From Wikipedia, the free encyclopedia
Jump to: navigation, search
2C-I animation.gif
IUPAC name
CAS number 69587-11-7 N
ChEMBL ChEMBL338297 YesY
ChemSpider 8442670 YesY
Jmol-3D images Image
PubChem 10267191
Molar mass 307.13 g·mol−1
Melting point 246 °C (475 °F; 519 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/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[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 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 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] A shorter duration is typical for insufflated doses. The effects at small dosages (less than 12 mg) have 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, over-stimulation, nausea, vomiting, and seizures have been reported. 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.[9]


Oral Dosage[10]
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[edit]

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. 2C-I is also known to degrade in heat, and though the degradation products are as of yet unclassified, user reports of degraded 2C-I allege the absence of psychedelic affect. The degraded form has also been reported by several users to have an opposite effect 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.[11]

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.[12]


Controlled substance.[12]


Controlled substance.[12]


Controlled substance.[12]


Controlled substance.[12]


Controlled substance.[12]


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).[13]

United Kingdom[edit]

Controlled as a Class A substance.[12]


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.[12]

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. ^ https://www.erowid.org/chemicals/2ci/
  10. ^ "2C-I Dosage". Erowid. Feb 21, 2003. Retrieved 3 November 2014. 
  11. ^ http://www.erowid.org/ask/ask.php?ID=3071
  12. ^ a b c d e f g h Erowid.org, Legal Status of 2C-I
  13. ^ http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf

External links[edit]