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{{Refimprove|date=July 2010}}
{{chembox
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| ImageFile1 = 2C-I2DACS.svg
| ImageFile1 = 2C-I2DACS.svg
| ImageSize1 = 150px
| ImageSize1 = 150px
| ImageClass1 = skin-invert
| ImageFileL2 = 2C-I-3d-sticks.png
| ImageFileL2 = 2C-I-3d-sticks.png
| ImageFileR2 = 2C-I animation.gif
| ImageFileR2 = 2C-I animation.gif
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| UNII_Ref = {{fdacite|changed|FDA}}
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = S35362848V
| UNII = S35362848V
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C22776
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8442670
| ChemSpiderID = 8442670
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| FlashPt =
| FlashPt =
| AutoignitionPt =
| AutoignitionPt =
}}
| Section6 = {{Chembox Pharmacology
| Legal_status =
| Legal_AU = Schedule 9
| Legal_BR = F2
| Legal_CA = Schedule III
| Legal_UK = Class A
| Legal_US = Schedule I
}}
}}
}}
}}


'''2C-I (2,5-Dimethoxy-4-iodophenethylamine)''' is a [[phenethylamine]] of the [[2C (psychedelics)|2C family]] with [[psychedelic drug|psychedelic]] properties, primarily used as a recreational drug.<ref>{{cite journal |last1=Bosak |first1=Adam |last2=LoVecchio |first2=Frank |last3=Levine |first3=Michael |title=Recurrent Seizures and Serotonin Syndrome Following "2C-I" Ingestion |journal=Journal of Medical Toxicology |date=June 2013 |volume=9 |issue=2 |pages=196–198 |doi=10.1007/s13181-013-0287-x |pmid=23378129 |pmc=3657032 |issn=1556-9039}}</ref> It was first synthesized by [[Alexander Shulgin]], and is described in Shulgin's book ''[[PiHKAL]]'' (1991).
⚫
'''2C-I''' is a [[psychedelic drug|psychedelic]] [[phenethylamine]] of the [[2C (psychedelics)|2C family]].<ref>{{cite web|url=http://www.erowid.org/library/books_online/pihkal/pihkal033.shtml|title=Erowid Online Books : "PIHKAL" - #33 2C-I|publisher=}}</ref> It was first synthesized by [[Alexander Shulgin]] and described in his 1991 book ''[[PiHKAL|PiHKAL: A Chemical Love Story]]''. The drug is used recreationally for its psychedelic and [[empathogen-entactogen|entactogenic]] effects and is sometimes confused for the analog [[25I-NBOMe]], nicknamed "Smiles," 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">Mackin, Teresa (October 9, 2012). [http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country Dangerous synthetic drug making its way across the country.] {{webarchive |url=https://web.archive.org/web/20121031163611/http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country |date=October 31, 2012 }} [[WISH-TV]]</ref>


⚫
The substance is consumed as a [[recreational drug]], and is circulated in the [[Illicit drug market|illicit market]] in a powder or liquid 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">Mackin, Teresa (October 9, 2012). [http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country Dangerous synthetic drug making its way across the country.] {{webarchive|url=https://web.archive.org/web/20121031163611/http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country|date=October 31, 2012}} [[WISH-TV]]</ref>
==Recreational use==

== Patterns of use ==
[[File:2C-I Powder.jpg|thumb|the drug 2C-I in powder form]]
[[File:2C-I Powder.jpg|thumb|the drug 2C-I in powder form]]
In the early 2000s, 2C-I was sold in Dutch [[smart shop]]s after the drug [[2C-B]] was banned.<ref name="Netherlands 2c-b emergence">{{cite journal|last=de Boer|title=More Data About the New Psychoactive Drug 2C-B|journal=Journal of Analytical Toxicology|date=May–June 1999|volume=23|issue=3|pages=227–228|doi=10.1093/jat/23.3.227|url=http://intl-jat.oxfordjournals.org/content/23/3/227.full.pdf|accessdate=16 August 2012|pmid=10369336|display-authors=etal}}</ref>
In the early 2000s, 2C-I was sold in Dutch [[smart shop]]s as a recreational drug after the drug [[2C-B]] was banned.<ref name="Netherlands 2c-b emergence">{{cite journal|last=de Boer|title=More Data About the New Psychoactive Drug 2C-B|journal=Journal of Analytical Toxicology|date=May–June 1999|volume=23|issue=3|pages=227–228|doi=10.1093/jat/23.3.227|pmid=10369336|display-authors=etal|df=dmy-all|doi-access=free}}</ref>


