Menu
Home
People
Places
Arts
History
Plants & Animals
Science
Life & Culture
Technology
Reference.org
2C-C
open-in-new
<h2 id="effects">Effects</h2> <p>Over the approximate dose range 20–40 mg, visual effects last approximately 4 to 8 hours.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> </p> <h2 id="pharmacology">Pharmacology</h2> 2C-C activities<table><tbody><tr><th><a href="/facts/Biological_target/7bakbMFR">Target</a></th><th><a href="/facts/Affinity_(pharmacology)/44QLL4eU">Affinity</a> (Ki, nM)</th></tr><tr><td><a href="/facts/5-HT1A_receptor/aMCB3tvc">5-HT1A</a></td><td>190–740 (Ki)>10,000 (<a href="/facts/Half-maximal_effective_concentration/x7oD7ITx">EC50</a>Tooltip half-maximal effective concentration)<25% (<a href="/facts/Maximal_efficacy/wRugal9r">Emax</a>Tooltip maximal efficacy)</td></tr><tr><td><a href="/facts/5-HT1B_receptor/zM2xads8">5-HT1B</a>–<a href="/facts/5-HT1F_receptor/7rRWhUwl">5-HT1F</a></td><td>ND</td></tr><tr><td><a href="/facts/5-HT2A_receptor/YfTglQKQ">5-HT2A</a></td><td>5.47–13 (Ki)9.27–200 (EC50)49–102% (Emax)</td></tr><tr><td><a href="/facts/5-HT2B_receptor/Sy104fUR">5-HT2B</a></td><td>ND (Ki)280 (EC50)81% (Emax)</td></tr><tr><td><a href="/facts/5-HT2C_receptor/RuyLstWf">5-HT2C</a></td><td>5.4–90 (Ki)24.2 (EC50)94% (Emax)</td></tr><tr><td><a href="/facts/5-HT3_receptor/7Qa2T8v3">5-HT3</a>–<a href="/facts/5-HT7_receptor/rcpLc6FL">5-HT7</a></td><td>ND</td></tr><tr><td><a href="/facts/Alpha-1A_adrenergic_receptor/R6Qr1DF5">α1A</a></td><td>13,000</td></tr><tr><td><a href="/facts/Alpha-1B_adrenergic_receptor/841rFlgm">α1B</a>, <a href="/facts/Alpha-1D_adrenergic_receptor/9RDfgC1E">α1D</a></td><td>ND</td></tr><tr><td><a href="/facts/Alpha-2A_adrenergic_receptor/csNJEymK">α2A</a></td><td>530</td></tr><tr><td><a href="/facts/Alpha-2B_adrenergic_receptor/4NgonAtn">α2B</a>, <a href="/facts/Alpha-2C_adrenergic_receptor/z8rNNBGW">α2C</a></td><td>ND</td></tr><tr><td><a href="/facts/Beta-1_adrenergic_receptor/mKQVE8tB">β1</a>–<a href="/facts/Beta-3_adrenergic_receptor/SaAcXPMG">β3</a></td><td>ND</td></tr><tr><td><a href="/facts/D1_receptor/fkWRTblS">D1</a></td><td>13,000</td></tr><tr><td><a href="/facts/D2_receptor/SmmP3QyU">D2</a></td><td>2,100</td></tr><tr><td><a href="/facts/D3_receptor/e1L1KnJq">D3</a></td><td>17,000</td></tr><tr><td><a href="/facts/D4_receptor/26otIqul">D4</a></td><td>ND</td></tr><tr><td><a href="/facts/D5_receptor/VAAvdkLS">D5</a></td><td>ND</td></tr><tr><td><a href="/facts/H1_receptor/L6DzvF7A">H1</a></td><td>14,000</td></tr><tr><td><a href="/facts/H2_receptor/VshlTrU4">H2</a>–<a href="/facts/H4_receptor/bKzpWKnD">H4</a></td><td>ND</td></tr><tr><td><a href="/facts/Muscarinic_acetylcholine_M1_receptor/ne0YBBqI">M1</a>–<a href="/facts/Muscarinic_acetylcholine_M5_receptor/8UR0qo0w">M5</a></td><td>ND</td></tr><tr><td><a href="/facts/I1_receptor/YfluMaRh">I1</a></td><td>ND</td></tr><tr><td><a href="/facts/Sigma-1_receptor/qje6l9GW">σ1</a>, <a href="/facts/Sigma-2_receptor/yISCj0hs">σ2</a></td><td>ND</td></tr><tr><td><a href="/facts/Trace_amine-associated_receptor_1/Xf3Qpjtw">TAAR1</a>Tooltip Trace amine-associated receptor 1</td><td>4,100 (Ki) (mouse)110 (Ki) (rat)2,300 (EC50) (mouse)340 (EC50) (rat)>10,000 (EC50) (human)57% (Emax) (mouse)51% (Emax) (rat)</td></tr><tr><td><a href="/facts/Serotonin_transporter/VPh5wtCy">SERT</a>Tooltip Serotonin transporter</td><td>24,000 (Ki)72,000–74,000 (<a href="/facts/Half-maximal_inhibitory_concentration/zdz6qVBP">IC50</a>Tooltip half-maximal inhibitory concentration)>100,000 (EC50) (rat)</td></tr><tr><td><a href="/facts/Norepinephrine_transporter/532N8LIg">NET</a>Tooltip Norepinephrine transporter</td><td>>30,000 (Ki)63,000–93,000 (IC50)100,000 (EC50) (rat)</td></tr><tr><td><a href="/facts/Dopamine_transporter/V9I2Uy1p">DAT</a>Tooltip Dopamine transporter</td><td>>30,000 (Ki)305,000 (IC50)>100,000 (EC50) (rat)</td></tr><tr><td><a href="/facts/Monoamine_oxidase_A/VXqw1LUU">MAO-A</a>Tooltip Monoamine oxidase A</td><td>ND (IC50)</td></tr><tr><td><a href="/facts/Monoamine_oxidase_B/wa0xq7KL">MAO-B</a>Tooltip Monoamine oxidase B</td><td>ND (IC50)</td></tr><tr><td colspan="2">Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: <a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a><a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a><a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a><a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a><a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a><a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a><a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a></td></tr></tbody></table> <p>2C-C acts as an <a href="/facts/Agonist/nz8U5NNp">agonist</a> of the <a href="/facts/Serotonin/EzY58q4a">serotonin</a> <a href="/facts/5-HT2_receptor/83TWw6EC">5-HT2 receptors</a>.