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2C-I
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<h2 id="use">Use</h2> <p>In the early 2000s, 2C-I was sold in Dutch <a href="/facts/Smart_shop/yQ1Tx5eC">smart shops</a> as a recreational drug after the drug <a href="/facts/2C-B/TerpnRXS">2C-B</a> was banned.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p><p>According to the US <a href="/facts/Drug_Enforcement_Administration/qGQpHNB8">Drug Enforcement Administration</a>, 2C-I is taken orally or <a href="/facts/Insufflation_(medicine)/dt9NPnl7">snorted</a> in a powder form.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</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-I is <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:7" href="#fn:7"><sup>7</sup></a><a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</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-I.<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><a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</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:12" href="#fn:12"><sup>12</sup></a><a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a> </p> <h2 id="pharmacology">Pharmacology</h2> <h3>Pharmacodynamics</h3> 2C-I 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>180–970 (Ki)4,900 (<a href="/facts/Half-maximal_effective_concentration/x7oD7ITx">EC50</a>Tooltip half-maximal effective concentration)102% (<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></td><td>ND</td></tr><tr><td><a href="/facts/5-HT1D_receptor/zzGzggdV">5-HT1D</a></td><td>ND</td></tr><tr><td><a href="/facts/5-HT1E_receptor/rBSqpDuD">5-HT1E</a></td><td>ND</td></tr><tr><td><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>3.5–9.3 (Ki)1.48–513 (EC50)17–93% (Emax)</td></tr><tr><td><a href="/facts/5-HT2B_receptor/Sy104fUR">5-HT2B</a></td><td>19.1–150 (EC50)70–101% (Emax)</td></tr><tr><td><a href="/facts/5-HT2C_receptor/RuyLstWf">5-HT2C</a></td><td>10–40 (Ki)0.46–537 (EC50)44–107% (Emax)</td></tr><tr><td><a href="/facts/5-HT3_receptor/7Qa2T8v3">5-HT3</a></td><td>ND</td></tr><tr><td><a href="/facts/5-HT4_receptor/aFSHbN6U">5-HT4</a></td><td>ND</td></tr><tr><td><a href="/facts/5-HT5A_receptor/Iclxf8po">5-HT5A</a></td><td>ND</td></tr><tr><td><a href="/facts/5-HT6_receptor/2QQJ7upp">5-HT6</a></td><td>ND</td></tr><tr><td><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>5,100</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>70</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>2,700</td></tr><tr><td><a href="/facts/D3_receptor/e1L1KnJq">D3</a></td><td>5,000</td></tr><tr><td><a href="/facts/D4_receptor/26otIqul">D4</a>, <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>6,100</td></tr><tr><td><a href="/facts/Trace_amine-associated_receptor_1/Xf3Qpjtw">TAAR1</a>Tooltip Trace amine-associated receptor 1</td><td>3,300 (Ki) (mouse)120 (Ki) (rat)2,400 (EC50) (mouse)190 (EC50) (rat)>10,000 (EC50) (human)51% (Emax) (mouse)50% (Emax) (rat)</td></tr><tr><td><a href="/facts/Serotonin_transporter/VPh5wtCy">SERT</a>Tooltip Serotonin transporter</td><td>950–4,900 (Ki)5,600–13,000 (<a href="/facts/Half-maximal_inhibitory_concentration/zdz6qVBP">IC50</a>Tooltip half-maximal inhibitory concentration)IA (EC50)</td></tr><tr><td><a href="/facts/Norepinephrine_transporter/532N8LIg">NET</a>Tooltip Norepinephrine transporter</td><td>15,000 (Ki)22,000 (IC50)IA (EC50)</td></tr><tr><td><a href="/facts/Dopamine_transporter/V9I2Uy1p">DAT</a>Tooltip Dopamine transporter</td><td>>30,000 (Ki)126,000 (IC50)IA (EC50)</td></tr><tr><td><a href="/facts/Monoamine_oxidase_A/VXqw1LUU">MAO-A</a>Tooltip Monoamine oxidase A</td><td>125,000 (IC50)</td></tr><tr><td><a href="/facts/Monoamine_oxidase_B/wa0xq7KL">MAO-B</a>Tooltip Monoamine oxidase B</td><td>55,000 (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:14" href="#fn:14"><sup>14</sup></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><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><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><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><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></td></tr></tbody></table> <p>2C-I acts as a <a href="/facts/Serotonin_receptor/D6656QzQ">serotonin receptor</a> <a href="/facts/Agonist/nz8U5NNp">agonist</a>. It produces <a href="/facts/Psychedelic_drug/aj9GNANW">psychedelic</a> effects via serotonin <a href="/facts/5-HT2A_receptor/YfTglQKQ">5-HT2A receptor</a> activation. </p><p>It is inactive as a <a href="/facts/Monoamine_releasing_agent/JwSvmyR8">monoamine releasing agent</a> and shows negligible activity as a <a href="/facts/Monoamine_reuptake_inhibitor/NKWd6IvY">monoamine reuptake inhibitor</a>.