Explore 4-MTA | PiHKAL

ChemSpider 133883
PubChem 151900
Wikidata Q230013
Erowid 4-MTA
Wikipedia 4-Methylthioamphetamine

Shulgin Index #103 MTA · Table 3Page 324Row 36

Phenethylamine: Von der Strucktur zur Funktion 4-MTA: 6.1 (8) 359 · 6.3 (33) 404, 410, 411, 419, 427 · MTA: 7.5 (167) 563

Huang, X; Marona-Lewicka, D; Nichols, DE. p-Methylthioamphetamine is a potent new non-neurotoxic serotonin-releasing agent. Eur. J. Pharmacol., 8 Dec 1992, 229 (1), 31–38. 702 kB. https://doi.org/10.1016/0014-2999(92)90282-9 #MTA

Roman, DL; Saldaña, SN; Nichols, DE; Carroll, FI; Barker, EL. Distinct molecular recognition of psychostimulants by human and Drosophila serotonin transporters. J. Pharmacol. Exp. Ther., 1 Jan 2004, 308 (2), 679–687. 519 kB. https://doi.org/10.1124/jpet.103.057836

Błachut, D; Wojtasiewicz, K; Czarnocki, Z; Szukalski, B. The analytical profile of some 4-methylthioamphetamine (4-MTA) homologues. Forensic Sci. Int., 20 Nov 2009, 192 (1–3), 98–114. 683 kB. https://doi.org/10.1016/j.forsciint.2009.08.009 #1, 4-MTA GC,MS,NMR,IR

Scorza, MC; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. https://doi.org/10.1016/S0006-2952(97)00405-X #5 MTA

Vilches-Herrera, M; Miranda-Sepúlveda, J; Rebolledo-Fuentes, M; Fierro, A; Lühr, S; Iturriaga-Vasquez, P; Cassels, BK; Reyes-Parada, M. Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors. Bioorg. Med. Chem., 15 Mar 2009, 17 (6), 2452–2460. 509 kB. https://doi.org/10.1016/j.bmc.2009.01.074 #3g NMR

Rezende, MC; Núñez, C; Sepúlveda-Boza, S; Cassels, BK; Hurtado-Guzmán, C. S-Oxidation products of alkylthioamphetamines. Synth. Commun., 1 Jan 2002, 32 (17), 2741–2750. 225 kB. https://doi.org/10.1081/SCC-120006041 #2 NMR,IR

Rodríguez, GJ; Roman, DL; White, KJ; Nichols, DE; Barker, EL. Distinct recognition of substrates by the human and Drosophila serotonin transporters. J. Pharmacol. Exp. Ther., 1 Jan 2004, 306 (1), 338–346. 452 kB. https://doi.org/10.1124/jpet.103.048751

Staack, RF; Maurer, HH. Metabolism of designer drugs of abuse. Curr. Drug Metab., 1 Jun 2005, 6 (3), 259–274. 104 kB. https://doi.org/10.2174/1389200054021825 #4-MTA

Winstock, AR; Wolff, K; Ramsey, J. 4-MTA: a new synthetic drug on the dance scene. Drug Alcohol Depend., 1 Jul 2002, 67 (2), 111–215. 102 kB. https://doi.org/10.1016/S0376-8716(02)00018-2

EMCDDA. Report on the risk assessment of 4-MTA, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, . 79 kB. #4-MTA

Cloonan, SM; Keating, JJ; Corrigan, D; O’Brien, JE; Kavanagh, PV; Williams, DC; Meegan, MJ. Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted α-alkylthioamphetamines. Bioorg. Med. Chem., 1 Jun 2010, 18 (11), 4009–4031. 1.2 MB. https://doi.org/10.1016/j.bmc.2010.04.022 #1a MS,NMR,IR

Cloonan, SM; Keating, JJ; Butler, SG; Knox, AJS; Jørgensen, AM; Peters, GH; Rai, D; Corrigan, D; Lloyd, DG; Williams, DC; Meegan, MJ. Synthesis and serotonin transporter activity of sulphur-substituted α-alkyl phenethylamines as a new class of anticancer agents. Eur. J. Med. Chem., 1 Dec 2009, 44 (12), 4862–4888. 1.2 MB. https://doi.org/10.1016/j.ejmech.2009.07.027 #4a MS,NMR,IR

Błachut, D; Wojtasiewicz, K; Krawczyk, K; Maurin, J; Szawkało, J; Czarnocki, Z. Identification and synthesis of by-products found in 4-methylthioamphetamine (4-MTA) produced by the Leuckart method. Forensic Sci. Int., 10 Mar 2012, 216 (1–3), 108–120. 643 kB. https://doi.org/10.1016/j.forsciint.2011.09.005

Nichols, DE. Legal highs: the dark side of medicinal chemistry. Nature, 6 Jan 2011, 469 (7328), 7. 75 kB. https://doi.org/10.1038/469007a

Nichols, DE. The costs of putting knowledge into the wrong hands. Sci. News, 26 Feb 2011, 179 (5), 32. 2.8 MB. https://doi.org/10.1002/scin.5591790529

