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Summary sheet: 2C-I
Chemical Nomenclature
Common names 2C-I
Substitutive name 2,5-Dimethoxy-4-iodophenethylamine
Systematic name 2-(4-Iodo-2,5-dimethoxyphenyl)ethan-1-amine
Class Membership
Psychoactive class Psychedelic
Chemical class Phenethylamine
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.

Threshold 2 mg
Light 5 - 10 mg
Common 10 - 20 mg
Strong 20 - 30 mg
Heavy 30 mg +
Total 6 - 10 hours
Onset 15 - 45 minutes
Come up 45 - 90 minutes
Peak 3 - 5 hours
Offset 2 - 3 hours
After effects 6 - 24 hours

DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.


2,5-Dimethoxy-4-iodophenethylamine (also known as 2C-I and "Smiles") is a psychedelic substance of the phenethylamine class. It is a member of the 2C-x family of psychedelic phenethylamines, all of which were derived from the systematic modification of the mescaline molecule.[1]

2C-I was first synthesized and investigated for human activity by Alexander Shulgin in 1976[2] and later described in his 1991 book PiHKAL ("Phenethylamines I Have Known and Loved"). Its PiHKAL entry notes it for being "very colorful and active" but without "feelings of insight, revelation, or progress toward the true meaning of the universe."[1] It first briefly gained some popularity in the late 1990s and early 2000s, where it was sold in several smart shops as a replacement for 2C-B following its scheduling in 1995.[3] It also has a history of being sold online as a research chemical before becoming scheduled.

2C-I is typically used recreationally for its psychedelic as well as moderate stimulating and entactogenic effects. It has been explored as a potential stimulant nootropic in the 1-8mg dosage range.[citation needed]

Little data exists about the pharmacological properties, metabolism, and toxicity of 2C-I, and it has a limited history of human use. 2C-I is sometimes confused for the analog 25I-NBOMe (an abbreviated form of 2C-I-NBOMe). It is highly advised to use harm reduction practices if using this substance.



This chemistry section is incomplete.

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Generic structure of a phenethylamine molecule

2C-I, or 2,5-dimethoxy-4-iodophenethylamine, is a substituted phenethylamine comprising a phenyl ring bound to an amino (NH2) group through an ethyl chain. 2C-I contains methoxy functional groups CH3O- attached to carbons R2 and R5 as well as an iodine atom attached to carbon R4 of the phenyl ring. 2C-I belongs to the 2C family of phenethylamines which contain methoxy groups on the 2 and 5 positions of the benzene ring.


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This pharmacology section is incomplete.

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Further information: Serotonergic psychedelic

2C-I is a psychedelic phenethylamine of the 2C-x family. 2C-I is taken orally in tablet or capsule forms or snorted in its powder form. It has also been found impregnated on small squares of blotter paper for oral administration, which is a technique often seen for the distribution and abuse of LSD. 2C-I primarily causes stimulant and hallucinogenic effects, including increased visual, auditory, and tactile sensations. Moderate doses can cause full hallucinations and can also produce a euphoric high.

2C-I's psychedelic effects are believed to come from its efficacy at the 5-HT2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience remains the subject of ongoing scientific investigation.

Subjective effects

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

Physical effects

Visual effects

Cognitive effects

Multi-sensory effects

Transpersonal effects

Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include:

Additional experience reports can be found here:

Toxicity and harm potential


This toxicity and harm potential section is a stub.

As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it.
Note: Always conduct independent research and use harm reduction practices if using this substance.

The toxicity and long-term health effects of recreational 2C-I use do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because 2C-I is a research chemical with very little history of human usage.

Anecdotal reports from those who have tried 2C-I suggests that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

It is strongly recommended that one use harm reduction practices, such as volumetric dosing, when using this substance so as to ensure the accurate administration of the intended dose.

Tolerance and addiction potential

Although no formal studies have been conducted, it is not unreasonable to assume that as is the case with psychedelics in general, 2C-I is not habit-forming and that the desire to use it can actually decrease with use.

Tolerance to the effects of 2C-I is built almost immediately after ingestion. After that, it takes about 3-5 days for the tolerance to be reduced to half and 7-10 days to be back at baseline (in the absence of further consumption). 2C-I presents cross-tolerance with all psychedelics, meaning that after the consumption of 2C-I all psychedelics will have a reduced effect.