<a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a><a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a> It also binds to the serotonin <a href="/facts/5-HT1A_receptor/aMCB3tvc">5-HT1A receptor</a> with 15-fold lower <a href="/facts/Affinity_(pharmacology)/44QLL4eU">affinity</a> than for the serotonin <a href="/facts/5-HT2A_receptor/YfTglQKQ">5-HT2A receptor</a>.<a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a><a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a> The drug shows little or no affinity for the <a href="/facts/Monoamine_transporter/UpsxmjhK">monoamine transporters</a> (MATs) and shows very weak or negligible <a href="/facts/Monoamine_reuptake_inhibition/NKWd6IvY">monoamine reuptake inhibition</a>.<a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a><a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a> It shows high affinity for the rat <a href="/facts/Trace_amine-associated_receptor_1/Xf3Qpjtw">trace amine-associated receptor 1</a> (TAAR1), but only weak affinity for the mouse TAAR1.<a class="footnote-ref" id="fnref:17" href="#fn:17"><sup>17</sup></a><a class="footnote-ref" id="fnref:18" href="#fn:18"><sup>18</sup></a> </p><p>In contrast to many other psychedelics, 2C-C, as well as <a href="/facts/2C-P/oSMUJNKw">2C-P</a> and certain 2C <a href="/facts/NBOMe/dgahclhS">NBOMe</a> <a href="/facts/Structural_analog/3aysWSVG">analogues</a>, has shown <a href="/facts/Positive_reinforcement/bn271VLa">reinforcing</a> effects in rodents.<a class="footnote-ref" id="fnref:19" href="#fn:19"><sup>19</sup></a><a class="footnote-ref" id="fnref:20" href="#fn:20"><sup>20</sup></a> It produces <a href="/facts/Dose-dependent/DLcuLdHc">dose-dependent</a> <a href="/facts/Conditioned_place_preference/C69ShbqG">conditioned place preference</a> (CPP) in mice and <a href="/facts/Self-administration/QpVQv4xS">self-administration</a> in rats.<a class="footnote-ref" id="fnref:21" href="#fn:21"><sup>21</sup></a><a class="footnote-ref" id="fnref:22" href="#fn:22"><sup>22</sup></a> These findings suggest that 2C-C may have <a href="/facts/Misuse_potential/e3jLXFsF">misuse potential</a>.<a class="footnote-ref" id="fnref:23" href="#fn:23"><sup>23</sup></a><a class="footnote-ref" id="fnref:24" href="#fn:24"><sup>24</sup></a> The <a href="/facts/Mechanism_of_action/Sjk8vfV4">mechanism</a> by which these effects are produced is unknown.<a class="footnote-ref" id="fnref:25" href="#fn:25"><sup>25</sup></a> However, 2C-C was found to decrease <a href="/facts/Dopamine_transporter/V9I2Uy1p">dopamine transporter</a> (DAT) <a href="/facts/Gene_expression/alCPohLR">expression</a> and to increase DAT <a href="/facts/Phosphorylation/LXUEEeIL">phosphorylation</a> in the <a href="/facts/Nucleus_accumbens/2M43u5X4">nucleus accumbens</a> and <a href="/facts/Medial_prefrontal_cortex/dypYIrwx">medial prefrontal cortex</a> (mPFC) similarly to <a href="/facts/Methamphetamine/vS1jloMe">methamphetamine</a> in rodents.<a class="footnote-ref" id="fnref:26" href="#fn:26"><sup>26</sup></a><a class="footnote-ref" id="fnref:27" href="#fn:27"><sup>27</sup></a> Decreased DAT expression may result in reduced <a href="/facts/Dopamine/5gNy8Xkd">dopamine</a> <a href="/facts/Reuptake/eUjJ6YyY">reuptake</a>, while DAT phosphorylation is associated with dopamine <a href="/facts/Reverse_transport/CmtwvfGz">reverse transport</a> and <a href="/facts/Efflux_pump/EoYrVuxV">efflux</a>, in turn increasing <a href="/facts/Extracellular/UEPUhSN8">extracellular</a> dopamine levels.