<a class="footnote-ref" id="fnref:25" href="#fn:25"><sup>25</sup></a><a class="footnote-ref" id="fnref:26" href="#fn:26"><sup>26</sup></a> </p><p>2C-I is a highly potent <a href="/facts/Anti-inflammatory_drug/W27poSUd">anti-inflammatory drug</a> similarly to various other <a href="/facts/Serotonergic_psychedelic/oyp10dgE">serotonergic psychedelics</a>.<a class="footnote-ref" id="fnref:27" href="#fn:27"><sup>27</sup></a> However, 2C-I showed the highest anti-inflammatory <a href="/facts/Potency_(pharmacology)/D38FDyPh">potency</a> of any other assessed drug in a large series in one study.<a class="footnote-ref" id="fnref:28" href="#fn:28"><sup>28</sup></a> It was more potent than <a href="/facts/(R)-DOI/gUnTooCA">(<i>R</i>)-DOI</a> in terms of anti-inflammatory activity.<a class="footnote-ref" id="fnref:29" href="#fn:29"><sup>29</sup></a> </p> <h2 id="chemistry">Chemistry</h2> <h3>Analogues and derivatives</h3> <p><a href="/facts/2%2c5-Dimethoxy-4-iodoamphetamine/gUnTooCA">DOI</a> </p> <p>Analogues and derivatives of 2C-I: </p><p>25I-NB*: </p> <ul><li><a href="/facts/25I-NBF/CcaHeD12">25I-NBF</a></li> <li><a href="/facts/25I-NBMD/FdVWDxw6">25I-NBMD</a></li> <li><a href="/facts/25I-NB34MD/lA4oTrSY">25I-NB34MD</a></li> <li><a href="/facts/25I-NBOH/PQMYvj79">25I-NBOH</a></li> <li><a href="/facts/25I-NBOMe/eA2kwDRN">25I-NBOMe</a> (NBOMe-2CI)</li> <li><a href="/facts/25I-NB3OMe/DC2PghGE">25I-NB3OMe</a></li> <li><a href="/facts/25I-NB4OMe/JFtEcD8y">25I-NB4OMe</a></li></ul> <p><a href="/facts/N-(2C)-fentanyl/pJrN2yB2">N-(2C)-fentanyl</a>: </p> <ul><li>N-(2C-I) fentanyl<a class="footnote-ref" id="fnref:30" href="#fn:30"><sup>30</sup></a></li></ul> <h2 id="society-and-culture">Society and culture</h2> <h3>Legal status</h3> <h4>Australia</h4> <p>2C-I is a schedule 9 prohibited substance in Australia under the <a href="/facts/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons/Lna99E1T">Poisons Standard</a> (October 2015).<a class="footnote-ref" id="fnref:31" href="#fn:31"><sup>31</sup></a> A schedule 9 drug is outlined in the Poisons Act 1964 as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO".<a class="footnote-ref" id="fnref:32" href="#fn:32"><sup>32</sup></a> </p> <h4>Canada</h4> <p>As of October 31, 2016, 2C-I is a controlled substance (Schedule III) in Canada.<a class="footnote-ref" id="fnref:33" href="#fn:33"><sup>33</sup></a> </p> <h4>European Union</h4> <p>In December 2003, the <a href="/facts/European_Council/QLJLlbkt">European Council</a> issued a binding order compelling all <a href="/facts/European_Union/6GYcR8qM">European Union</a> member states to ban 2C-I within three months.<a class="footnote-ref" id="fnref:34" href="#fn:34"><sup>34</sup></a> </p> <h4>Sweden</h4> <p><a href="/facts/Riksdag/uarwUozH"><i>Sveriges riksdag</i></a> added 2C-I to schedule I (<i>"substances, plant materials and fungi which normally do not have medical use"</i>) as a narcotic on March 16, 2004, published by the <a href="/facts/Medical_Products_Agency_(Sweden)/TAAAhvnH"><i>Medical Products Agency</i></a> in their regulation LVFS 2004:3.<a class="footnote-ref" id="fnref:35" href="#fn:35"><sup>35</sup></a> </p> <h4>United Kingdom</h4> <p>In the United Kingdom, 2C-I is controlled as a <a href="/facts/Drugs_controlled_by_the_UK_Misuse_of_Drugs_Act/SVEfw54x">Class A</a> substance.<a class="footnote-ref" id="fnref:36" href="#fn:36"><sup>36</sup></a> </p> <h4>United States</h4> <p>As of July 9, 2012, in the <a href="/facts/United_States/P0sCdLe5">United States</a> 2C-I is a <a href="/facts/Schedule_I_controlled_substance/8laeNsgD">Schedule I</a> substance under the <a href="/facts/Synthetic_Drug_Abuse_Prevention_Act_of_2012/M9MUzkva">Synthetic Drug Abuse Prevention Act of 2012</a>, making possession, distribution and manufacture illegal.