2C-I, also known as 4-iodo-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It is taken orally.
2C-I was first synthesized and described by Alexander Shulgin in 1977 and was described in further detail in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). The drug is used recreationally. 2C-I is sometimes confused with other related psychedelic drugs such as 25I-NBOMe (NBOMe-2C-I), nicknamed "Smiles" and "N-bomb" in the media. WISH-TV
Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-I's dose as 14 to 22mg orally and its duration as 6 to 10hours. Its onset is within 40minutes and peak effects occur after about 2hours. 2C-I is reported to be administered orally or via insufflation, as documented by the U.S. Drug Enforcement Administration. The effects of 2C-I have been reported to include color enhancement, psychedelic visuals, emotional enhancement, limited insights, increased energy, enhanced conversation and honesty, improved mood, and sensual immersion. The sensual effects of 2C-I were described as different from and possibly less than those of 2C-B.
Interactions
2C-I is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B. Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-I. This may result in overdose and serious toxicity.
Pharmacology Pharmacodynamics + Target Affinity (Ki, nM) 5-HT1A 107–970 (Ki)4,900 ()102% () 5-HT1B 56 5-HT1D 40 5-HT1E 131 5-HT1F 5-HT2A 3.5–9.3 (Ki)1.48–513 ()17–93% () 5-HT2B 9.3 (Ki)19.1–150 ()70–101% () 5-HT2C 9.3–40 (Ki)0.46–537 ()44–107% () 5-HT3 >10,000 5-HT4 5-HT5A >10,000 5-HT6 5-HT7 1,316 α1A 5,100–>10,000 α1B >10,000 α1D >10,000 α2A 70–305 α2B 608 α2C 315 β1 4,512 β2 >10,000 β3 D1 13,000 D2 1,013–2,700 D3 989–5,000 D4 2,788 D5 >10,000 H1 6,100 H2 >10,000 H3 >10,000 M1 >10,000 M2 1,429 M3 950 M4 1,129 M5 2,151 I1 σ1 >10,000 σ2 5,470 MOR 2,522 DOR KOR >10,000 3,300 (Ki) (mouse)120 (Ki) (rat)2,400 () (mouse)190 () (rat)>10,000 () (human)51% () (mouse)50% () (rat) 950–4,900 (Ki)5,600–13,000 () () 15,000 (Ki)22,000 () () >30,000 (Ki)126,000 () () 125,000 () 55,000 () Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:
2C-I acts as a serotonin receptor agonist. It produces psychedelic effects via serotonin 5-HT2A receptor activation.
It is inactive as a monoamine releasing agent and shows negligible activity as a monoamine reuptake inhibitor.
2C-I is a highly potent anti-inflammatory drug similarly to various other serotonergic psychedelics. However, 2C-I showed the highest anti-inflammatory potency of any other assessed drug in a large series in one study. It was more potent than (R)-DOI in terms of anti-inflammatory activity.
Chemistry Synthesis The chemical synthesis of 2C-I has been described.
Analogues Analogues of 2C-I include 2C-H (2,5-DMPEA), 2C-B, 2C-C, DOI, 4C-I, and 25I-NBOMe, among others.
History 2C-I was first described in the scientific literature by Alexander Shulgin and colleagues in 1977. Its properties and effects in humans were described by Shulgin in 1978. The drug was subsequently described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). In the early 2000s, 2C-I was sold in Dutch smart shops as a recreational drug after the related drug 2C-B was banned.
Society and culture Legal status
Australia 2C-I is a schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015). A schedule 9 drug is outlined in the Poisons Act 1964 as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO".
Canada As of October 31, 2016, 2C-I is a controlled substance (Schedule III) in Canada.
European Union In December 2003, the European Council issued a binding order compelling all European Union member states to ban 2C-I within three months.
Finland It is illegal in Finland, scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs".
Sweden In Sweden, the government classified 2C-I as a narcotic through SFS 2004:2, effective 1 March 2004. The Medical Products Agency subsequently listed it in List I of its narcotics schedules in LVFS 2004:3, which took effect on 15 March 2004.
United Kingdom In the United Kingdom,2C-I is controlled as a Class A substance.
United States 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. A previous bill, introduced in March 2011, that would have done the same passed the House of Representatives, but was not passed by the Senate.
See also 2C (psychedelics), such as 2C-B-FLY
References
External links 2C-I - Isomer Design 2C-I - PsychonautWiki 2C-I - Erowid 2C-I - PiHKAL - Erowid 2C-I - PiHKAL - Isomer Design 2C-I: An Obscure, But Powerful Research Chemical - TripSitter