Explore 2C-T-2 | PiHKAL

PiHKAL book II entry 2C-T-2

ChemSpider 16787961
PubChem 12074193
Wikidata Q2443432
Erowid 2C-T-2
Erowid Sulfurous Samadhi An Investigation of 2C-T-2 & 2C-T-7
Wikipedia 2C-T-2
Wikipedia, see also 2C (psychedelics)
Blotter 2C-T-2
PsychonautWiki 2C-T-2
swgdrug.org 2,5-Dimethoxy-4-ethylthiophenylamine (2C-T-2)
bluelight.org The Big & Dandy 2C-T-2 Thread
bluelight.org 2C-T-2 Scraps
bluelight.org 2C-T-2 Effects and Ratings Survey Results

Shulgin Index #26 2C-T-2 · Table 5Page 345Row 17

PiHKAL #4 ALEPH-2 · #35 2C-O-4 · #39 2C-T · #41 2C-T-4 · #43 2C-T-7 · #44 2C-T-8 · #45 2C-T-9 · #46 2C-T-13 · #47 2C-T-15 · #48 2C-T-17 · #49 2C-T-21 · #81 FLEA · #87 HOT-2 · #118 MDPR

Phenethylamine: Von der Strucktur zur Funktion 2C-T-2: 8.0 (13) 641, 642 · 8.4 741 · 8.5 (125) 787, 788, 789, 790, 793, 810, 814, 832 · 8.5 808, 822

Stolaroff, MJ; Wells, CW. Preliminary results with new psychoactive agents 2C-T-2 and 2C-T-7. In Yearbook for Ethnomedicine and the Study of Consciousness (Jahrbuch für Ethnomedizin und Bewußtseinsforschung); Rätsch, C; Baker, J, Eds., 1 Jan 1993; Vol. 2, pp 99–117. 185 kB.

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB. #2CT2; 2C-T-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

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

Meyers-Riggs, B. Shulgin’s sulfur symphony—part II. countyourculture, countyourculture: rational exploration of the underground, 3 Apr 2011.

Meyers-Riggs, B. 2C-T-X substitution size and potency. countyourculture, countyourculture: rational exploration of the underground, 1 Apr 2011.

Meyers-Riggs, B. Shulgin’s sulfur symphony—part I. countyourculture, countyourculture: rational exploration of the underground, 15 Jan 2011.

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

Theobald, DS. The 2C-series—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 18 Dec 2006. 1.4 MB.

de Boer, D; Bosman, I. A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs. Pharm. World Sci., 1 Apr 2004, 26 (2), 110–113. 61 kB. https://doi.org/10.1023/B:PHAR.0000018600.03664.36

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

EMCDDA. Report on the risk assessment of 2C-I, 2C-T-2 and 2C-T-7, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, . 1.2 MB. #2C-T-2

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Analysis of phenethylamines and tryptamines in designer drugs using gas chromatography-mass spectrometry. J. Health Sci., 1 Jan 2008, 54 (1), 89–96. 1.9 MB. https://doi.org/10.1248/jhs.54.89

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. https://doi.org/10.1016/j.forsciint.2011.11.003

McGrane, O; Simmons, J; Jacobsen, E; Skinner, C. Alarming trends in a novel class of designer drugs. J. Clinic. Toxicol., 1 Nov 2011, 1 (2), 1000108. 775 kB. https://doi.org/10.4172/2161-0495.1000108

Stolaroff, MJ. Letters to the Editor [re: 2C-T-2, 2C-T-7]. J. Psychoactive Drugs, 1 Jul 1990, 22 (3), 379. 2.0 MB. https://doi.org/10.1080/02791072.1990.10472568

Katagi, M; Tsuchihashi, H. Update on clandestine amphetamines and their analogues recently seen in Japan. J. Health Sci., 1 Jan 2002, 48 (1), 14–21. 181 kB. https://doi.org/10.1248/jhs.48.14 MS

Meyer, MR; Robert, A; Maurer, HH. Toxicokinetics of novel psychoactive substances: Characterization of N-acetyltransferase (NAT) isoenzymes involved in the phase II metabolism of 2C designer drugs. Toxicol. Lett., 5 Jun 2014, 227 (2), 124–128. 865 kB. https://doi.org/10.1016/j.toxlet.2014.03.010

