View source for 2C-I

{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 477216266
| drug_name = 
| image = 2C-I2DACS.svg
| image_class = skin-invert-image
| width = 200px
| image2 = 2C-I-3d-sticks.png
| image_class2 = bg-transparent
| width2 = 200px

<!-- Clinical data -->
| pronounce = 
| tradename = 
| Drugs.com = 
| MedlinePlus = 
| licence_CA = 
| licence_EU = 
| DailyMedID = 
| licence_US = 
| pregnancy_AU = 
| pregnancy_category = 
| dependency_liability = 
| addiction_liability = 
| routes_of_administration = [[Oral administration|Oral]]<ref name="PiHKAL" /><ref name="Dean_2013" />
| class = [[Serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[agonist]]; [[Serotonin 5-HT2A receptor agonist|Serotonin 5-HT<sub>2A</sub> receptor agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]
| ATC_prefix = None
| ATC_suffix = 

<!-- Legal status -->
| legal_AU = Schedule 9
| legal_BR = F2
| legal_CA = Schedule III
| legal_UK = Class A
| legal_US = Schedule I
| legal_status = 

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = 
| onset = ≤40 minutes<ref name="PiHKAL" />
| elimination_half-life = 
| duration_of_action = 6–10 hours<ref name="PiHKAL" /><ref name="Dean_2013" />
| excretion = 

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 69587-11-7
| CAS_supplemental = 
| PubChem = 10267191
| PubChemSubstance = 
| IUPHAR_ligand = 
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8442670
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = S35362848V
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C22776
| ChEBI = 
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 338297
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = 4-Iodo-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-iodophenethylamine; 25I; Cimbi-88; 2C-DOI

<!-- Chemical data -->
| IUPAC_name = 2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine
| C=10 | H=14 | I=1 | N=1 | O=2
| SMILES = Ic1cc(OC)c(cc1OC)CCN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PQHQBRJAAZQXHL-UHFFFAOYSA-N

<!-- Physical data -->
| melting_point = 246
}}

'''2C-I''', also known as '''4-iodo-2,5-dimethoxyphenethylamine''', is a [[psychedelic drug]] of the [[substituted phenethylamine|phenethylamine]] and [[2C (psychedelics)|2C]] families.<ref name="PiHKAL">{{CitePiHKAL }} https://erowid.org/library/books_online/pihkal/pihkal033.shtml</ref><ref name="Anilanmert_2018" /><ref name="Dean_2013">{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = Journal of Medical Toxicology | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x }}</ref><ref name="Bosak_2013">{{cite journal | vauthors = Bosak A, LoVecchio F, Levine M | title = Recurrent seizures and serotonin syndrome following "2C-I" ingestion | journal = Journal of Medical Toxicology | volume = 9 | issue = 2 | pages = 196–198 | date = June 2013 | pmid = 23378129 | pmc = 3657032 | doi = 10.1007/s13181-013-0287-x }}</ref> It is taken [[oral administration|orally]].<ref name="PiHKAL" /><ref name="Dean_2013" />

2C-I was first [[chemical synthesis|synthesized]] and described by [[Alexander Shulgin]] in 1977<ref name="Shulgin_1978" /><ref name="Braun_1977" /> and was described in further detail in his 1991 book ''[[PiHKAL]]'' (''Phenethylamines I Have Known and Loved'').<ref name="PiHKAL" /> The drug is used [[recreational drug|recreationally]]. 2C-I is sometimes confused with other related psychedelic drugs such as [[25I-NBOMe|25I-NBOMe]] (NBOMe-2C-I), nicknamed "Smiles" and "N-bomb" in the media.<ref>{{cite web | title = 25I-NBOMe (2C-I-NBOMe): Fatalities / Deaths | url = http://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml }}</ref><ref name="weiss">Weiss, Piper (September 20, 2012). [http://shine.yahoo.com/healthy-living/2c-smiles-killer-drug-every-parent-know-234200299.html 2C-I or 'Smiles': The New Killer Drug Every Parent Should Know About.] ''[[Yahoo! News]]''</ref><ref name="Mackin_2012">{{cite web | vauthors = Mackin T | title = Dangerous synthetic drug making its way across the country. | date = October 9, 2012 | url = http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country | archive-url = https://web.archive.org/web/20121031163611/http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country | archive-date = October 31, 2012 }} [[WISH-TV]]</ref>

