Editing 2C-I (section)

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{{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
| width2 = 200px

<!-- Clinical data -->
| pronounce = 
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| licence_CA = 
| licence_EU = 
| DailyMedID = 
| licence_US = 
| pregnancy_AU = 
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| routes_of_administration = 
| class = 
| ATC_prefix = 
| 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 = 
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<!-- 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
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<!-- 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 '''2,5-dimethoxy-4-iodophenethylamine''', is a [[substituted phenethylamine|phenethylamine]] of the [[2C (psychedelics)|2C family]] with [[psychedelic drug|psychedelic]] effects.<ref>{{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 was first [[chemical synthesis|synthesized]] by [[Alexander Shulgin]], and is described in Shulgin's book ''[[PiHKAL]]'' (1991).

The substance is consumed as a [[recreational drug]], and is circulated in the drug market in a powder form. 2C-I is sometimes confused with other related chemical substances such as [[25I-NBOMe|25I-NBOMe (2C-I-NBOMe)]], 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="mackin2012">{{cite web | vauthors = Mackin T | date = October 9, 2012 | url = http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country | title = Dangerous synthetic drug 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>