Leth-Petersen, S; Bundgaard, C; Hansen, M; Carnerup, MA; Kehler, J; Kristensen, JL. Correlating the metabolic stability of psychedelic 5-HT_2A agonists with anecdotal reports of human oral bioavailability. Neurochem. Res., 12 Feb 2014, 39 (10), 2018-2023. 625 kB. https://doi.org/10.1007/s11064-014-1253-y

Chapman, SJ; Avanes, AA. PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra. BLOTTER, 1 Aug 2015, 1 (1). 2.6 MB. https://doi.org/10.16889/isomerdesign-1

Chapman, SJ; Avanes, AA. PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra. Supplementary Data. BLOTTER, 1 Aug 2015, 1 (1). 11.9 MB. https://doi.org/10.16889/isomerdesign-1-supp

Maruyama, Y; Matsumoto, Y; Noguchi, H; Yamazaki, M; Inde, S. Analysis of 2C-B and related compounds of 2C-B. JCCL, 1 Jan 2000, (39), 41–57. 476 kB. #2C-T-2 Japanese, English abstract GC,LC,MS,NMR,IR,UV

Matsumoto, Y; Sugiyama, M; Yasuoka, T; Muroi, H; Okazaki, R; Terauchi, Y; Sasatani, T. Qualitative analysis of 2C-B designer drugs. JCCL, 1 Jan 2004, (44), 75–85. 648 kB. #2C-T-2 Japanese, English abstract GC,LC,MS,NMR,IR,UV

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

Rickli, A; Luethi, D; Reinisch, J; Buchy, D; Hoener, MC; Liechti, ME. Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs). Neuropharmacology, 1 Dec 2015, 99, 546–553. 625 kB. https://doi.org/10.1016/j.neuropharm.2015.08.034 #2C-T-2

McGonigal, MK; Wilhide, JA; Smith, PB; Elliott, NM; Dorman, FL. Analysis of synthetic phenethylamine street drugs using direct sample analysis coupled to accurate mass time of flight mass spectrometry. Forensic Sci. Int., 1 Jun 2017, 275, 83–89. 2.3 MB. https://doi.org/10.1016/j.forsciint.2017.02.025 #2C-T-2

Theobald, DS; Maurer, HH. Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series). Biochem. Pharmacol., 1 Jan 2007, 73 (2), 287–297. 365 kB. https://doi.org/10.1016/j.bcp.2006.09.022 #2C-T-2

Wagmann, L; Brandt, SD; Stratford, A; Maurer, HH; Meyer, MR. Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases. Drug Test. Anal., 6 Sep 2018, 11 (2), 318-324. 650 kB. https://doi.org/10.1002/dta.2494 #2C-T-2

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

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.

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.

Shulgin, AT; Shulgin, A; Jacob, P. Letters to the Editor [re 2C-T series]. J. Psychoactive Drugs, 1 Jan 1991, 23 (1), 95–96. 575 kB. https://doi.org/10.1080/02791072.1991.10472583

Maurer, HH. Chemistry, pharmacology, and metabolism of emerging drugs of abuse. Ther. Drug Monit., 1 Oct 2010, 32 (5), 544–549. 142 kB. https://doi.org/10.1097/FTD.0b013e3181eea318 #2C-T-2

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 #2C-T-2

Nagashima, M; Seto, T; Takahashi, M; Suzuki, J; Yasuda, I. Spectrum data of the 3rd Governor-designated drugs and the analyses of uncontrolled drugs purchased Apr. 2005 – Mar. 2006. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2006, 57 109–113. 394 kB. #2C-T-2

Seto, T; Takahashi, M; Nagashima, M; Suzuki, J; Yasuda, I. The identifications and the aspects of the commercially available uncontrolled drugs purchased between Apr. 2003 and Mar. 2004. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2005, 56 75–80. 1.2 MB. #2CT-2 MS,NMR,UV

Takahashi, M; Miyake, H; Nagashima, M; Seto, T; Miyatake, N; Suzuki, J; Kamimura, H; Yasuda, I. Analysis and synthesis of psychedelic phenethylamines. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2003, 54 51–55. 276 kB. #2CT-2 LC,UV,TLC