==Use and effects==
According to [[Alexander Shulgin]] in his book ''[[PiHKAL]]'' (''Phenethylamines I Have Known and Loved''), 2C-I has a dose range of 14 to 22{{nbsp}}mg [[oral administration|orally]] and a [[duration of action|duration]] of 6 to 10{{nbsp}}hours.<ref name="PiHKAL" /><ref name="Dean_2013" /> Its [[onset of action|onset]] is within 40{{nbsp}}minutes and peak effects occur after about 2{{nbsp}}hours.<ref name="PiHKAL" /> In addition to oral administration, 2C-I may also be [[insufflation (medicine)|insufflated]].<ref name="Reuters2011">Reuters (March 20, 2011). [https://web.archive.org/web/20160306161926/http://in.reuters.com/article/us-drugs-overdose-idINTRE72I3QT20110319 Synthetic drug, subject of proposed bans, kill teen.]</ref> The effects of 2C-I have been reported to include color enhancement, [[psychedelic visual]]s, [[emotion]]al enhancement, limited [[insight]]s, increased [[mental energy|energy]], enhanced conversation and [[honesty]], [[improved mood]], and sensual immersion.<ref name="PiHKAL" /> The sensual effects of 2C-I were described as different from and possibly less than those of [[2C-B]].<ref name="PiHKAL" />

== Interactions ==

{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

2C-I is [[drug metabolism|metabolized]] by the [[monoamine oxidase]] (MAO) [[enzyme]]s [[MAO-A]] and [[MAO-B]].<ref name="Dean_2013">{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = Journal of Medical Toxicology | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x }}</ref><ref name="Theobald_2007">{{cite journal | vauthors = Theobald DS, Maurer HH | title = Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series) | journal = Biochemical Pharmacology | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 }}</ref> [[Monoamine oxidase inhibitor]]s (MAOIs) such as [[phenelzine]], [[tranylcypromine]], [[moclobemide]], and [[selegiline]] may potentiate the effects of 2C-I.<ref name="Dean_2013" /><ref name="Theobald_2007" /><ref name="Halman_2024">{{cite journal | vauthors = Halman A, Kong G, Sarris J, Perkins D | title = Drug-drug interactions involving classic psychedelics: A systematic review | journal = Journal of Psychopharmacology | volume = 38 | issue = 1 | pages = 3–18 | date = January 2024 | pmid = 37982394 | pmc = 10851641 | doi = 10.1177/02698811231211219 }}</ref> This may result in [[overdose]] and serious [[toxicity]].<ref name="Halman_2024" /><ref name="Dean_2013" />

