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2C-I animation.gif
IUPAC name
69587-11-7 N
ChEMBL ChEMBL338297 YesY
ChemSpider 8442670 YesY
Jmol-3D images 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 isYesY/N?)
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] 2C-I is commonly sold in its hydrochloride salt form, which is a fluffy, sparkling-white powder, which can sometimes be pressed into a tablet form. 2C-I has been explored as a potential stimulant nootropic in doses between 1 mg and 8 mg.[medical citation needed]

Recreational use[edit]

In the early 2000s, 2C-I was sold in Dutch smart shops after the drug 2C-B was banned.[5] In April 2008, 2C-I was also banned in the Netherlands, along with three other 2C-x phenethylamines previously sold in Dutch smartshops for short periods of time.[citation needed] During the same period, 2C-I also became available in powder form from several online vendors of recreational drugs in the United States, Asia, and Western Europe.

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. According to the US government's Drug Enforcement Administration, 2C-I is taken orally or snorted in a powder form.[6] It can also be smoked or taken rectally.[7]


The onset of effects occurs between one and two hours when taken orally, and 10–20 minutes when insufflated; lasting between 4 and 12 hours (depending on the dose) though some users have reported a duration of 16–18 hours.[medical citation needed] Unpleasant physical side-effects including muscle tension, hypertensive crisis, over-stimulation, nausea, vomiting, and seizures have been reported.[medical citation needed] 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. 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.[8]


2C-I has been noted by several users to decrease in visual or psychedelic effects with repeated administration, and to increase in symptoms of hypertensive crisis.[medical citation needed]

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.[9]


Controlled substance.[9]


Controlled substance.[9]


Controlled substance.[9]


Controlled substance.[9]


Controlled substance.[9]


Controlled substance.[citation needed]


Controlled substance.[citation needed]


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).[10]

United Kingdom[edit]

Controlled as a Class A substance.[9]


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.[11] 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.[9]

See also[edit]


  1. ^ Erowid Online Books: PiHKAL
  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. WISH-TV
  5. ^ de Boer; et al. (May–June 1999). "More Data About the New Psychoactive Drug 2C-B" (PDF). Journal of Analytical Toxicology 23 (3): 227–228. doi:10.1093/jat/23.3.227. PMID 10369336. Retrieved 16 August 2012. 
  6. ^ Reuters (March 20, 2011). Synthetic drug, subject of proposed bans, kill teen.
  7. ^ European Monitoring Centre for Drugs and Drug Addiction (2004). Report on the risk assessment of 2C-1, 2C-T-2 and 2C-T-7 in the framework of the joint action on new synthetic drugs Office for Official Publications of the European Communities, p. 109. ISBN 9789291681815
  8. ^ https://www.erowid.org/chemicals/2ci/
  9. ^ a b c d e f g h Erowid.org, Legal Status of 2C-I
  10. ^ http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf
  11. ^ GovTrack https://www.govtrack.us/congress/bills/112/hr1254. Retrieved 30 September 2015.  Missing or empty |title= (help)

External links[edit]