<a class="footnote-ref" id="fnref:37" href="#fn:37"><sup>37</sup></a> A previous bill, introduced in March 2011, that would have done the same passed the House of Representatives, but was not passed by the Senate.<a class="footnote-ref" id="fnref:38" href="#fn:38"><sup>38</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Recreational_drug_use/eoBD3vKn">Recreational drug use</a></li></ul> <h2 id="external-links">External links</h2> <ul><li><a href="https://isomerdesign.com/pihkal/explore/33">2C-I - Isomer Design</a></li> <li><a href="https://psychonautwiki.org/wiki/2C-I">2C-I - PsychonautWiki</a></li> <li><a href="http://www.erowid.org/chemicals/2ci/2ci.shtml">Erowid 2C-I Vault</a></li> <li><a href="http://www.erowid.org/library/books_online/pihkal/pihkal033.shtml">2C-I Entry in PiHKAL</a></li> <li><a href="http://pihkal.info/read.php?domain=pk&id=33">2C-I Entry in PiHKAL • info</a></li> <li><a href="https://tripsitter.com/2ci/">2C-I: An Obscure, But Powerful Research Chemical - Tripsitter</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Bosak A, LoVecchio F, Levine M (June 2013). "Recurrent seizures and serotonin syndrome following "2C-I" ingestion". Journal of Medical Toxicology. 9 (2): 196–198. doi:10.1007/s13181-013-0287-x. PMC 3657032. PMID 23378129. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657032" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657032</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>"25I-NBOMe (2C-I-NBOMe): Fatalities / Deaths". <a href="http://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml" target="_blank">http://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Weiss, Piper (September 20, 2012). 2C-I or 'Smiles': The New Killer Drug Every Parent Should Know About. Yahoo! News <a href="http://shine.yahoo.com/healthy-living/2c-smiles-killer-drug-every-parent-know-234200299.html" target="_blank">http://shine.yahoo.com/healthy-living/2c-smiles-killer-drug-every-parent-know-234200299.html</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Mackin T (October 9, 2012). "Dangerous synthetic drug making its way across the country". Archived from the original on October 31, 2012. WISH-TV <a href="https://web.archive.org/web/20121031163611/http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country" target="_blank">https://web.archive.org/web/20121031163611/http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>de Boer D, Gijzels MJ, Bosman IJ, Maes RA (May–June 1999). "More data about the new psychoactive drug 2C-B". Journal of Analytical Toxicology. 23 (3): 227–228. doi:10.1093/jat/23.3.227. PMID 10369336. <a href="https://doi.org/10.1093%2Fjat%2F23.3.227" target="_blank">https://doi.org/10.1093%2Fjat%2F23.3.227</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Reuters (March 20, 2011). Synthetic drug, subject of proposed bans, kill teen. <a href="https://web.archive.org/web/20160306161926/http://in.reuters.com/article/us-drugs-overdose-idINTRE72I3QT20110319" target="_blank">https://web.archive.org/web/20160306161926/http://in.reuters.com/article/us-drugs-overdose-idINTRE72I3QT20110319</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><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:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><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:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><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:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><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:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><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:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><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:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><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. 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