==Pharmacology==
===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>]] || 107–970 (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>]] || 56
|-
| [[5-HT1D receptor|5-HT<sub>1D</sub>]] || 40
|-
| [[5-HT1E receptor|5-HT<sub>1E</sub>]] || 131
|-
| [[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>]] || 9.3 (K<sub>i</sub>)<br />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>]] || 9.3–40 (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>]] || >10,000
|-
| [[5-HT4 receptor|5-HT<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT5A receptor|5-HT<sub>5A</sub>]] || >10,000
|-
| [[5-HT6 receptor|5-HT<sub>6</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT7 receptor|5-HT<sub>7</sub>]] || 1,316
|-
| [[Alpha-1A adrenergic receptor|α<sub>1A</sub>]] || 5,100–>10,000
|-
| [[Alpha-1B adrenergic receptor|α<sub>1B</sub>]] || >10,000
|-
| [[Alpha-1D adrenergic receptor|α<sub>1D</sub>]] || >10,000
|-
| [[Alpha-2A adrenergic receptor|α<sub>2A</sub>]] || 70–305
|-
| [[Alpha-2B adrenergic receptor|α<sub>2B</sub>]] || 608
|-
| [[Alpha-2C adrenergic receptor|α<sub>2C</sub>]] || 315
|-
| [[Beta-1 adrenergic receptor|β<sub>1</sub>]] || 4,512
|-
| [[Beta-2 adrenergic receptor|β<sub>2</sub>]] || >10,000
|-
| [[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>]] || 1,013–2,700
|-
| [[D3 receptor|D<sub>3</sub>]] || 989–5,000
|-
| [[D4 receptor|D<sub>4</sub>]] || 2,788
|-
| [[D5 receptor|D<sub>5</sub>]] || >10,000
|-
| [[H1 receptor|H<sub>1</sub>]] || 6,100
|-
| [[H2 receptor|H<sub>2</sub>]] || >10,000
|-
| [[H3 receptor|H<sub>3</sub>]] || >10,000
|-
| [[Muscarinic acetylcholine M1 receptor|M<sub>1</sub>]] || >10,000
|-
| [[Muscarinic acetylcholine M2 receptor|M<sub>2</sub>]] || 1,429
|-
| [[Muscarinic acetylcholine M3 receptor|M<sub>3</sub>]] || 950
|-
| [[Muscarinic acetylcholine M4 receptor|M<sub>4</sub>]] || 1,129
|-
| [[Muscarinic acetylcholine M5 receptor|M<sub>5</sub>]] || 2,151
|-
| [[I1 receptor|I<sub>1</sub>]] || {{Abbr|ND|No data}}
|-
| [[Sigma-1 receptor|σ<sub>1</sub>]] || >10,000
|-
| [[Sigma-2 receptor|σ<sub>2</sub>]] || 5,470
|-
| [[μ-Opioid receptor|MOR]] || 2,522
|-
| [[δ-Opioid receptor|DOR]] || {{Abbr|ND|No data}}
|-
| [[κ-Opioid receptor|KOR]] || >10,000
|-
| {{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:var(--background-color-notice-subtle,#eaecf0); color:inherit; 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 | date = 16 March 2025 | website = PDSP | 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="Rickli_2015">{{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 | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 }}</ref><ref name="Eshleman_2014">{{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 | volume = 231 | issue = 5 | pages = 875–888 | date = March 2014 | pmid = 24142203 | pmc = 3945162 | doi = 10.1007/s00213-013-3303-6 }}</ref><ref name="Ettrup_2011">{{cite journal | vauthors = Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM | title = Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers | journal = European Journal of Nuclear Medicine and Molecular Imaging | volume = 38 | issue = 4 | pages = 681–693 | date = April 2011 | pmid = 21174090 | doi = 10.1007/s00259-010-1686-8 }}</ref><ref name="Rudin_2022">{{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 | doi = 10.1096/fasebj.2022.36.S1.R2121 | article-number = fasebj.2022.36.S1.R2121 | issn = 0892-6638 | doi-access = free | url = https://www.researchgate.net/publication/360423277 }}</ref><ref name="Pottie_2020">{{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 = Archives of Toxicology | volume = 94 | issue = 10 | pages = 3449–3460 | date = October 2020 | pmid = 32627074 | doi = 10.1007/s00204-020-02836-w | hdl-access = free | bibcode = 2020ArTox..94.3449P | hdl = 1854/LU-8687071 }}</ref><br /><ref name="Wallach_2023">{{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-HT<sub>2A</sub> receptor signaling pathways associated with psychedelic potential | journal = Nature Communications | volume = 14 | issue = 1 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 | bibcode = 2023NatCo..14.8221W | article-number = 8221 }}</ref><ref name="AcunaCastillo_2002">{{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 = British Journal of Pharmacology | volume = 136 | issue = 4 | pages = 510–519 | date = June 2002 | pmid = 12055129 | pmc = 1573376 | doi = 10.1038/sj.bjp.0704747 }}</ref><ref name="Moya_2007">{{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 = The Journal of Pharmacology and Experimental Therapeutics | volume = 321 | issue = 3 | pages = 1054–1061 | date = June 2007 | pmid = 17337633 | doi = 10.1124/jpet.106.117507 }}</ref><ref name="Flanagan_2021" /><ref name="Wagmann_2019">{{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 Testing and Analysis | volume = 11 | issue = 2 | pages = 318–324 | date = February 2019 | pmid = 30188017 | doi = 10.1002/dta.2494 }}</ref><ref name="Simmler_2016">{{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 = The Journal of Pharmacology and Experimental Therapeutics | 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="Eshleman_2014" /><ref name="Rickli_2015" />

