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===Pharmacodynamics=== {| class="wikitable floatleft" style="font-size:small;" |+ {{Nowrap|2C-I activities}} |- ! [[Biological target|Target]] !! [[Affinity (pharmacology)|Affinity]] (K<sub>i</sub>, nM) |- | [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 180–970 (K<sub>i</sub>)<br />4,900 ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}})<br />102% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}}) |- | [[5-HT1B receptor|5-HT<sub>1B</sub>]] || {{Abbr|ND|No data}} |- | [[5-HT1D receptor|5-HT<sub>1D</sub>]] || {{Abbr|ND|No data}} |- | [[5-HT1E receptor|5-HT<sub>1E</sub>]] || {{Abbr|ND|No data}} |- | [[5-HT1F receptor|5-HT<sub>1F</sub>]] || {{Abbr|ND|No data}} |- | [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 3.5–9.3 (K<sub>i</sub>)<br />1.48–513 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />17–93% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |- | [[5-HT2B receptor|5-HT<sub>2B</sub>]] || 19.1–150 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />70–101% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |- | [[5-HT2C receptor|5-HT<sub>2C</sub>]] || 10–40 (K<sub>i</sub>)<br />0.46–537 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />44–107% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) |- | [[5-HT3 receptor|5-HT<sub>3</sub>]] || {{Abbr|ND|No data}} |- | [[5-HT4 receptor|5-HT<sub>4</sub>]] || {{Abbr|ND|No data}} |- | [[5-HT5A receptor|5-HT<sub>5A</sub>]] || {{Abbr|ND|No data}} |- | [[5-HT6 receptor|5-HT<sub>6</sub>]] || {{Abbr|ND|No data}} |- | [[5-HT7 receptor|5-HT<sub>7</sub>]] || {{Abbr|ND|No data}} |- | [[Alpha-1A adrenergic receptor|α<sub>1A</sub>]] || 5,100 |- | [[Alpha-1B adrenergic receptor|α<sub>1B</sub>]], [[Alpha-1D adrenergic receptor|α<sub>1D</sub>]] || {{Abbr|ND|No data}} |- | [[Alpha-2A adrenergic receptor|α<sub>2A</sub>]] || 70 |- | [[Alpha-2B adrenergic receptor|α<sub>2B</sub>]], [[Alpha-2C adrenergic receptor|α<sub>2C</sub>]] || {{Abbr|ND|No data}} |- | [[Beta-1 adrenergic receptor|β<sub>1</sub>]]–[[Beta-3 adrenergic receptor|β<sub>3</sub>]] || {{Abbr|ND|No data}} |- | [[D1 receptor|D<sub>1</sub>]] || 13,000 |- | [[D2 receptor|D<sub>2</sub>]] || 2,700 |- | [[D3 receptor|D<sub>3</sub>]] || 5,000 |- | [[D4 receptor|D<sub>4</sub>]], [[D5 receptor|D<sub>5</sub>]] || {{Abbr|ND|No data}} |- | [[H1 receptor|H<sub>1</sub>]] || 6,100 |- | {{Abbrlink|TAAR1|Trace amine-associated receptor 1}} || 3,300 (K<sub>i</sub>) (mouse)<br />120 (K<sub>i</sub>) (rat)<br />2,400 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (mouse)<br />190 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (rat)<br />>10,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (human)<br />51% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (mouse)<br />50% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (rat) |- | {{Abbrlink|SERT|Serotonin transporter}} || 950–4,900 (K<sub>i</sub>)<br />5,600–13,000 ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />{{Abbr|IA|Inactive}} ({{Abbr|EC<sub>50</sub>|half-maximal inhibitory concentration}}) |- | {{Abbrlink|NET|Norepinephrine transporter}} || 15,000 (K<sub>i</sub>)<br />22,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />{{Abbr|IA|Inactive}} ({{Abbr|EC<sub>50</sub>|half-maximal inhibitory concentration}}) |- | {{Abbrlink|DAT|Dopamine transporter}} || >30,000 (K<sub>i</sub>)<br />126,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />{{Abbr|IA|Inactive}} ({{Abbr|EC<sub>50</sub>|half-maximal inhibitory concentration}}) |- | {{Abbrlink|MAO-A|Monoamine oxidase A}} || 125,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}}) |- | {{Abbrlink|MAO-B|Monoamine oxidase B}} || 55,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}}) |- class="sortbottom" | colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. '''Refs:''' <ref name="PDSPKiDatabase">{{cite web | title=Kᵢ Database | website=PDSP | date=16 March 2025 | url=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=12953&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14673&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D= | access-date=16 March 2025}}</ref><ref name="RickliLuethiReinisch2015">{{cite journal | vauthors = Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME | title = Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs) | journal = Neuropharmacology | volume = 99 | issue = | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 | url = 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}}</ref><ref