Explore 2C-C | PiHKAL

PiHKAL book II entry 2C-C

ChemSpider 21106221
PubChem 29979100
Wikidata Q114905
Erowid 2C-C
Wikipedia 2C-C
Wikipedia, see also 2C (psychedelics)
Blotter 2C-C
PsychonautWiki 2C-C
Project Response 2C-C (1109-14A)
swgdrug.org 2,5-Dimethoxy-4-chlorophenethylamine (2C-C)
bluelight.org The Big & Dandy 2C-C Thread Part 2
bluelight.org The Big & Dandy 2C-C Thread Part 1
Rhodium 2C-C and DOC with N-chlorosuccinimide and perchloric acid
Rhodium Synthesis of 4-chloro-2,5-dimethoxyphenethylamine (2C-C)
bluelight.org 2C-C Effects and Ratings Survey Results
aipsin.com 2C-C (Iss. 6, Jun 2020: X-71)

Shulgin Index #19 2C-C · Table 5Page 340Row 19

PiHKAL #32 2C-H · #39 2C-T · #64 DOC

Phenethylamine: Von der Strucktur zur Funktion 2C-C: 8.5 (178) 797 · 8.5 808 · 10.3 (24) 939

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. #2C-C LC,MS,NMR

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15), 7415-7423. 366 kB. https://doi.org/10.1016/j.bmc.2008.06.009

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

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

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-C Japanese, English abstract GC,LC,MS,NMR,IR,UV

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-C

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-C

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 #35

Vidal Giné, C; Espinosa, IF; Vilamala, MV. New psychoactive substances as adulterants of controlled drugs. A worrying phenomenon? Drug Test. Anal., 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. 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.

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 #2CC

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-C

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-C

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-C MS,NMR,UV

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-C

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-C

Ando, T; Sugiyama, M; Osaki, N; Watase, J. Analysis of phenethylamine analogues. JCCL, 1 Aug 2011, (51), 51–58. 474 kB. #2C-C Japanese, English abstract LC,MS,NMR,IR

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-007

Cheng, AC; Castagnoli, N. Synthesis and physicochemical and neurotoxicity studies of 1-(4-substituted-2,5-dihydroxyphenyl)-2-aminoethane analogs of 6-hydroxydopamine. J. Med. Chem., 1 Apr 1984, 27 (4), 513–520. 1.2 MB. https://doi.org/10.1021/jm00370a014 #14c NMR

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-C

Poulie, CBM; Jensen, AA; Halberstadt, AL; Kristensen, JL. DARK Classics in Chemical Neuroscience: NBOMes. ACS Chem. Neurosci., 2 Dec 2020, 11 (23), 3860-3869. 860 kB. https://doi.org/10.1021/acschemneuro.9b00528 #2C-C

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

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-C

Elbardisy, HM; Foster, CW; Marron, J; Mewis, RE; Sutcliffe, OB; Belal, TS; Talaat, W; Daabees, HG; Banks, CE. Quick test for determination of N-bombs (Phenethylamine derivatives, NBOMe) using high-performance liquid chromatography: A comparison between photodiode array and amperometric detection. ACS Omega, 10 Sep 2019, 4 (11), 14439–14450. 3.4 MB. https://doi.org/10.1021/acsomega.9b01366 #1b LC

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-C

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-C

Block, R. 2C-B analog encountered in Wisconsin. JCLIC, 1 Oct 1994, 4 (4), 12-15. 553 kB. GC,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 #2 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-C 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-C TLC

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 #53

BO3M2C

2-Cl-3,4-DMPEA

2-Cl-4,5-DMPEA

3-Cl-4,5-DMPEA

ψ-2C-C

p4-462: α-CP-2C-D; 2C-C; 4-HO-DET; 4-HO-DPT; 4-MeO-DET; 5,6-MDO-MIPT; BOAD; BOD; DMA; DOIB; DPT; ORTHO-MDA