white → green3 → black3
2C-I
2,5-Dimethoxy-4-iodophenethylamine
Smiles
2C-I is a synthetic phenethylamine psychedelic and member of the 2C-x family, a group of compounds derived through systematic modifications of mescaline. Alexander Shulgin synthesized it in 1976 and included it in PiHKAL, published in 1991.1 Often compared to 2C-B though less widely used, 2C-I gained popularity as a recreational psychedelic in the late 1990s. It is sometimes confused with the more dangerous analog 25I-NBOMe.2
Dosage & Duration
Dosage
Threshold~2 mg
Light2-10 mg
Moderate10-20 mg
Strong20-30 mg
Heavy30+ mg
Effects respond steeply to small dose changes; a difference of as little as 2 mg can noticeably alter intensity, so gradual titration is advised. Doses above 35 mg can be unpleasantly strong even for experienced users.
Duration
Onset20-90 minutes
Come Up30-60 minutes
Peak3-5 hours
Offset1-2 hours
After Effects4-12 hours
Total6-10 hours
Subjective Effects
Effects vary widely by individual, dose, and context.
Physical
Cognitive
The head space of 2C-I is described by many as one which is relatively normal in its thought processes even at moderate to high dosages. It is often said to lack insight when compared to that of 2C-E, 2C-B and LSD.
Visual
Distortions
Geometry
The visual geometry of 2C-I can be described as more similar in appearance to that of LSD or 2C-B than that of 2C-E, psilocin, or ayahuasca although it is much more bland and less detailed. They can be comprehensively described as unstructured in their organization, algorithmic in geometric style, intricate in complexity, large in size, fast and smooth in motion, colourful in scheme, glossy in colour, both soft and sharp in their edges as well as equally rounded and angular in their corners. They seem high in algorithmic visuals such as fractals and at higher dosages are significantly more likely to result in states of Level 7A visual geometry over Level 7B.
Hallucinatory States
Like LSD, while 2C-I is capable of producing a full range of low and high level hallucinatory states, this is extremely rare and inconsistent at higher levels but common at lower levels.
Auditory
Pharmacology
Pharmacodynamics
2C-I has assay-dependent signaling at human serotonin receptors. In recombinant-cell assays it was a full agonist at 5-HT2A and 5-HT2C receptors in the inositol-phosphate pathway, but an antagonist at 5-HT2A in an arachidonic-acid-release assay. It also had moderate affinity but very low functional potency at the serotonin transporter. These results support a serotonergic mechanism while cautioning against describing 2C-I with one unqualified efficacy label. [S1]
Pharmacokinetics
Experiments with recombinant human enzymes identified MAO-A and MAO-B as the major enzymes catalyzing 2C-I deamination to its corresponding aldehyde. [S2] In rats, 2C-I also underwent O-demethylation at both methoxy positions, N-acetylation, and deamination followed by oxidation or reduction; the parent compound and many metabolites were partly excreted as conjugates. [S3] The rat study did not have authentic human urine, so this metabolite pattern must not be presented as a confirmed human profile. [S3]
Metabolitesnone documented yet
Dangerous
Highest riskThese combinations are considered extremely harmful and should always be avoided. Reactions to these drugs taken in combination are highly unpredictable and have a potential to cause death.
Unsafe
AvoidThere is considerable risk of physical harm when taking these combinations, they should be avoided where possible.
Caution
Use cautionThese combinations are not usually physically harmful, but may produce undesirable effects, such as physical discomfort or overstimulation. Extreme use may cause physical health issues. Synergistic effects may be unpredictable. Care should be taken when choosing to use this combination.
Tolerance
Full Tolerance
Tolerance to the effects of 2C-I develops almost immediately after ingestion. Using 2C-I on consecutive days will result in a noticeably diminished experience on the second day.
Baseline Reset
7-10 days without further consumption. Some sources suggest that spacing use 5-7 days apart results in minimal tolerance effects.
