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2C-I-3d-sticks.png 2C-I animation.gif
CAS number 69587-11-7 N
PubChem 10267191
ChemSpider 8442670 YesY
Jmol-3D images Image 1
Molecular formula C10H14INO2
Molar mass Script error g mol−1
Melting point 246 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

2C-I or 2,5-dimethoxy-4-iodophenethylamine is a psychedelic phenethylamine of the 2C family.[1] It was first synthesized by Alexander Shulgin. It was described in Shulgin’s 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 1–8 mg.[medical citation needed]

Recreational use

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. During the same period, 2C-I also became available in powder form from several online vendors of research chemicals in the United States, Asia, and Western Europe.

It is often misrepresented as mescaline in US street sale of singular dosages, as it shares some level of similarity in psychological effect. Both chemicals are members of the psychedelic phenethylamine class of drugs, except 2C-I is an analog of mescaline in the 2C-x series. A major difference between the research chemicals in the 2C-x series and mescaline is a much greater potency by weight and thus also a steeper dose-response in the newer synthetic drugs.[citation needed] 2C-I's effective dosage range per milligram is approximately 10-fold less than mescaline.[medical citation needed] This means that a small carrier material, such as a small candy or pressed pill, is suitable for 2C-I. That type of small carrier material has an insufficiently small holding capacity to contain a large enough quantity of mescaline to produce a substantial psychoactive effect.

According to the United States Drug Enforcement Agency 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 to two hours when taken orally, and 10–20 minutes when insufflated; lasting between 4 to 12 hours (depending on the dose) though some users have reported a duration of 16–18 hours.[medical citation needed] A shorter duration is typical for insufflated doses. The effects at small dosages (less than 12 mg) has been reported as more mental and less sensory than those of 2C-B. Users often report strong physical stimulation.[8] Unpleasant physical side-effects including muscle tension, hypertensive crisis, overstimulation, nausea, vomiting, seizures have been reported. The incidence of unpleasant side effects is less commonly reported than with other closely related substituited phenethylamines such as 2C-T-2 and 2C-T-7 which also act as monoamine oxidase inhibitors and may have other action on amine reuptake. 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.[9]


Oral Dosage
ED50 2–5 mg

5–15 mg


10–25 mg


20–30 mg




4-8 Hours

Insufflated (Snorted) Dosage
ED50 0.5–2 mg
Moderate 5–10 mg
Strong 10+ mg

4-8 Hours

The lethal dosage is unknown.

Tolerance and Degradation

2C-I has been noted by several users to decrease in visual or psychedellic effects with repeated administration, and to increase in symptoms of hypertensive crisis. 2C-I is also known to degrade in heat, and though the degradation products are yet unclassified user reports of degraded 2C-I allege the absence of psychedellic affect. The degraded form has also been reported by several users to have an opposite affect on saliva production, inhibiting it almost entirely in some instances. This factor has been noted as particularly uncomfortable or dangerous, as the action of swallowing without a fluid buffer causes a vacuum to pull on the inner ear.[10]

Drug prohibition laws

European Union

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


Controlled substance.[11]


Controlled substance.[11]


Controlled substance.[11]


Controlled substance.[11]


Controlled substance.[11]


Controlled substance.[11]


Controlled substance.[11]


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).[12]

United Kingdom

Controlled as a Class A substance.[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.[11]

See also


  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". Journal of Analytical Toxicology 23 (3): 227–228. PMID 10369336. doi:10.1093/jat/23.3.227. 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. TheSite.org, 2009
  9. https://www.erowid.org/chemicals/2ci/
  10. http://www.erowid.org/ask/ask.php?ID=3071
  11. 11.0 11.1 11.2 11.3 11.4 11.5 11.6 11.7 11.8 Erowid.org, Legal Status of 2C-I
  12. http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf

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