From Wikipedia, the free encyclopedia
Jump to: navigation, search
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 307.13 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.

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. 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. 2C-I's effective dosage range per milligram is approximately 10-fold less than mescaline. 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 usually occurs within two hours, and the effects of the drug typically last somewhere in the range of 4 to 12 hours (depending on the dose). The effects of the drug at small dosages (less than 12 mg) has been reported as more mental and less sensory than those of 2C-B. Users of 2C-I do, however, tend to report a physical stimulant effect, often quite strong and clean.[8] The effects of the drug at larger dosages (12-30+ mg) are often described as combining psychedelic or hallucinogenic effects typical of drugs such as LSD with the empathogenic or entactogenic effects of drugs such as MDMA (ecstasy). Although unpleasant physical side-effects such as muscle tension, nausea, and vomiting have been reported, their incidence with the use of 2C-I appears to be less common than with some closely related phenethylamines such as 2C-T-2 and 2C-T-7. Some physical effects include dilated pupils, high energy, and muscle relaxation. Users report feeling light and sometimes giddy or excited during the first two hours. Users also report that heavy music, usually electronic, and other auditory stimulation is enjoyable.


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.


2c-i has been reported by users to degrade with elevated temperatures. It's degraded form has been purported to inhibit production of mucus from the mucus membranes. This can cause difficulty swallowing/breathing by pulling a vacuum on the inner ear.

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.


Controlled substance.[9]


Controlled substance.[9]


Controlled substance.[9]


Controlled substance.[9]


Controlled substance.[9]


Controlled substance.[9]


Controlled substance.[9]


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]


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". 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. ^ TheSite.org, 2009
  9. ^ a b c d e f g h i Erowid.org, Legal Status of 2C-I
  10. ^ http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf

External links[edit]