<a class="footnote-ref" id="fnref:28" href="#fn:28"><sup>28</sup></a><a class="footnote-ref" id="fnref:29" href="#fn:29"><sup>29</sup></a> </p><p>2C-C has also been found to produce <a href="/facts/Neurotoxicity/FrgTICfX">neurotoxicity</a> at high doses in rodents, which appears to be mediated via <a href="/facts/Neuroinflammation/4D4PjYz2">neuroinflammation</a>.<a class="footnote-ref" id="fnref:30" href="#fn:30"><sup>30</sup></a> </p> <h2 id="interactions">Interactions</h2> <p class="note">See also: <a href="/facts/Psychedelic_drug/aj9GNANW">Psychedelic drug § Interactions</a>, and <a href="/facts/Trip_killer/XcoBCslc">Trip killer § Serotonergic psychedelic antidotes</a></p> <p>2C drugs like 2C-C are known to be <a href="/facts/Drug_metabolism/I5nQ28Ma">metabolized</a> by the <a href="/facts/Monoamine_oxidase/4bJuxUFy">monoamine oxidase</a> (MAO) <a href="/facts/Enzyme/DSI1Fh7y">enzymes</a> <a href="/facts/MAO-A/VXqw1LUU">MAO-A</a> and <a href="/facts/MAO-B/wa0xq7KL">MAO-B</a>.<a class="footnote-ref" id="fnref:31" href="#fn:31"><sup>31</sup></a><a class="footnote-ref" id="fnref:32" href="#fn:32"><sup>32</sup></a> <a href="/facts/Monoamine_oxidase_inhibitor/obewT56a">Monoamine oxidase inhibitors</a> (MAOIs) such as <a href="/facts/Phenelzine/lwCH0IDJ">phenelzine</a>, <a href="/facts/Tranylcypromine/YVIArwgA">tranylcypromine</a>, <a href="/facts/Moclobemide/vtr3h3D9">moclobemide</a>, and <a href="/facts/Selegiline/2K3IEPMT">selegiline</a> may potentiate the effects of 2C drugs like 2C-C.<a class="footnote-ref" id="fnref:33" href="#fn:33"><sup>33</sup></a><a class="footnote-ref" id="fnref:34" href="#fn:34"><sup>34</sup></a><a class="footnote-ref" id="fnref:35" href="#fn:35"><sup>35</sup></a> This may result in <a href="/facts/Overdose/Jlo2AX3Y">overdose</a> and serious <a href="/facts/Toxicity/qa96rs60">toxicity</a>.<a class="footnote-ref" id="fnref:36" href="#fn:36"><sup>36</sup></a><a class="footnote-ref" id="fnref:37" href="#fn:37"><sup>37</sup></a> </p> <h2 id="legal-status">Legal status</h2> <h3>China</h3> <p>As of October 2015 2C-C is a controlled substance in China.<a class="footnote-ref" id="fnref:38" href="#fn:38"><sup>38</sup></a> </p> <h3>Canada</h3> <p>As of October 31, 2016; 2C-C is a controlled substance (Schedule III) in Canada.<a class="footnote-ref" id="fnref:39" href="#fn:39"><sup>39</sup></a> </p> <h3>Germany</h3> <p>2C-C is an <a href="/facts/Drugs_controlled_by_the_German_Bet%C3%A4ubungsmittelgesetz/CjtAL6X3">Anlage I</a> controlled drug. </p> <h3>Sweden</h3> <p><a href="/facts/Riksdag/uarwUozH"><i>Sveriges riksdags</i></a> health ministry Statens folkhälsoinstitut classified 2C-C as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated <i>Act on the Prohibition of Certain Goods Dangerous to Health</i>) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as 2,5-dimetoxi-4-klorfenetylamin (2C-C), making it illegal to sell or possess.<a class="footnote-ref" id="fnref:40" href="#fn:40"><sup>40</sup></a> </p> <h3>United States</h3> <p>As of July 9, 2012, in the <a href="/facts/United_States/P0sCdLe5">United States</a> 2C-C is a <a href="/facts/Controlled_Substances_Act/8laeNsgD">Schedule I</a> substance under the <a href="/facts/Food_and_Drug_Administration_Safety_and_Innovation_Act_of_2012/M9MUzkva">Food and Drug Administration Safety and Innovation Act of 2012</a>, making possession, distribution and manufacture illegal.<a class="footnote-ref" id="fnref:41" href="#fn:41"><sup>41</sup></a> </p> <h2 id="analogues-and-derivatives">Analogues and derivatives</h2> <p>Analogues and derivatives of 2C-C: </p><p>25C-NB*: </p> <ul><li><a href="/facts/25C-NBF/777vLXCG">25C-NBF</a></li> <li>25C-NBMD</li> <li><a href="/facts/25C-NBOH/XoIhaERk">25C-NBOH</a></li> <li><a href="/facts/25C-NBOMe/gJVqjJkG">25C-NBOMe</a> (NBOMe-2CC)</li> <li><a href="/facts/25C-NB3OMe/qAEPau1F">25C-NB3OMe</a></li> <li><a href="/facts/25C-NB4OMe/a14kjrLH">25C-NB4OMe</a></li></ul> <p><a href="/facts/N-(2C)-fentanyl/pJrN2yB2">N-(2C)-fentanyl</a>: </p> <ul><li>N-(2C-C)-fentanyl<a class="footnote-ref" id="fnref:42" href="#fn:42"><sup>42</sup></a></li></ul> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Phenethylamine/XyjysSul">Phenethylamines</a></li> <li><a href="/facts/2,5-Dimethoxy-4-chloroamphetamine/f231SH8R">DOC</a></li></ul> <h2 id="external-links">External links</h2> <ul><li><a href="http://www.erowid.org/chemicals/2cc/2cc.shtml">Erowid 