2C-I is a highly potent [[anti-inflammatory drug]] similarly to various other [[serotonergic psychedelic]]s.<ref name="Flanagan_2021">{{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 Pharmacology & Translational Science | volume = 4 | issue = 2 | pages = 488–502 | date = April 2021 | pmid = 33860179 | pmc = 8033619 | doi = 10.1021/acsptsci.0c00063 }}</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="Flanagan_2021" /> It was more potent than [[(R)-DOI|(''R'')-DOI]] in terms of anti-inflammatory activity.<ref name="Flanagan_2021" />

==Chemistry==
===Synthesis===
The [[chemical synthesis]] of 2C-I has been described.<ref name="PiHKAL" /><ref name="Shulgin_2011">{{cite book | vauthors = Shulgin A, Manning T, Daley P | title = [[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]] | location = Berkeley | volume = 1 | year = 2011 | publisher = [[Transform Press]] | isbn = 978-0-9630096-3-0 }}</ref>

===Analogues===
[[Structural analog|Analogue]]s of 2C-I include [[2C-H]] (2,5-DMPEA), [[2C-B]], [[2C-C]], [[DOI (drug)|DOI]], and [[25I-NBOMe]], among others.<ref name="PiHKAL" /><ref name="Trachsel_2013">{{cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | title = Phenethylamine: von der Struktur zur Funktion | location = Solothurn | year = 2013 | trans-title = Phenethylamines: From Structure to Function | edition = 1 | publisher = Nachtschatten-Verlag | series = Nachtschatten-Science | isbn = 978-3-03788-700-4 | oclc = 858805226 | url = https://books.google.com/books?id=-Us1kgEACAAJ | language = de | archive-url = https://archive.org/details/phenethylamine-von-der-struktur-zur-funktion-trachsel-lehmann-enzensperger-2013 | archive-date = 21 August 2025 }}</ref><ref name="Anilanmert_2018">{{cite book | vauthors = Anilanmert B, Yonar FÇ, Özdemir AA | chapter = 2C Derivatives of Phenylethylamines and Their Analysis | title = Chromatographic Techniques in the Forensic Analysis of Designer Drugs | pages = 277–304 | date = 31 January 2018 | doi = 10.1201/9781315313177-15 | publisher = CRC Press | publication-place = Boca Raton : Taylor & Francis/CRC Press, 2018. | series = Chromatographic science series | isbn = 978-1-315-31317-7 | url = https://www.taylorfrancis.com/books/9781315313160/chapters/10.1201/9781315313177-15 | access-date = 14 November 2025 }}</ref>

==History==
2C-I was first described in the [[scientific literature]] by [[Alexander Shulgin]] and colleagues in 1977.<ref name="Shulgin_1978">{{cite book | vauthors = Shulgin AT | veditors = Iversen LL, Iversen SD, Snyder SH | chapter = Psychotomimetic Drugs: Structure-Activity Relationships | title = Stimulants | pages = 243–333 | date = 1978 | doi = 10.1007/978-1-4757-0510-2_6 | publisher = Springer US | publication-place = Boston, MA | isbn = 978-1-4757-0512-6 | chapter-url = https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6 | url = https://books.google.com/books?id=h0_uBwAAQBAJ&pg=PA261 }}</ref><ref name="Braun_1977">{{cite journal | vauthors = Braun U, Shulgin AT, Braun G, Sargent T | title = Synthesis and body distribution of several iodine-131 labeled centrally acting drugs | journal = Journal of Medicinal Chemistry | volume = 20 | issue = 12 | pages = 1543–1546 | date = December 1977 | pmid = 592317 | doi = 10.1021/jm00222a001 }}</ref> Its properties and effects in humans were described by Shulgin in 1978.<ref name="Shulgin_1978" /> The drug was subsequently described in greater detail by Shulgin in his 1991 book ''[[PiHKAL]]'' (''Phenethylamines I Have Known and Loved'').<ref name="PiHKAL" /> In the early 2000s, 2C-I was sold in [[Netherlands|Dutch]] [[smart shop]]s as a [[recreational drug]] after the related drug [[2C-B]] was banned.<ref name="de_Boer_1999">{{cite journal | vauthors = de Boer D, Gijzels MJ, Bosman IJ, Maes RA | title = More data about the new psychoactive drug 2C-B | journal = Journal of Analytical Toxicology | volume = 23 | issue = 3 | pages = 227–228 | date = May–June 1999 | pmid = 10369336 | doi = 10.1093/jat/23.3.227 | df = dmy-all | doi-access = free }}</ref>

==Society and culture==
===Legal status===
[[File:2C-I Powder.jpg|thumb|right|200px|2C-I in powder form.]]

