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PiHKAL book II entry 2C-I

ChemSpider 8442670
PubChem 10267191
Wikidata Q209255
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Wikipedia, see also 2C (psychedelics)
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swgdrug.org 2,5-Dimethoxy-4-iodophenethylamine (2C-I)
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bluelight.org The Big & Dandy 2C-I Thread

Shulgin Index #23 2C-I · Table 5Page 341Row 8

PiHKAL #22 2C-C · #32 2C-H · #39 2C-T · #65 DOEF · #72 E

Phenethylamine: Von der Strucktur zur Funktion 2C-I: 7.3 (13) 493, 494 · 8.5 (179) 797, 798, 810, 814, 819, 834, 836, 837, 838, 841 · 8.5 808, 822

Braun, U; Shulgin, AT; Braun, G; Sargent, T. Synthesis and body distribution of several iodine-131-labeled central nervous system active drugs. J. Med. Chem., 1 Jan 1977, 20 (12), 1543–1546. 1.1 MB. https://doi.org/10.1021/jm00222a001

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB. #2CI (25I); 2C-I

Ettrup, A; Hansen, M; Santini, MA; Paine, J; Gillings, N; Palner, M; Lehel, S; Herth, MM; Madsen, J; Kristensen, JL; Begtrup, M; Knudsen, GM. Radiosynthesis and in vivo evaluation of a series of substituted ¹¹C-phenethylamines as 5-HT_2A agonist PET tracers. Eur. J. Nucl. Med. Mol. Imaging, 1 Apr 2011, 38 (4), 681–693. 752 kB. https://doi.org/10.1007/s00259-010-1686-8

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT_2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. https://doi.org/10.1002/cmdc.200800133 #12

Meyers-Riggs, B. The halogenated 2Cs. countyourculture, countyourculture: rational exploration of the underground, 29 Sep 2010.

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)_2A and 5-HT_2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. https://doi.org/10.1124/jpet.106.117507

Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT_2A and 5-HT_2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. https://doi.org/10.1038/sj.bjp.0704747

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT_2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. https://doi.org/10.1124/mol.107.039255

Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE. Molecular interaction of serotonin 5-HT_2A receptor residues Phe339^(6.51) and Phe340^(6.52) with superpotent N-benzyl phenethylamine agonists. Mol. Pharmacol., 1 Jan 2006, 70 (6), 1956–1964. 361 kB. https://doi.org/10.1124/mol.106.028720

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. https://doi.org/10.1002/jps.2600680733

Johnson, MP; Mathis, CA; Shulgin, AT; Hoffman, AJ; Nichols, DE. [¹²⁵I]-2-(2,5-Dimethoxy-4-iodophenyl)aminoethane ([¹²⁵I]-2C-I) as a label for the 5-HT₂ receptor in rat frontal cortex. Pharmacol. Biochem. Behav., 1 Jan 1990, 35 (1), 211–217. 724 kB. https://doi.org/10.1016/0091-3057(90)90228-A

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

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.

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.

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.

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., , 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). 775 kB. https://doi.org/10.4172/2161-0495.1000108

Villalobos, CA; Bull, P; Sáez, P; Cassels, BK; Huidobro-Toro, JP. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT_2A receptor antagonists in Xenopus laevis oocytes. Br. J. Pharmacol., 1 Apr 2004, 141 (7), 1167–1174. 271 kB. https://doi.org/10.1038/sj.bjp.0705722

Kanai, K; Takekawa, K; Kumamoto, T; Ishikawa, T; Ohmori, T. Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC-MS, and GC-MS. Forensic Toxicol., 1 Nov 2008, 26 (2), 6–12. 406 kB. https://doi.org/10.1007/s11419-008-0041-2

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; Vol. 11, pp 243–333. 2.6 MB. https://doi.org/10.1007/978-1-4757-0510-2_6 Rhodium.

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

Halberstadt, AL. Pharmacology and Toxicology of N-Benzylphenethylamine (“NBOMe”) Hallucinogens. In Current Topics in Behavioral Neurosciences; , ; pp 1–29. 826 kB. https://doi.org/10.1007/7854_2016_64

Halberstadt, AL; Geyer, MA. Effects of the hallucinogen 2,5-dimethoxy-4-iodophenethylamine (2C-I) and superpotent N-benzyl derivatives on the head twitch response. Neuropharmacology, 1 Feb 2014, 77, 200–207. 1.4 MB. https://doi.org/10.1016/j.neuropharm.2013.08.025

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-I 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-I