Zamberlan, F; Sanz, C; Vivot, RM; Pallavicini, C; Erowid, F; Erowid, E; Tagliazucchi, E. The varieties of the psychedelic experience: A preliminary study of the association between the reported subjective effects and the binding affinity profiles of substituted phenethylamines and tryptamines. Front. Integr. Neurosci., 8 Nov 2018, 12 (54). 5.0 MB. https://doi.org/10.3389/fnint.2018.00054 #2C-T-2

Passie, T; Brandt, SD. Self-experiments with psychoactive substances: A historical perspective. In New Psychoactive Substances: Pharmacology, Clinical, Forensic and Analytical Toxicology; Maurer, HH; Brandt, SD, Eds., Springer, Berlin, Heidelberg, 1 Jan 2018; pp 69-110. 563 kB. https://doi.org/10.1007/164_2018_177 #2C-T-2

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 #S2 Phenethylamines 2C-T-2

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. #HP-012

Sexton, JD; Nichols, CD; Hendricks, PS. Population survey data informing the therapeutic potential of classic and novel phenethylamine, tryptamine, and lysergamide psychedelics. Front. Psychiatry, 11 Feb 2020, 10 (896). 529 kB. https://doi.org/10.3389/fpsyt.2019.00896 #2C-T-2

Palamar, JJ; Acosta, P. A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines. Hum. Psychopharmacol. Clin. Exp., 1 Jan 2020, 35 (1), e2719. 764 kB. https://doi.org/10.1002/hup.2719 #2C-T2

Pottie, E; Cannaert, A; Stove, CP. In vitro structure–activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor. Arch. Toxicol., 1 Oct 2020, 94 (10), 3449–3460. 919 kB. https://doi.org/10.1007/s00204-020-02836-w #2C-T-2

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 #2C-T-2

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

Asanuma, M; Miyazaki, I; Funada, M. The neurotoxicity of psychoactive phenethylamines “2C series” in cultured monoaminergic neuronal cell lines. Forensic Toxicol., 1 Jul 2020, 38 (2), 394–408. 5.5 MB. https://doi.org/10.1007/s11419-020-00527-w #2C-T-2

Poortman-Van Der Meer, AJ. The synthesis of 2,5-dimethoxy-4-ethylthiophenethylamine (2C-T-2). A case report. JCLIC, 1 Oct 1999, 9 (4), 17-20. 587 kB. MS,IR

Anon. 2,5-Dimethoxy-4-ethylthiophenethylamine (2C-T-2). JCLIC, 1 Jan 1999, 9 (1), 15-16. 589 kB. MS,IR

Araneda, JF; Baumgarte, M; Lange, M; Maier, AFG; Riegel, SD. Identification of seven psychedelic 2,5‐dimethoxyphenylethylamine‐based designer drugs via benchtop ¹H nuclear magnetic resonance spectroscopy. Magn. Reson. Chem., 23 Aug 2021, n/a. 1.2 MB. https://doi.org/10.1002/mrc.5205 #6 NMR

Kikura-Hanajiri, R; Kawamura, M; Uchiyama, N; Ogata, J; Kamakura, H; Saisho, K; Goda, Y. Analytical data of designated substances (shitei-yakubutsu) controlled by the pharmaceutical affairs law in Japan, Part I: GC-MS and LC-MS. Yakugaku Zasshi, 1 Jun 2008, 128 (6), 971–979. 1.4 MB. https://doi.org/10.1248/yakushi.128.971 #2C-T-2 Incorrect structures drawn. Corrected structures in errata page at end. GC,LC,MS,UV

Uchiyama, N; Kawamura, M; Kamakura, H; Kikura-Hanajiri, R; Goda, Y. Analytical data of designated substances (shitei-yakubutsu) controlled by the pharmaceutical affairs law in Japan, Part II: Color test and TLC. Yakugaku Zasshi, 1 Jan 2008, 128 (6), 981–987. 406 kB. https://doi.org/10.1248/yakushi.128.981 #2C-T-2 TLC

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 #2C-T-2

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 #62

2,5-Dimethoxy-4-methylthioamphetamine · ALEPH · ALEPH-1 · DOT · PARA-DOT

m-DOT · META-DOT

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

3-TE

4-TE · TE

3-TME

4-TME

5-TME

5-TOMSO · TOMSO

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

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

ψ-ALEPH

DOHSM

α-Methyl-4-TM

3-T-TMA

p4-474: 2C-T-2
p4-499: 2C-T-2
p4-502: 2C-T-2
p4-509: 2C-T-2