According to the US [[Drug Enforcement Administration]], 2C-I is taken orally or [[Insufflation (medicine)|snorted]] in a powder form.<ref name="reuters2011">Reuters (March 20, 2011). [http://in.reuters.com/article/2011/03/19/us-drugs-overdose-idINTRE72I3QT20110319 Synthetic drug, subject of proposed bans, kill teen.]</ref>
According to the US [[Drug Enforcement Administration]], 2C-I is taken orally or [[Insufflation (medicine)|snorted]] in a powder form.<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>


==Drug prohibition laws==
==Drug prohibition laws==
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===European Union===
===European Union===


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


===Canada===
===Canada===
As of October 31st, 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</ref>
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>


===Australia===
===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">Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534</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>Poisons Act 1964 http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument:26063P/$FILE/Poisons%20Act%201964%20-%20%5B09-f0-04%5D.pdf?OpenElement</ref>
2C-I is a schedule 9 prohibited substance in Australia under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (October 2015).<ref name="Poisons Standard">[https://www.comlaw.gov.au/Details/F2015L01534 Poisons Standard October 2015]</ref> A schedule 9 drug is outlined in the [[Poisons Act 1964]] as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO".<ref>{{Cite web |url=http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument:26063P/$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 }}</ref>


===Sweden===
===Sweden===
[[Riksdag|''Sveriges riksdag'']] added 2C-I to schedule I (''"substances, plant materials and fungi which normally do not have medical use"'') as narcotics in Sweden as of Mar 16, 2004, published by [[Medical Products Agency (Sweden)|''Medical Products Agency'']] in their regulation '''LVFS 2004:3''' listed as '''4-jodo-2,5-dimetoxifenetylamin (2C-I)'''.<ref>http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf</ref>
[[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 | url = http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf | title = Läkemedelsverkets författningssamling | language = sv}}</ref>


===United Kingdom===
===United Kingdom===
Controlled as a [[Drugs controlled by the UK Misuse of Drugs Act|Class A]] substance.<ref name="erowid-law" />
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===
===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|accessdate=30 September 2015}}</ref>
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>


==Analogues and derivatives==
⚫
==See also==
⚫
[[2,5-Dimethoxy-4-iodoamphetamine|DOI]]


{{2C-I analogues and derivatives}}
* [[Empathogen-entactogen]]

* [[Phenethylamine]]
⚫
==See also==
* [[Psychedelic drug]]
* [[Recreational drug use]]
* [[Recreational drug use]]
* [[Alexander Shulgin]]
* [[2C family]]
⚫
* [[2,5-Dimethoxy-4-iodoamphetamine|DOI]]
* [[2C-B]]
* [[2C-T-2]]
* [[2C-T-7]]


==References==
==References==
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==External links==
==External links==
* [http://www.erowid.org/chemicals/2ci/2ci.shtml Erowid 2C-I Vault]
* [http://www.erowid.org/chemicals/2ci/2ci.shtml Erowid 2C-I Vault]
* [http://shulgin.es/una-experiencia-con-2c-i-en-aquisgran/ Una experiencia con 2C-I de los Shulgin] (In Spanish)
* [http://shulgin.es/una-experiencia-con-2c-i-en-aquisgran/ Una experiencia con 2C-I de los Shulgin] {{Webarchive|url=https://web.archive.org/web/20210419111846/https://shulgin.es/una-experiencia-con-2c-i-en-aquisgran/ |date=2021-04-19 }} (In Spanish)
* [http://www.erowid.org/library/books_online/pihkal/pihkal033.shtml 2C-I Entry in PiHKAL]
* [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]
* [http://pihkal.info/read.php?domain=pk&id=33 2C-I Entry in PiHKAL • info]


