2C-I
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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
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| legal_AU = Schedule 9
| legal_BR = F2
| legal_CA = Schedule III
| legal_UK = Class A
| legal_US = Schedule I
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| 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
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 338297
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| synonyms =
| 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
| melting_point = 246
}}
2C-I, also known as 2,5-dimethoxy-4-iodophenethylamine, is a phenethylamine of the 2C family with psychedelic effects.{{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 }} It was first 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 (2C-I-NBOMe), nicknamed "Smiles" and "N-bomb" in the media.{{cite web |title=25I-NBOMe (2C-I-NBOMe): Fatalities / Deaths |url=http://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml}}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{{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
Use
In the early 2000s, 2C-I was sold in Dutch smart shops as a recreational drug after the drug 2C-B was banned.{{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 }}
According to the US Drug Enforcement Administration, 2C-I is taken orally or snorted in a powder form.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.]
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
2C-I is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = J Med Toxicol | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | url = }}{{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 = Biochem Pharmacol | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 | url = }} Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-I.{{Cite journal |vauthors=Halman A, Kong G, Sarris J, Perkins D |date=January 2024 |title=Drug-drug interactions involving classic psychedelics: A systematic review |journal=J Psychopharmacol |volume=38 |issue=1 |pages=3–18 |doi=10.1177/02698811231211219 |pmc=10851641 |pmid=37982394}} This may result in overdose and serious toxicity.
Pharmacology
=Pharmacodynamics=
2C-I acts as a serotonin receptor agonist. It produces psychedelic effects via serotonin 5-HT2A receptor activation.
It is inactive as a monoamine releasing agent and shows negligible activity as a monoamine reuptake inhibitor.
2C-I is a highly potent anti-inflammatory drug similarly to various other serotonergic psychedelics.{{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 }} However, 2C-I showed the highest anti-inflammatory potency of any other assessed drug in a large series in one study. It was more potent than (R)-DOI in terms of anti-inflammatory activity.
Chemistry
=Analogues and derivatives=
{{2C-I analogues and derivatives}}
Society and culture
=Legal status=
==Australia==
2C-I is a schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[https://www.comlaw.gov.au/Details/F2015L01534 Poisons Standard October 2015] 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".{{Cite web |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 |title=Poisons Act 1964 |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 }}
==Canada==
As of October 31, 2016, 2C-I is a controlled substance (Schedule III) in Canada.[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)]
==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.{{cite web|url=http://www.erowid.org/chemicals/2ci/2ci_law.shtml|title=Erowid 2C-I Vault : Legal Status}}
==Finland==
Illegal: scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs".{{cite web | url=https://finlex.fi/fi/lainsaadanto/2008/543 | title=Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista | 543/2008 | Lainsäädäntö | Finlex }}
==Sweden==
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 in their regulation LVFS 2004:3.{{cite web | url = http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf | title = Läkemedelsverkets författningssamling | language = sv}}
==United Kingdom==
In the United Kingdom, 2C-I is controlled as a Class A substance.
==United States==
As of July 9, 2012, in the United States 2C-I is a Schedule I substance under the Synthetic Drug Abuse Prevention Act of 2012, making possession, distribution and manufacture illegal. 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.{{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}}
See also
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 Erowid 2C-I Vault]
- [http://www.erowid.org/library/books_online/pihkal/pihkal033.shtml 2C-I Entry in PiHKAL]
- [http://pihkal.info/read.php?domain=pk&id=33 2C-I Entry in PiHKAL • info]
- [https://tripsitter.com/2ci/ 2C-I: An Obscure, But Powerful Research Chemical - Tripsitter]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{TAAR modulators}}
{{Phenethylamines}}
Category:Iodobenzene derivatives