine 1-(5-methoxy-1-propylindol-3-yl)propan-2-amine 15 22 2 1 CCCN1C=C(C2=C1C=CC(=C2)OC)CC(C)N 1S/C15H22N2O/c1-4-7-17-10-12(8-11(2)16)14-9-13(18-3)5-6-15(14)17/h5-6,9-11H,4,7-8,16H2,1-3H3 DAGLCFOMYRIMJJ-UHFFFAOYSA-N 1-Propyl-5-MeO-AMT, also known as 1-propyl-5-methoxy-α-methyltryptamine, is a serotonin receptor modulator of the tryptamine, α-alkyltryptamine, and 5-methoxytryptamine families. Araújo AM, Carvalho F, Bastos M, Guedes de Pinho P, Carvalho M The hallucinogenic world of tryptamines: an updated review Archives of Toxicology 89 8 1151–1173 August 2015 25877327 10.1007/s00204-015-1513-x 2015ArTox..89.1151A Like phenylalkylamines, the tryptamine hallucinogens such as LSD, psilocin, DMT or 5-MeO-DMT act as 5-HT2 receptor agonists, but they are much less selective, binding to a variety of 5-HT1 and 5-HT2 receptor subtypes (including 5-HT1A, 5-HT1B, 5-HT1C, 5-HT2A and 5-HT2C receptors) with different affinities (Blair et al. 2000; Fantegrossi et al. 2006, 2008a; McKenna et al. 1990; Peden et al. 1981; Strassman et al. 1996; Winter et al. 2000). For example, N1-n-propyl-5-methoxyα-methyltryptamine binds preferentially at 5-HT2 receptors (Glennon et al. 1990), while 5-MeO-DIPT has a considerably increased affinity for 5-HT1A receptors, although it also has affinity for 5-HT2A and 5-HT2C receptors (Fantegrossi et al. 2006). Vangveravong S Synthesis of trans-2-(indol-3-yl)cyclopropylamines: Rigid tryptamine analogues 1994 ProQuest https://www.proquest.com/docview/304131663 22 March 2025 304131663 For example, 1-n-propyl-5-methoxy-α-methyltryptamine binds with significant affinity and selectivity at the 5-HT2 receptor relative to other 5-HT receptors.76 [...] 76. Glennon. R. A.; Chaurasia, Titeler, M. Binding of Indolylalkylamines at 5-HT Serotonin Receptors: Examination of a Hydrophobic Binding Region. J. Med. Chen 1990, 33, 2777-2784. Glennon RA, Chaurasia C, Titeler M Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region Journal of Medicinal Chemistry 33 10 2777–2784 October 1990 2213830 10.1021/jm00172a016 Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-α-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki > 10000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date. It is the 1-propyl derivative of 5-methoxy-α-methyltryptamine (5-MeO-AMT). Whereas most tryptamines are highly non-selective in terms of binding to serotonin receptors, 1-propyl-5-MeO-AMT shows selectivity for the serotonin 5-HT2A receptor. Its affinities (Ki) for serotonin receptors were 12nM for the serotonin 5-HT2A receptor, 120nM for the serotonin 5-HT2C receptor, 5,000nM for the serotonin 5-HT1B receptor, 7,100nM for the serotonin 5-HT1A receptor, and >10,000nM for the serotonin 5-HT1D receptor, whereas other serotonin receptors were not reported. Its capacity and potency in activating the serotonin receptors was also not reported. The drug was developed by Richard Glennon and colleagues and was first described in 1990. At the time, it was described as the most 5-HT2A receptor-selective tryptamine known to date. See also 1-Methyltryptamine 1-Methylpsilocin (1-methyl-4-HO-DMT) Lespedamine (1-methoxy-DMT) O-4310 (1-isopropyl-6-fluoro-4-HO-DMT) MLD-41 (1-methyl-LSD) Methysergide (1-methylmethylergometrine) References External links 1-Propyl-5-MeO-AMT - Isomer Design Category:1-Alkyltryptamines Category:Alpha-Alkyltryptamines Category:5-Methoxytryptamines Category:Propyl compounds Category:Serotonin receptor modulators