Explore 4-Ethylthio-2,5-dimethoxyamphetamine

PiHKAL book II entry ALEPH-2

ChemSpider 8439835
PubChem 10264356
Wikidata Q16527585
Wikipedia Aleph (psychedelic)

Shulgin Index #4 ALEPH-2 · Table 5Page 345Row 19

Phenethylamine: Von der Strucktur zur Funktion ALEPH-2: 8.5 (169) 795, 796, 810, 836 · 8.5 808

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB. #ALEPH2; Aleph-2

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. https://doi.org/10.1371/journal.pone.0009019

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 #13

Reyes-Parada, M; Scorza, C; Romero, V; Silveira, R; Medina, JH; Andrus, D; Nichols, DE; Cassels, BK. (±)-1-(2,5-Dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2), a novel putative anxiolytic agent lacking affinity for benzodiazepine sites and serotonin-1A receptors. N-S. Arch. Pharmacol., 1 Nov 1996, 354 (5), 579–585. 1.4 MB. https://doi.org/10.1007/BF00170831 #ALEPH-2

Acuña-Castillo, C; Scorza, C; Reyes-Parada, M; Cassels, BK; Huidobro-Toro, JP. ALEPH-2, a suspected anxiolytic and putative hallucinogenic phenylisopropylamine derivative, is a 5-HT_2A and 5-HT_2C receptor agonist. Life Sci., 17 Nov 2000, 67 (26), 3241–3247. 89 kB. https://doi.org/10.1016/S0024-3205(00)00906-1

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 #7 NMR,IR

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. https://doi.org/10.1021/jm0493109 #8b MS,NMR

Parrish, JC. Toward a molecular understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2006. 5.5 MB.

Parrish, JC; Braden, MR; Gundy, E; Nichols, DE. Differential phospholipase C activation by phenylalkylamine serotonin 5-HT_2A receptor agonists. J. Neurochem., 1 Dec 2005, 95 (6), 1575–1584. 301 kB. https://doi.org/10.1111/j.1471-4159.2005.03477.x

Scorza, MC; Reyes-Parada, M; Silveira, R; Viola, H; Medina, JH; Viana, MB; Zangrossi, H; Graeff, FG. Behavioral effects of the putative anxiolytic (±)-1-(2,5-dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2) in rats and mice. Pharmacol. Biochem. Behav., 1 May 1996, 54 (2), 355–361. 504 kB. https://doi.org/10.1016/0091-3057(95)02149-3

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; pp 243–333. 2.6 MB. https://doi.org/10.1007/978-1-4757-0510-2_6 #88 Rhodium.

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. https://doi.org/10.1016/j.bmc.2003.10.027 #3

Ogino, M; Naiki, T; Orui, H; Kosone, K; Yamazaki, M. Study of method for identifying phenethylamine drugs. JCCL, 11 Feb 2011, 50, 63-82. 627 kB. Japanese, English abstract LC,MS,NMR,IR

Zhang, S; Fan, Y; Shi, Z; Cheng, S. DFT-based QSAR and action mechanism of phenylalkylamine and tryptamine hallucinogens. Chin. J. Chem., 1 Apr 2011, 29 (4), 623–630. 166 kB. https://doi.org/10.1002/cjoc.201190132 #4

Shulgin, AT. Basic Pharmacology and Effects. In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 24 Apr 2003; pp 67–137. 6.3 MB.

Shulgin, AT. Hallucinogens. In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., John Wiley & Sons, Inc., 1 Jan 1981; pp 1109–1137. 4.7 MB. #22x

Jacob, P; Shulgin, AT. Structure-activity relationships of the classic hallucinogens and their analogs. In Hallucinogens: An update. NIDA Research Monograph 146; Lin, GC; Glennon, RA, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1994; pp 74–91. 51 kB.

Braun, U; Braun, G; Jacob, P; Nichols, DE; Shulgin, AT. Mescaline Analogs: Substitutions at the 4-Position. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 27–37. 497 kB. Rhodium.