name="EshlemanForsterWolfrum2014">{{cite journal | vauthors = Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB | title = Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function | journal = Psychopharmacology (Berl) | volume = 231 | issue = 5 | pages = 875–888 | date = March 2014 | pmid = 24142203 | pmc = 3945162 | doi = 10.1007/s00213-013-3303-6 | url = https://www.researchgate.net/publication/258061356}}</ref><ref name="RudinLuethiHoener2022">{{cite journal | vauthors = Rudin D, Luethi D, Hoener MC, Liechti ME | title=Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues | journal=The FASEB Journal | volume=36 | issue=S1 | date=2022 | issn=0892-6638 | doi=10.1096/fasebj.2022.36.S1.R2121 | doi-access=free | url=https://www.researchgate.net/publication/360423277}}</ref><ref name="PottieCannaertStove2020">{{cite journal | vauthors = Pottie E, Cannaert A, Stove CP | title = In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor | journal = Arch Toxicol | volume = 94 | issue = 10 | pages = 3449–3460 | date = October 2020 | pmid = 32627074 | doi = 10.1007/s00204-020-02836-w | bibcode = 2020ArTox..94.3449P | url = | hdl = 1854/LU-8687071 | hdl-access = free }}</ref><br /><ref name="WallachCaoCalkins2023">{{cite journal | vauthors = Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nat Commun | volume = 14 | issue = 1 | pages = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 }}</ref><ref name="Acuña-CastilloVillalobosMoya2002">{{cite journal | vauthors = Acuña-Castillo C, Villalobos C, Moya PR, Sáez P, Cassels BK, Huidobro-Toro JP | title = Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors | journal = Br J Pharmacol | volume = 136 | issue = 4 | pages = 510–519 | date = June 2002 | pmid = 12055129 | pmc = 1573376 | doi = 10.1038/sj.bjp.0704747 | url = }}</ref><ref name="MoyaBergGutiérrez-Hernandez2007">{{cite journal | vauthors = Moya PR, Berg KA, Gutiérrez-Hernandez MA, Sáez-Briones P, Reyes-Parada M, Cassels BK, Clarke WP | title = Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors | journal = J Pharmacol Exp Ther | volume = 321 | issue = 3 | pages = 1054–1061 | date = June 2007 | pmid = 17337633 | doi = 10.1124/jpet.106.117507 | url = https://repositorio.uchile.cl/bitstream/handle/2250/119461/Moya_Pablo_R.pdf}}</ref><ref name="FlanaganBillacLandry2021" /><ref name="WagmannBrandtStratford2019">{{cite journal | vauthors = Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR | title = Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases | journal = Drug Test Anal | volume = 11 | issue = 2 | pages = 318–324 | date = February 2019 | pmid = 30188017 | doi = 10.1002/dta.2494 | url = }}</ref><ref name="SimmlerBuchyChaboz2016">{{cite journal | vauthors = Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME | title = In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1 | journal = J Pharmacol Exp Ther | volume = 357 | issue = 1 | pages = 134–144 | date = April 2016 | pmid = 26791601 | doi = 10.1124/jpet.115.229765 | url = https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA| archive-url = https://web.archive.org/web/20250509235235/https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA | archive-date = 9 May 2025 }}</ref> |} 2C-I acts as a [[serotonin receptor]] [[agonist]]. It produces [[psychedelic drug|psychedelic]] effects via serotonin [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] activation. It is inactive as a [[monoamine releasing agent]] and shows negligible activity as a [[monoamine reuptake inhibitor]].<ref name="EshlemanForsterWolfrum2014" /><ref name="RickliLuethiReinisch2015" /> 2C-I is a highly potent [[anti-inflammatory drug]] similarly to various other [[serotonergic psychedelic]]s.<ref name="FlanaganBillacLandry2021">{{cite journal | vauthors = Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD | title = Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore | journal = ACS Pharmacol Transl Sci | volume = 4 | issue = 2 | pages = 488–502 | date = April 2021 | pmid = 33860179 | pmc = 8033619 | doi = 10.1021/acsptsci.0c00063 | url = https://www.researchgate.net/publication/360537036 }}</ref> However, 2C-I showed the highest anti-inflammatory [[potency (pharmacology)|potency]] of any other assessed drug in a large series in one study.<ref name="FlanaganBillacLandry2021" /> It was more potent than [[(R)-DOI|(''R'')-DOI]] in terms of anti-inflammatory activity.<ref name="FlanaganBillacLandry2021" />
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