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2C-I animation.gif
IUPAC name
69587-11-7 N
ChEMBL ChEMBL338297 YesY
ChemSpider 8442670 YesY
Jmol interactive 3D Image
PubChem 10267191
UNII S35362848V N
Molar mass 307.13 g/mol
Melting point 246 °C (475 °F; 519 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

2C-I (2,5-dimethoxy-4-iodophenethylamine is a psychedelic phenethylamine of the 2C family.[1] It was first synthesized by Alexander Shulgin and described in his 1991 book PiHKAL: A Chemical Love Story. The drug is used recreationally for its psychedelic and entactogenic effects and is sometimes confused for the analog 25I-NBOMe, nicknamed "Smiles," in the media.[2][3][4]

Recreational use[edit]

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

2C-I is often misrepresented as mescaline in US street sale and both chemicals are members of the psychedelic phenethylamine class of drugs, except 2C-I is an analog of mescaline in the 2C-x series.[citation needed] According to the US government's Drug Enforcement Administration, 2C-I is taken orally or snorted in a powder form.[6]


The incidence of unpleasant side-effects is less commonly reported than with other closely related substituted phenethylamines such as 2C-T-2 and 2C-T-7 which also act as monoamine oxidase inhibitors and may have other action on amine re-uptake.[citation needed] Visual effects of 2C-I exposure have been described by many users as iterating fractals, along with a more generalized shift in perception and/or cognition.[7]

Drug prohibition laws[edit]

European Union[edit]

In December 2003, the European Council issued a binding order compelling all EU member states to ban 2C-I within three months.[8]


Controlled substance.[8]


Controlled substance.[8]


Controlled substance.[8]


Controlled substance.[8]


Controlled substance.[8]


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 in their regulation LVFS 2004:3 listed as 4-jodo-2,5-dimetoxifenetylamin (2C-I).[9]

United Kingdom[edit]

Controlled as a Class A substance.[8]


In March of 2011 a bill was introduced that would classify 2C-I and many other substances as a schedule I substance. The bill passed the House of Representatives but was not passed by the Senate.[10] 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.[8]

See also[edit]


External links[edit]