Half Tolerance
3-5 days
Cross Tolerance
Serotonergic psychedelics3
Harm Potential
Addiction & Dependence
Psychological
Extremely Low2C-I is not considered habit-forming and the desire to use it may actually decrease with repeated use, consistent with classical psychedelics. Some individuals may use it more frequently than intended, but psychological dependence is unlikely.
Physical
Extremely Low2C-I is not physically addicting and withdrawal effects following discontinuation have not been reported.
Psychosis Risk
As with psychedelics generally, 2C-I may trigger latent psychological and mental problems in susceptible individuals. Those with a family history of schizophrenia or early onset mental illness should exercise extreme caution. Acute psychological effects such as disorientation, confusion, anxiety, and fear of death may occur during intoxication.
History & Culture
Discovery and Synthesis
2C-I was first synthesized and investigated for human activity by Alexander Shulgin in the mid-to-late 1970s. The compound was initially described in scientific literature in 19774, with its properties and effects in humans documented the following year. Shulgin later…
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Legality
International
1961 Single Convention: 2C-I is not individually scheduled.
1971 Convention on Psychotropic Substances: Schedule I.
1988 Convention: 2C-I is not listed in precursor Tables I or II.
By Country
United StatesIllegalSchedule I hallucinogen
21 CFR § 1308.11(d)14
Current official national law expressly controls 2C-I in United States; unauthorized possession, supply, or manufacture is prohibited.
AustriaIllegal (SMG)Citation needed
Controlled under the Suchtmittelgesetz (Narcotics Act). Possession, production, and sale are prohibited.
BrazilIllegalCitation needed
Possession, production, and sale prohibited under Portaria SVS/MS nº 344. Controlled as of February 18, 2014.
ChinaCategory I Psychotropic SubstanceCitation needed
Illegal to sell, buy, import, export, and manufacture as of September 2010.
DenmarkControlledCitation needed
Classified as a controlled substance since May 2002.
FinlandIllegalCitation needed
Scheduled under the government decree on substances, preparations, and plants considered to be narcotic drugs.11
GermanyIllegalAnlage I controlled substance
Betäubungsmittelgesetz, Anlage I12
Current official national law expressly controls 2C-I in Germany; unauthorized possession, supply, or manufacture is prohibited.
IrelandSchedule 1Citation needed
Controlled as a Schedule 1 substance, prohibiting possession and distribution.
ItalyTabella ICitation needed
Added to Tabella 1 (list of prohibited plants and substances) by Ministry of Health statement on January 11, 2005.
LatviaSchedule ICitation needed
Classified as a Schedule I controlled substance.
New ZealandSchedule 3 / Class CCitation needed
Controlled under the catch-all analogues provision in Schedule 3 / Class C of national drug laws.
PortugalControlledCitation needed
Legislation enacted in January 2005 to control 2C-I alongside 2C-T-2, 2C-T-7, and TMA-2.
SwitzerlandControlled (Verzeichnis D)Citation needed
Listed in Anhang D of the Betäubungsmittelverzeichnisverordnung (DetMV) since December 12, 1996. Possession is illegal.
United KingdomIllegalClass A · Schedule 1
Misuse of Drugs Act 1971; Misuse of Drugs Regulations 200113
Current official national law expressly controls 2C-I in United Kingdom; unauthorized possession, supply, or manufacture is prohibited.
AustraliaSchedule 9Citation needed
Prohibited substance under the Poisons Standard. The National Drugs and Poisons Schedule Committee formally added 2C-I to Schedule 9 (the most restrictive category) in 2005.
BelgiumIllegalCitation needed
Added to the list of illegal psychotropic substances on November 8, 2004.
CanadaIllegalSchedule III controlled substance
Controlled Drugs and Substances Act, Schedule III10
Current official national law expressly controls 2C-I in Canada; unauthorized possession, supply, or manufacture is prohibited.
Czech RepublicControlledCitation needed
Added to controlled substance lists in early 2011 alongside BZP, synthetic cannabinoids, and various cathinone derivatives.
EstoniaSchedule ICitation needed
Added to Schedule I in February 2011 alongside various synthetic cathinones and cannabinoids.
