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PiHKAL book II entry ALEPH

ChemSpider 126887
PubChem 143828
Wikidata Q4716172
Wikipedia Aleph (psychedelic)
Blotter ALEPH
bluelight.org The Big & Dandy DOT/Aleph-1 Thread
Rhodium Shulgin & Nichols: First report on Aleph and 2C-T (IV)
Rhodium Shulgin & Nichols: Three new psychotomimetics: para-DOT - MDMA - α,O-DMS (3)
Rhodium Shulgin: Monomethylthio analogues of TMA-2

Shulgin Index #3 ALEPH · Table 5Page 345Row 13

PiHKAL #4 ALEPH-2 · #39 2C-T · #44 2C-T-8 · #45 2C-T-9 · #125 META-DOT · #139 ORTHO-DOT · #167 4T-MMDA-2

TiHKAL #2 DBT · #46 5-MeS-DMT

Phenethylamine: Von der Strucktur zur Funktion ALEPH: 8.5 (168) 795, 796, 822, 823, 836 · 8.5 808

Jacob, P; Anderson, G; Meshul, CK; Shulgin, AT; Castagnoli, N. Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane. J. Med. Chem., 1 Jan 1977, 20 (10), 1235–1239. 717 kB. https://doi.org/10.1021/jm00220a001 #12c NMR

Shulgin, AT; Nichols, DE. Characterization of three new psychotomimetics. In The Psychopharmacology of Hallucinogens; Stillman, RC; Willette, RE, Eds., Pergamon, 1 Jan 1978; pp 74–83. 210 kB. https://doi.org/10.1016/B978-0-08-021938-7.50010-2 #3 A different layout of the same paper

Nichols, DE; Shulgin, AT. Sulfur analogs of psychotomimetic amines. J. Pharm. Sci., 1 Oct 1976, 65 (10), 1554–1556. 383 kB. https://doi.org/10.1002/jps.2600651040 #IV Rhodium. NMR

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 1 Jul 2012, 4 (7-8), 577-590. 1.0 MB. https://doi.org/10.1002/dta.413

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 #14 ALEPH-1

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 15 Aug 1977, 21 (4), 569–576. 320 kB. https://doi.org/10.1016/0024-3205(77)90099-6 #7

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. https://doi.org/10.1021/jm00144a009 other

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 #8a MS,NMR

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. https://doi.org/10.1016/S0968-0896(03)00437-1 #4

Foster, BC; McLeish, J; Wilson, DL; Whitehouse, LW; Zamecnik, J; Lodge, BA. Biotransformation of tri-substituted methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1 Jan 1992, 22 (12), 1383–1394. 765 kB. https://doi.org/10.3109/00498259209056689 #1d MS,NMR

Corrigall, WA; Coen, KM; Saouda, FM; Robertson, JM; Lodge, BA. Discriminative stimulus properties of substituted amphetamine derivatives. Pharmacol. Biochem. Behav., 1 Dec 1992, 43 (4), 1117–1119. 265 kB. https://doi.org/10.1016/0091-3057(92)90490-7 #DMMTA

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. https://doi.org/10.1016/0024-3205(78)90053-X #7

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 #87 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 #11

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 #6

Nichols, DE. Chemistry and structure–activity relationships of psychedelics. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 1-43. 2.6 MB. https://doi.org/10.1007/7854_2017_475 #43

Nichols, DE. Structure-activity relationships of serotonin 5-HT_2A agonists. WIREs Membr. Transp. Signal, 1 Sep 2012, 1 (5), 559-579. 573 kB. https://doi.org/10.1002/wmts.42

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.

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.

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. #22w

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.

Anderson, GM; Castagnoli, N; Kollman, PA. Quantitative structure-activity relationships in the 2,4,5-ring-substituted phenylisopropylamines. 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 199–217. 623 kB. #8

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.

Nichols, DE; Weintraub, HJR; Pfister, WR; Yim, GKW. The use of rigid analogues to probe hallucinogen receptors. 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 70–83. 717 kB.

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 #10dd

EMCDDA. New drugs in Europe, 2017, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 Aug 2017. 672 kB. #37

Chapman, SJ. Novel Psychoactive Spectra: NMR of (mostly) Novel Psychoactive Substances. BLOTTER, 25 Jun 2018, 3 (2). https://doi.org/10.16889/isomerdesign-6 #ALEPH NMR

Monte, AP. Structure-activity relationships of hallucinogens: Design, synthesis, and pharmacological evaluation of a series of conformationally restricted phenethylamines. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Aug 1995. 10.7 MB. #p-DOT MS,NMR

Nichols, DE. Structure-activity relationships of phenethylamine hallucinogens. J. Pharm. Sci., 1 Aug 1981, 70 (8), 839–849. 1.4 MB. https://doi.org/10.1002/jps.2600700802 #XI

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

King, LA. Designer drugs related to amphetamine (1990–1996). JCLIC, 1 Jul 1996, 6 (3), 15-16. 562 kB. #19

Halberstadt, AL; Luethi, D; Hoener, MC; Trachsel, D; Brandt, SD; Liechti, ME. Use of the head-twitch response to investigate the structure–activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines. Psychopharmacology, 7 Dec 2022, n/a. 1.4 MB. https://doi.org/10.1007/s00213-022-06279-2 #ALEPH

Clare, BW. Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters. J. Med. Chem., 1 Feb 1990, 33 (2), 687–702. 2.8 MB. https://doi.org/10.1021/jm00164a036 #62

Gupta, SP; Singh, P; Bindal, MC. QSAR studies on hallucinogens. Chem. Rev., 1 Dec 1983, 83 (6), 633–649. 2.8 MB. https://doi.org/10.1021/cr00058a003 #53

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 #38

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

2,4-Dimethoxy-5-methylthioamphetamine · m-DOT · META-DOT

4,5-Dimethoxy-2-methylthioamphetamine · o-DOT · ORTHO-DOT

3-TE · 3-Thioescaline

4-TE · 4-Thioescaline · TE

3-TME · 3-Thiometaescaline

4-TME · 4-Thiometaescaline

5-TME · 5-Thiometaescaline

5-TOMSO · TOMSO

2-Ethoxy-5-methoxy-4-methylthiophenethylamine · 2CT-2ETO

2CT-5ETO · 5-Ethoxy-2-methoxy-4-methylthiophenethylamine

2,6-Dimethoxy-4-methylthioamphetamine · ψ-ALEPH

4-Mercaptomethyl-2,5-dimethoxyamphetamine · DOHSM

3,5-Dimethoxy-4-methylthioamphetamine · α-Methyl-4-TM

3,4-Dimethoxy-5-methylthioamphetamine · 3-T-TMA

p1-178: ALEPH: Trials
p1-200: Additional detail on PARADOT; additional trials