Fierro, A; Osorio-Olivares, M; Cassels, BK; Edmondson, DE; Sepúlveda-Boza, S; Reyes-Parada, M. Human and rat monoamine oxidase-A are differentially inhibited by (S)-4-alkylthioamphetamine derivatives: Insights from molecular modeling studies. Bioorg. Med. Chem., 1 Aug 2007, 15 (15), 5198–5206. 1.2 MB. https://doi.org/10.1016/j.bmc.2007.05.021 #1 MS,NMR

King, LA. New phenethylamines in Europe. Drug Test. Anal., 1 Jul 2014, 6 (7-8), 808-818. 472 kB. https://doi.org/10.1002/dta.1570

Nichols, DE. Medicinal chemistry and structure-activity relationships. In Amphetamine and its Analogs; Cho, AK; Segal, DS, Eds., Academic Press, San Diego, CA, 1 Jan 1994; pp 3–41. 8.1 MB. #21

Simmler, LD; Liechti, ME. Pharmacology of MDMA- and amphetamine-like new psychoactive substances. In New Psychoactive Substances: Pharmacology, Clinical, Forensic and Analytical Toxicology; Maurer, HH; Brandt, SD, Eds., Springer, Berlin, Heidelberg, 1 Jan 2018; pp 143-164. 298 kB. https://doi.org/10.1007/164_2018_113

Hurtado-Guzmán, C; Fierro, A; Iturriaga-Vásquez, P; Sepúlveda-Boza, S; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of optical isomers and N-substituted derivatives of 4-methylthioamphetamine. J. Enzyme Inhib. Med. Chem., 1 Aug 2003, 18 (4), 339–347. 149 kB. https://doi.org/10.1080/1475636031000118437 #MTA NMR

Gobbi, M; Funicello, M; Gerstbrein, K; Holy, M; Moya, PR; Sotomayor, R; Forray, MI; Gysling, K; Paluzzi, S; Bonanno, G; Reyes-Parada, M; Sitte, HH; Mennini, T. N,N-Dimethyl-thioamphetamine and methyl-thioamphetamine, two non-neurotoxic substrates of 5-HT transporters, have scant in vitro efficacy for the induction of transporter-mediated 5-HT release and currents. J. Neurochem., 1 Jun 2008, 105 (5), 1770–1780. 589 kB. https://doi.org/10.1111/j.1471-4159.2008.05272.x #MTA

Holland, GF; Buck, CJ; Weissman, A. Anorexigenic agents: Aromatic substituted 1-phenyl-2-propylamines. J. Med. Chem., 1 Sep 1963, 6 (5), 519–524. 808 kB. https://doi.org/10.1021/jm00341a011 #4-SCH₃

Walline, CC; Nichols, DE; Carroll, FI; Barker, EL. Comparative molecular field analysis using selectivity fields reveals residues in the third transmembrane helix of the serotonin transporter associated with substrate and antagonist recognition. J. Pharmacol. Exp. Ther., 1 Jun 2008, 325 (3), 791–800. 269 kB. https://doi.org/10.1124/jpet.108.136200 #4-Methylthioamphetamine

Luethi, D; Liechti, ME. Monoamine transporter and receptor interaction profiles in vitro predict reported human doses of novel psychoactive stimulants and psychedelics. Int. J. Neuropsychoph., 1 Oct 2018, 21 (10), 926–931. 254 kB. https://doi.org/10.1093/ijnp/pyy047 #S1 Phenethylamines 4-MTA

Bork, W; Dahlenburg, R; Gimbel, M; Jacobsen-Bauer, A; Zörntlein, S. Herleitung Von Grenzwerten Der „nicht Geringen Menge“ Im Sinne Des Btmg. Toxichem Krimtech, 1 Jan 2019, 86 (1), 5–91. 4.4 MB. #PP-032

Hägele, JS; Basrak, M; Schmid, MG. Enantioselective separation of novel psychoactive substances using a Lux® AMP 3 μm column and HPLC-UV. J. Pharm. Biomed. Anal., 5 Feb 2020, 179, 112967. 3.6 MB. https://doi.org/10.1016/j.jpba.2019.112967 #A6 LC

Clancy, L; Philp, M; Shimmon, R; Fu, S. Development and validation of a color spot test method for the presumptive detection of 25-NBOMe compounds. Drug Test. Anal., 19 Aug 2020, 13 (5), 929-943. 11.3 MB. https://doi.org/10.1002/dta.2905 #4-methylthioamphetamine

Borenstein, S. Scientist haunted by misuse of drugs he invented. JCLIC, 1 Jan 2011, 21 (1), 3-4. 368 kB. #MTA

Nichols, DE; Marona-Lewicka, D; Huang, X; Johnson, MP. Novel serotonergic agents. Drug Des. Discovery, 1 Feb 1993, 9 (3–4), 299–312. 4.7 MB. #MTA

Cozzi, NV. Pharmacological studies of some psychoactive phenylalkylamines: entactogens, hallucinogens, and anorectics. Ph. D. Thesis, University Of Wisconsin-Madison, 1 Jan 1994. 10.6 MB. #MTA LC,MS,NMR

2-MTA · 2-Methylthioamphetamine

3-MTA · 3-Methylthioamphetamine

Thioephedrine · β-Mercaptomethamphetamine · β-SH-MA

4-MeS-BA