FranceControlledCitation needed
Added to the list of controlled substances in August 2004 as a synthetic analogue of mescaline.
GreeceControlledCitation needed
Illegal to possess under Table A of Law 1729/87.
IsraelControlledCitation needed
Added to the list of controlled substances in December 2007, making purchase, sale, and possession illegal.
JapanDesignated Substance (Shitei-Yakubutsu)Citation needed
Controlled under the Pharmaceutical Affairs Law, making possession and sale illegal.
NetherlandsControlledCitation needed
Classified as a controlled substance under national drug legislation.
PolandControlledCitation needed
Classified as a controlled substance under national drug legislation.
SwedenSchedule I (Narcotic)Citation needed
Added to Schedule I by Sveriges riksdag on March 16, 2004, published in Medical Products Agency regulation LVFS 2004:3. Classified as a substance normally without medical use.
TurkeyIllegalCitation needed
Classified as a drug. Possession, production, supply, and import are prohibited.
References
Source Pages
Citations
- Be Vang Dean, Samuel J. Stellpflug, Aaron M. Burnett, & Kristin M. Engebretsen. (June 2013). 2C or not 2C: phenethylamine designer drug review. Journal of Medical Toxicology, 9(2), 172–178. https://doi.org/10.1007/s13181-013-0295-x12
- Nikolaou P, Papoutsis I, Stefanidou M, Spiliopoulou C, & Athanaselis S. (2015). 2C-I-NBOMe, an "N-bomb" that kills with "Smiles". Toxicological and legislative aspects. Drug and Chemical Toxicology, 38(1), 113-119. https://doi.org/10.3109/01480545.2014.91188212
- Adam L. Halberstadt. (January 2015). Recent advances in the neuropsychopharmacology of serotonergic hallucinogens. Behavioural Brain Research, 277, 99-120. https://doi.org/10.1016/j.bbr.2014.07.0161
- Synthesis and body distribution of several iodine-131 labeled centrally acting drugs. Journal of Medicinal Chemistry, 20(12), 1543–1546 (December 1977). https://doi.org/10.1021/jm00222a00112
- Alexander Shulgin, & Ann Shulgin. (1991). PiHKAL: A Chemical Love Story. Transform Press. https://erowid.org/library/books_online/pihkal/pihkal033.shtml123
- U.S. Drug Enforcement Administration. (July 22, 2004). DEA Announces Arrests of Website Operators Selling Illegal Designer Drugs. U.S. Department of Justice, Drug Enforcement Administration. https://web.archive.org/web/20091002091419/http://www.usdoj.gov:80/dea/pubs/pressrel/pr072204.html1
- Hill SL, & Thomas SH. (2013). 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25I-NBOMe): clinical case with unique confirmatory testing. Clinical Toxicology. https://pmc.ncbi.nlm.nih.gov/articles/PMC3951642/1
- 25I-NBOMe (2C-I-NBOMe): Fatalities / Deaths. (n.d.). http://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml1
- Dangerous synthetic drug making its way across the country.. (October 9, 2012). http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country1
- Controlled Drugs and Substances Act, Schedule III. laws-lois.justice.gc.ca (n.d.). https://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-17.html1
- Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista | 543/2008 | Lainsäädäntö | Finlex. (n.d.). https://finlex.fi/fi/lainsaadanto/2008/5431
- Gesetz über den Verkehr mit Betäubungsmitteln: Anlage I. (2019). https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html1
- Misuse of Drugs Act 1971; Misuse of Drugs Regulations 2001. gov.uk (n.d.). https://www.gov.uk/government/publications/controlled-drugs-list--2/list-of-most-commonly-encountered-drugs-currently-controlled-under-the-misuse-of-drugs-legislation1
- 21 CFR § 1308.11(d). ecfr.gov (n.d.). https://www.ecfr.gov/current/title-21/chapter-II/part-1308/section-1308.111
- Reviewed & approved
Reviewed, edited, and approved by subject-matter expert Lyrea.
Automated synthesisInformation aggregated and synthesized using an autonomous workflow built by Josie Kins.
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