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-I

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-I

Collins, M. Some new psychoactive substances: Precursor chemical and synthesis-driver end-products. Drug Test. Analysis, 1 Jul 2001, 3 (7–8), 404–416. 178 kB. https://doi.org/10.1002/dta.315

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 #Table 2: H

Halberstadt, AL; Geyer, MA. Effect of hallucinogens on unconditioned behavior. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 159-199. 652 kB. https://doi.org/10.1007/7854_2016_466

Montenarh, D; Hopf, M; Warth, S; Maurer, HH; Schmidt, P; Ewald, AH. A simple extraction and LC-MS/MS approach for the screening and identification of over 100 analytes in eight different matrices: Detection of 130 analytes in eight biosamples using only one LC-MS/MS method. Drug Test. Analysis, 1 Mar 2015, 7 (3), 214-240. 593 kB. https://doi.org/10.1002/dta.1657

Burns, L; Roxburgh, A; Matthews, A; Bruno, R; Lenton, S; Van Buskirk, J. The rise of new psychoactive substance use in Australia. Drug Test. Analysis, 1 Jul 2014, 6 (7-8), 846-849. 422 kB. https://doi.org/10.1002/dta.1626

Vidal Giné, C; Espinosa, IF; Vilamala, MV. New psychoactive substances as adulterants of controlled drugs. A worrying phenomenon? Drug Test. Analysis, 1 Jul 2014, 6 (7-8), 819-824. 113 kB. https://doi.org/10.1002/dta.1610

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

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

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-I

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-I

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

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.

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, ; pp 74–91. 51 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, ; Vol. 55 (3), pp 3–29. 29.7 MB. #10f

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. #42

Arantes, LC; Júnior, EF; Figueiredo de Souza, L; Cardoso, AC; Alcântara, TLF; Lião, LM; Machado, Y; Lordeiro, RA; Neto, JC; Andrade, AFB. 25I-NBOH: A new potent serotonin 5-HT_2A receptor agonist identified in blotter paper seizures in Brazil. Forensic Toxicol., 1 Jul 2017, 35 (2), 408–414. 1.3 MB. https://doi.org/10.1007/s11419-017-0357-x #2C-I GC,MS,NMR,IR

Neto, JC; Andrade, AFB; Lordeiro, RA; Machado, Y; Elie, M; Júnior, EF; Arantes, LC. Preventing misidentification of 25I-NBOH as 2C-I on routine GC–MS analyses. Forensic Toxicol., 1 Jul 2017, 35 (2), 415–420. 1.3 MB. https://doi.org/10.1007/s11419-017-0362-0 #2C-I

Li, Y; Wang, M; Li, A; Zheng, H; Wei, Y. Identification of the impurities in 2,5-dimethoxy-4-ethylphenethylamine tablets by high performance liquid chromatography mass spectrometry-ion trap-time of flight. Anal. Methods, 24 Nov 2016, 8 (46), 8179–8187. 1.1 MB. https://doi.org/10.1039/C6AY02162J #imp 7

Nagai, F; Nonaka, R; Kamimura, KSH. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain. Eur. J. Pharmacol., 22 Mar 2007, 559 (2), 132–137. 399 kB. https://doi.org/10.1016/j.ejphar.2006.11.075 #2C-I

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. #2C-I MS,NMR,UV

Suzuki, J; Seto, T; Nagashima, M; Takahashi, M; Okumoto, C; Yasuda, I. Measurement of purity of Governor-designated drugs and estimated structural formula of the impurities. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2005, 56 69–74. 1.0 MB. #2C-I LC,MS,NMR,IR,UV,TLC,other

Machiko, N; Takako, S; Misako, T; Suzuki, H; Yasuda, I. Analytical methods and spectrum data of 4 Governor-designated drugs. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2005, 56 59–64. 1.9 MB. #2C-I

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. #2C-I

Monte, AP; Marona-Lewicka, D; Parker, MA; Wainscott, DB; Nelson, DL; Nichols, DE. Dihydrobenzofuran analogues of hallucinogens. 3. 1 Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups. J. Med. Chem., 1 Jan 1996, 39 (15), 2953–2961. 290 kB. https://doi.org/10.1021/jm960199j #2b

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. Analysis, 6 Sep 2018, n/a. 650 kB. https://doi.org/10.1002/dta.2494 #2C-I

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 n/a. 5.0 MB. https://doi.org/10.3389/fnint.2018.00054 #2C-I

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-I

McCorvy, JD. Mapping the binding site of the 5-HT_2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics. Ph. D. Thesis, Purdue University, 1 Jan 2012. 3.9 MB. #2C-I

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-009

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. #2C-I MS,NMR

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