Shulgin, AT. Chemistry of psychotomimetics. In Handbook of Experimental Pharmacology. Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs; Hoffmeister, F; Stille, G, Eds., Springer-Verlag, Berlin, 1 Jan 1982; Vol. 55 (3), pp 3–29. 928 kB. https://doi.org/10.1007/978-3-642-67770-0_1 #10ee

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Creation and application of psychoactive designer drugs data library using liquid chromatography with photodiode array spectrophotometry detector and gas chromatography–mass spectrometry. Talanta, 15 Feb 2009, 77 (4), 1245–1272. 1.2 MB. https://doi.org/10.1016/j.talanta.2008.07.062 #ALEPH-2 GC,LC,MS,UV

Fenderson5555. Thioethers from PIHKAL, 2-C-T and ALEPH series. , 4 Jun 2020. . Fenderson5555 21.3 MB. #ALEPH-2

Nahoko, U; Norimasa, M; Maiko, K; Ruri, K; Yukihiro, G. Analysis of newly distributed designer drugs detected in the products purchased in fiscal year 2008. Yakugaku Zasshi, 1 Feb 2010, 130 (2), 263–270. 826 kB. https://doi.org/10.1248/yakushi.130.263 #ALEPH-2 GC,LC,MS,NMR,UV

Nagashima, M; Seto, T; Suzuki, J. Analyses of uncontrolled drugs purchased from April 2007 to March 2008 and newly found compounds. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2008, 59 71–77. 743 kB. #ALEPH-2 LC,NMR,UV

Clare, BW. The frontier orbital phase angles: Novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens. J. Med. Chem., 24 Sep 1998, 41 (20), 3845–3856. 239 kB. https://doi.org/10.1021/jm980144c #51

2C-T-4 · 4-Isopropylthio-2,5-dimethoxyphenethylamine

4-Isopropylthio-2,6-dimethoxyphenethylamine · ψ-2C-T-4

2C-T-7 · 4-Propylthio-2,5-dimethoxyphenethylamine

3-TASB · 3-Thioasymbescaline

4-TASB · 4-Thioasymbescaline

5-TASB · 5-Thioasymbescaline

TP · Thioproscaline

3-TSB · 3-Thiosymbescaline

4-TSB · 4-Thiosymbescaline

2-Ethoxy-4-ethylthio-5-methoxyphenethylamine · 2CT2-2ETO

2CT2-5ETO · 5-Ethoxy-4-ethylthio-2-methoxyphenethylamine

4C-T · α-Ethyl-2,5-dimethoxy-4-methylthiophenethylamine

2,4,3-2C-T-7 · 3-Propylthio-2,4-dimethoxyphenethylamine

2-Propylthio-3,4-dimethoxyphenethylamine · 3,4,2-2C-T-7

2,3,4-2C-T-7 · 4-Propylthio-2,3-dimethoxyphenethylamine

2,5,3-2C-T-7 · 3-Propylthio-2,5-dimethoxyphenethylamine

3,5,2-2C-T-7 · 3,5-Dimethoxxy-2-propylthiophenethylamine

2,3,5-2C-T-7 · 2,3-Dimethoxxy-5-propylthiophenethylamine

4,5,2-2C-T-7 · 4,5-Dimethoxy-2-propylthiophenethylamine

4-Methylthio-2,5-dimethoxymethamphetamine · N-Me-ALEPH

3,4,5-2C-T-7 · 3,4-Dimethoxy-5-propylthiophenethylamine

2,6,3-2C-T-7 · 2,6-Dimethoxy-3-propylthiophenethylamine

3,6,2-2C-T-7 · 3,6-Dimethoxy-2-propylthiophenethylamine

2,3,6-2C-T-7 · 2,3-Dimethoxy-6-propylthiophenethylamine

2,4-Dimethoxy-6-propylthiophenethylamine · 4,6,2-2C-T-7

4-Ethylthio-2,6-dimethoxyamphetamine · ψ-ALEPH-2

2,6-Dimethoxy-4-propylthioamphetamine · ψ-2C-T-7

4-Methylthiomethyl-2,5-dimethoxyamphetamine · DOMSM · DOMeSM

3-TIP · 4-Isopropoxy-3-methoxy-5-methylthiophenethylamine

p1-194: 5-MeO-DMT; ALEPH-2: Trials
p2-205: ALEPH-2
p2-220: ALEPH-2
p2-318: ALEPH-2