Dangerous interactions

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

Legal status

In November 2003, the European Council decided that 2C-I shall be subjected by the Member States to control measures and criminal penalties within three months.[5]

  • Austria: 2C-I is illegal to possess, produce and sell under the SMG. (Suchtmittelgesetz Österreich)[citation needed]
  • Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[6]
  • Canada: 2C-I is a schedule III controlled substance in Canada.[7]
  • Denmark: 2C-I is a controlled substance in Denmark.[8]
  • Germany: 2C-I is controlled under Anlage I BtMG[9] (Narcotics Act, Schedule I) as of October 10, 1999.[10] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[11]
  • Greece: 2C-I is a controlled substance in Greece.[8]
  • Ireland: 2C-I is a controlled substance in Ireland.[8]
  • Italy: 2C-I is a controlled substance in Italy.[8]
  • Latvia: 2C-I is a Schedule I controlled substance Latvia.[12]
  • The Netherlands: 2C-I is a controlled substance in the Netherlands.[8]
  • Poland: 2C-I is a controlled substance in Poland.[8]
  • Sweden: Sveriges riksdag added 2C-I to Schedule I ("substances, plant materials and fungi which normally do not have medical use") as a narcotic in Sweden as of March 16, 2004.[13]
  • Switzerland: 2C-I is a controlled substance specifically named under Verzeichnis D.[14]
  • Turkey: 2C-I is classed as a drug and is illegal to possess, produce, supply, or import.[15]
  • United Kingdom: 2C-I is a Class A drug in the United Kingdom as a result of the phenethylamine catch-all clause.[16]
  • United States: As of July 9, 2012, 2C-I is a Schedule I substance in the U.S. under the Synthetic Drug Abuse Prevention Act of 2012, making possession, distribution and manufacture illegal.[8]

See also

External links



  1. 1.0 1.1 Alexander Shulgin; Ann Shulgin (1991). "#33. 2C-I". PiHKAL: A Chemical Love Story. United States: Transform Press. ISBN 0963009605. OCLC 1166889264. 
  2. Alexander Shulgin. Pharmacology Notes I (The Shulgin Lab Books) (PDF). Erowid. p. 177. 
  3. Eric Johnson (March 19, 2011). Ellen Wulfhorst, ed. "Synthetic drug, subject of proposed bans, kill teen". Reuters. Retrieved October 11, 2020. 
  4. Talaie, H.; Panahandeh, R.; Fayaznouri, M. R.; Asadi, Z.; Abdollahi, M. (2009). "Dose-independent occurrence of seizure with tramadol". Journal of Medical Toxicology. 5 (2): 63–67. doi:10.1007/BF03161089. ISSN 1556-9039. 
  5. "COUNCIL DECISION 2003/847/JHA". Official Journal of the European Union. Office for Official Publications of the European Communites (published December 6, 2003). November 27, 2003. pp. 64–65. OCLC 52224955. L 321. 
  6. "RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016" (in Portuguese). Agência Nacional de Vigilância Sanitária (ANVISA) [Brazilian Health Regulatory Agency (ANVISA)]. December 5, 2016. 
  7. "Schedule III". Controlled Drugs and Substances Act (CDSA). Isomer Design. Retrieved October 10, 2020. 
  8. 8.0 8.1 8.2 8.3 8.4 8.5 8.6 "2C-I: Legal Status". Erowid. Retrieved March 13, 2014. 
  9. "Gesetz über den Verkehr mit Betäubungsmitteln: Anlage I" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019. 
  10. "Dreizehnte Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (PDF). Bundesgesetzblatt Jahrgang 1999 Teil I Nr. 46 (in German). Bundesanzeiger Verlag [Federal Gazette] (published September 30, 1999). September 24, 1999. p. 1935. eISSN 0344-7634. 
  11. "Gesetz über den Verkehr mit Betäubungsmitteln: § 29" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019. 
  12. "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). VSIA Latvijas Vēstnesis. November 10, 2005. Retrieved January 1, 2020. 
  13. "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997:12) om förteckningar över narkotika" (PDF) (in Swedish). Läkemedelsverket [Medical Products Agency ] (published March 16, 2004). February 24, 2004. ISSN 1101-5225. LVFS 2004:3. Archived from the original (PDF) on June 13, 2018. 
  14. "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020. 
  15. Bakanlar Kurulu Kararı Karar Sayısı : 2013/4827 | https://free-ankara.org/wp-content/uploads/2017/09/BKK_2013_4827_28688.pdf
  16. "Schedule 2: Part I: Class A Drugs". "Misuse of Drugs Act 1971". UK Government. Retrieved August 20, 2020.