2C-C Vault</a></li> <li><a href="https://isomerdesign.com/pihkal/read/pk/22">pihkal.info: 2C-C</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. <a href="0-9630096-0-5" target="_blank">0-9630096-0-5</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>"S. 3187: Food and Drug Administration Safety and Innovation Act, Subtitle D-Synthetic Drugs". FDA. June 27, 2012. Archived from the original on July 4, 2012. Retrieved July 12, 2012. <a href="https://www.govtrack.us/congress/bills/112/s3187/text" target="_blank">https://www.govtrack.us/congress/bills/112/s3187/text</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. <a href="0-9630096-0-5" target="_blank">0-9630096-0-5</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>"Kᵢ Database". PDSP. 16 March 2025. Retrieved 16 March 2025. <a href="https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14697&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14669&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D=" target="_blank">https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14697&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14669&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D=</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Liu, Tiqing. "BindingDB BDBM50240789 2-(4-Chloro-2,5-dimethoxy-phenyl)-ethylamine::2-(4-chloro-2,5-dimethoxyphenyl)ethylamine::CHEMBL124733". BindingDB. Retrieved 16 March 2025. <a href="https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50240789" target="_blank">https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50240789</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. <a href="https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf" target="_blank">https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB (March 2014). "Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function" (PDF). Psychopharmacology (Berl). 231 (5): 875–888. doi:10.1007/s00213-013-3303-6. PMC 3945162. PMID 24142203. <a href="https://www.researchgate.net/profile/Michael-Forster-2/publication/258061356_Behavioral_and_neurochemical_pharmacology_of_six_psychoactive_substituted_phenethylamines_Mouse_locomotion_rat_drug_discrimination_and_in_vitro_receptor_and_transporter_binding_and_function/links/53d119a00cf2f7e53cfbcd68/Behavioral-and-neurochemical-pharmacology-of-six-psychoactive-substituted-phenethylamines-Mouse-locomotion-rat-drug-discrimination-and-in-vitro-receptor-and-transporter-binding-and-function.pdf" target="_blank">https://www.researchgate.net/profile/Michael-Forster-2/publication/258061356_Behavioral_and_neurochemical_pharmacology_of_six_psychoactive_substituted_phenethylamines_Mouse_locomotion_rat_drug_discrimination_and_in_vitro_receptor_and_transporter_binding_and_function/links/53d119a00cf2f7e53cfbcd68/Behavioral-and-neurochemical-pharmacology-of-six-psychoactive-substituted-phenethylamines-Mouse-locomotion-rat-drug-discrimination-and-in-vitro-receptor-and-transporter-binding-and-function.pdf</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101. <a href="https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=00665d67c36dcf1777989b70cc901c654420a0c7" target="_blank">https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=00665d67c36dcf1777989b70cc901c654420a0c7</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>Pottie E, Cannaert A, Stove CP (October 2020). "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. 94 (10): 3449–3460. Bibcode:2020ArTox..94.3449P. doi:10.1007/s00204-020-02836-w. hdl:1854/LU-8687071. PMID 32627074. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID 26791601. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep. 14: 101890. doi:10.1016/j.toxrep.2025.101890. PMC 11762925. PMID 39867514. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. <a href="https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf" target="_blank">https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><p>Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep. 14: 101890. doi:10.1016/j.toxrep.2025.101890. PMC 11762925. PMID 39867514. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925</a> <a href="#fnref:13" class="footnote-back-ref">↩</a></p></li> <li id="fn:14"><p>Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. <a href="https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf" target="_blank">https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf</a> <a href="#fnref:14" class="footnote-back-ref">↩</a></p></li> <li id="fn:15"><p>Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. <a href="https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf" target="_blank">https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf</a> <a href="#fnref:15" class="footnote-back-ref">↩</a></p></li> <li id="fn:16"><p>Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG (April 2021). "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Arch Toxicol. 95 (4): 1413–1429. doi:10.1007/s00204-021-02980-x. PMID 33515270. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:16" class="footnote-back-ref">↩</a></p></li> <li id="fn:17"><p>Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep. 14: 101890. doi:10.1016/j.toxrep.2025.101890. PMC 11762925. PMID 39867514. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925</a> <a href="#fnref:17" class="footnote-back-ref">↩</a></p></li> <li id="fn:18"><p>Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. <a href="https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf" target="_blank">https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf</a> <a href="#fnref:18" class="footnote-back-ref">↩</a></p></li> <li id="fn:19"><p>Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep. 14: 101890. doi:10.1016/j.toxrep.2025.101890. PMC 11762925. PMID 39867514. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925</a> <a href="#fnref:19" class="footnote-back-ref">↩</a></p></li> <li id="fn:20"><p>Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG (April 2021). "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Arch Toxicol. 95 (4): 1413–1429. doi:10.1007/s00204-021-02980-x. PMID 33515270. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:20" class="footnote-back-ref">↩</a></p></li> <li id="fn:21"><p>Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep. 14: 101890. doi:10.1016/j.toxrep.2025.101890. PMC 11762925. PMID 39867514. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925</a> <a href="#fnref:21" class="footnote-back-ref">↩</a></p></li> <li id="fn:22"><p>Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG (April 2021). "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Arch Toxicol. 95 (4): 1413–1429. doi:10.1007/s00204-021-02980-x. PMID 33515270. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:22" class="footnote-back-ref">↩</a></p></li> <li id="fn:23"><p>Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep. 14: 101890. doi:10.1016/j.toxrep.2025.101890. PMC 11762925. PMID 39867514. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925</a> <a href="#fnref:23" class="footnote-back-ref">↩</a></p></li> <li id="fn:24"><p>Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG (April 2021). "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Arch Toxicol. 95 (4): 1413–1429. doi:10.1007/s00204-021-02980-x. PMID 33515270. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:24" class="footnote-back-ref">↩</a></p></li> <li id="fn:25"><p>Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG (April 2021). "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Arch Toxicol. 95 (4): 1413–1429. doi:10.1007/s00204-021-02980-x. PMID 33515270. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:25" class="footnote-back-ref">↩</a></p></li> <li id="fn:26"><p>Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep. 14: 101890. doi:10.1016/j.toxrep.2025.101890. PMC 11762925. PMID 39867514. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925</a> <a href="#fnref:26" class="footnote-back-ref">↩</a></p></li> <li id="fn:27"><p>Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG (April 2021). "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Arch Toxicol. 95 (4): 1413–1429. doi:10.1007/s00204-021-02980-x. PMID 33515270. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:27" class="footnote-back-ref">↩</a></p></li> <li id="fn:28"><p>Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep. 14: 101890. doi:10.1016/j.toxrep.2025.101890. PMC 11762925. PMID 39867514. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925</a> <a href="#fnref:28" class="footnote-back-ref">↩</a></p></li> <li id="fn:29"><p>Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG (April 2021). "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Arch Toxicol. 95 (4): 1413–1429. doi:10.1007/s00204-021-02980-x. PMID 33515270. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:29" class="footnote-back-ref">↩</a></p></li> <li id="fn:30"><p>Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG (April 2021). "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Arch Toxicol. 95 (4): 1413–1429. doi:10.1007/s00204-021-02980-x. PMID 33515270. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:30" class="footnote-back-ref">↩</a></p></li> <li id="fn:31"><p>Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC 3657019. PMID 23494844. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657019" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657019</a> <a href="#fnref:31" class="footnote-back-ref">↩</a></p></li> <li id="fn:32"><p>Theobald DS, Maurer HH (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochem Pharmacol. 73 (2): 287–297. doi:10.1016/j.bcp.2006.09.022. PMID 17067556. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:32" class="footnote-back-ref">↩</a></p></li> <li id="fn:33"><p>Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC 3657019. PMID 23494844. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657019" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657019</a> <a href="#fnref:33" class="footnote-back-ref">↩</a></p></li> <li id="fn:34"><p>Theobald DS, Maurer HH (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochem Pharmacol. 73 (2): 287–297. doi:10.1016/j.bcp.2006.09.022. PMID 17067556. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:34" class="footnote-back-ref">↩</a></p></li> <li id="fn:35"><p>Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC 10851641. PMID 37982394. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10851641" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10851641</a> <a href="#fnref:35" class="footnote-back-ref">↩</a></p></li> <li id="fn:36"><p>Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC 10851641. PMID 37982394. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10851641" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10851641</a> <a href="#fnref:36" class="footnote-back-ref">↩</a></p></li> <li id="fn:37"><p>Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC 3657019. PMID 23494844. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657019" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657019</a> <a href="#fnref:37" class="footnote-back-ref">↩</a></p></li> <li id="fn:38"><p>"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015. <a href="https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html" target="_blank">https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html</a> <a href="#fnref:38" class="footnote-back-ref">↩</a></p></li> <li id="fn:39"><p>"Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016. <a href="http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php" target="_blank">http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php</a> <a href="#fnref:39" class="footnote-back-ref">↩</a></p></li> <li id="fn:40"><p>"20050026" (PDF). Archived (PDF) from the original on 2013-09-29. Retrieved 2017-03-24. <a href="https://www.notisum.se/rnp/sls/sfs/20050026.pdf" target="_blank">https://www.notisum.se/rnp/sls/sfs/20050026.pdf</a> <a href="#fnref:40" class="footnote-back-ref">↩</a></p></li> <li id="fn:41"><p>"Erowid 2C-C Vault : Legal Status". www.erowid.org. Archived from the original on 2014-06-02. <a href="http://www.erowid.org/chemicals/2cc/2cc_law.shtml" target="_blank">http://www.erowid.org/chemicals/2cc/2cc_law.shtml</a> <a href="#fnref:41" class="footnote-back-ref">↩</a></p></li> <li id="fn:42"><p>"Explore N-(2C-C)-Fentanyl | PiHKAL · info". isomerdesign.com. <a href="https://isomerdesign.com/PiHKAL/explore.php?domain=pk&id=14010" target="_blank">https://isomerdesign.com/PiHKAL/explore.php?domain=pk&id=14010</a> <a href="#fnref:42" class="footnote-back-ref">↩</a></p></li> </ol>