{{2Cs}}
{{Hallucinogens}}
{{Hallucinogens}}
{{Serotonergics}}
{{Serotonergics}}
{{Phenethylamines}}
{{Phenethylamines}}
{{PiHKAL}}


[[Category:2C (psychedelics)]]
[[Category:2C (psychedelics)]]
[[Category:Designer drugs]]
[[Category:Designer drugs]]
[[Category:Iodoarenes]]
[[Category:Iodobenzene derivatives]]
[[Category:Phenol ethers]]
[[Category:O-methylated phenols]]
[[Category:Psychedelic phenethylamines]]

Latest revision as of 01:57, 24 December 2024

2C-I
Names
Preferred IUPAC name
2-(4-Iodo-2,5-dimethoxyphenyl)ethan-1-amine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.217.507 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 checkY
    Key: PQHQBRJAAZQXHL-UHFFFAOYSA-N checkY
  • InChI=1/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3
    Key: PQHQBRJAAZQXHL-UHFFFAOYAK
  • Ic1cc(OC)c(cc1OC)CCN
Properties
C10H14INO2
Molar mass 307.131 g·mol−1
Melting point 246 °C (475 °F; 519 K)
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

2C-I (2,5-Dimethoxy-4-iodophenethylamine) is a phenethylamine of the 2C family with psychedelic properties, primarily used as a recreational drug.[1] 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 illicit market in a powder or liquid 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.[2][3][4]

Patterns of use

[edit]
the drug 2C-I in powder form

In the early 2000s, 2C-I was sold in Dutch smart shops as a recreational drug after the drug 2C-B was banned.[5]

According to the US Drug Enforcement Administration, 2C-I is taken orally or snorted in a powder form.[6]

Drug prohibition laws

[edit]

European Union

[edit]

In December 2003, the European Council issued a binding order compelling all European Union member states to ban 2C-I within three months.[7]

Canada

[edit]

As of October 31, 2016, 2C-I is a controlled substance (Schedule III) in Canada.[8]

Australia

[edit]

2C-I is a schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[9] 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".[10]

Sweden

[edit]

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.[11]

United Kingdom

[edit]

In the United Kingdom, 2C-I is controlled as a Class A substance.[7]

United States

[edit]

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.[7] 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.[12]

Analogues and derivatives

[edit]

DOI

Analogues and derivatives of 2C-I:

25I-NB*:

N-(2C)-fentanyl:

See also

[edit]

References

[edit]
  1. ^ Bosak, Adam; LoVecchio, Frank; Levine, Michael (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. ISSN 1556-9039. PMC 3657032. PMID 23378129.
  2. ^ "25I-NBOMe (2C-I-NBOMe): Fatalities / Deaths".
  3. ^ Weiss, Piper (September 20, 2012). 2C-I or 'Smiles': The New Killer Drug Every Parent Should Know About. Yahoo! News
  4. ^ Mackin, Teresa (October 9, 2012). Dangerous synthetic drug making its way across the country. Archived October 31, 2012, at the Wayback Machine WISH-TV
  5. ^ de Boer; et al. (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.
  6. ^ Reuters (March 20, 2011). Synthetic drug, subject of proposed bans, kill teen.
  7. ^ a b c "Erowid 2C-I Vault : Legal Status".
  8. ^ Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)
  9. ^ Poisons Standard October 2015
  10. ^ "Poisons Act 1964" (PDF). Archived from the original (PDF) on 2015-12-22. Retrieved 2015-12-13.
  11. ^ "Läkemedelsverkets författningssamling" (PDF) (in Swedish).
  12. ^ "H.R. 1254 (112th): Synthetic Drug Control Act of 2011". GovTrack. Retrieved 30 September 2015.
  13. ^ "Explore N-(2C-I)-Fentanyl | PiHKAL · info". isomerdesign.com.
[edit]
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