====Australia====
2C-I is a schedule 9 prohibited substance in Australia under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (October 2015).<ref name="Poisons Standard">[https://www.comlaw.gov.au/Details/F2015L01534 Poisons Standard October 2015]</ref> 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".<ref>{{Cite web | title = Poisons Act 1964 | url = http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument:26063P/$FILE/Poisons%20Act%201964%20-%20%5B09-f0-04%5D.pdf?OpenElement | access-date = 2015-12-13 | archive-url = https://web.archive.org/web/20151222191725/http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument%3A26063P/%24FILE/Poisons%20Act%201964%20-%20%5B09-f0-04%5D.pdf?OpenElement | archive-date = 2015-12-22 | url-status = dead }}</ref>

====Canada====
As of October 31, 2016, 2C-I is a controlled substance (Schedule III) in Canada.<ref>[http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)]</ref>

====European Union====
In December 2003, the [[European Council]] issued a binding order compelling all [[European Union]] member states to ban 2C-I within three months.<ref name="erowid-law">{{cite web | title = Erowid 2C-I Vault : Legal Status | url = http://www.erowid.org/chemicals/2ci/2ci_law.shtml }}</ref>

====Finland====
Illegal: scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs".<ref>{{cite web | title = Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista &#124; 543/2008 &#124; Lainsäädäntö &#124; Finlex | url = https://finlex.fi/fi/lainsaadanto/2008/543 }}</ref>

====Sweden====
[[Riksdag|''Sveriges riksdag'']] added 2C-I to schedule I (''"substances, plant materials and fungi which normally do not have medical use"'') as a narcotic on March 16, 2004, published by the [[Medical Products Agency (Sweden)|''Medical Products Agency'']] in their regulation LVFS 2004:3.<ref>{{cite web | title = Läkemedelsverkets författningssamling | url = http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf | language = sv }}</ref>

====United Kingdom====
In the United Kingdom, 2C-I is controlled as a [[Drugs controlled by the UK Misuse of Drugs Act|Class A]] substance.<ref name="erowid-law" />

====United States====
As of July 9, 2012, in the [[United States]] 2C-I is a [[Schedule I controlled substance|Schedule I]] substance under the [[Synthetic Drug Abuse Prevention Act of 2012]], making possession, distribution and manufacture illegal.<ref name="erowid-law" /> 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.<ref>{{cite web | title = H.R. 1254 (112th): Synthetic Drug Control Act of 2011 | url = https://www.govtrack.us/congress/bills/112/hr1254 | website = GovTrack | access-date = 30 September 2015 }}</ref>

== See also ==
* [[2C (psychedelics)]]

== References ==
{{Reflist}}

== External links ==
* [https://isomerdesign.com/pihkal/explore/33 2C-I - Isomer Design]
* [https://psychonautwiki.org/wiki/2C-I 2C-I - PsychonautWiki]
* [http://www.erowid.org/chemicals/2ci/2ci.shtml 2C-I - Erowid]
* [http://www.erowid.org/library/books_online/pihkal/pihkal033.shtml 2C-I - PiHKAL - Erowid]
* [http://pihkal.info/read.php?domain=pk&id=33 2C-I - PiHKAL - Isomer Design]
* [https://tripsitter.com/2ci/ 2C-I: An Obscure, But Powerful Research Chemical - TripSitter]

{{Psychedelics}}
{{Serotonin receptor modulators}}
{{TAAR modulators}}
{{Phenethylamines}}

[[Category:5-HT2A agonists]]
[[Category:5-HT2B agonists]]
[[Category:5-HT2C agonists]]
[[Category:2C (psychedelics)]]
[[Category:Anti-inflammatory agents]]
[[Category:Designer drugs]]
[[Category:Iodobenzene derivatives]]
[[Category:O-methylated phenols]]
[[Category:Psychedelic phenethylamines]]
[[Category:TAAR1 agonists]]