2C-I
Template:Cs1 config Template:Infobox drug
2C-I, also known as 4-iodo-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.<ref name="PiHKAL">Template:CitePiHKAL https://erowid.org/library/books_online/pihkal/pihkal033.shtml</ref><ref name="Anilanmert_2018" /><ref name="Dean_2013">Template:Cite journal</ref><ref name="Bosak_2013">Template:Cite journal</ref> It is taken orally.<ref name="PiHKAL" /><ref name="Dean_2013" />
2C-I was first synthesized and described by Alexander Shulgin in 1977<ref name="Shulgin_1978" /><ref name="Braun_1977" /> and was described in further detail in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).<ref name="PiHKAL" /> 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.<ref>Template:Cite web</ref><ref name="weiss">Weiss, Piper (September 20, 2012). 2C-I or 'Smiles': The New Killer Drug Every Parent Should Know About. Yahoo! News</ref><ref name="Mackin_2012">Template:Cite web WISH-TV</ref>
Use and effects
According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved), 2C-I has a dose range of 14 to 22Template:Nbspmg orally and a duration of 6 to 10Template:Nbsphours.<ref name="PiHKAL" /><ref name="Dean_2013" /> Its onset is within 40Template:Nbspminutes and peak effects occur after about 2Template:Nbsphours.<ref name="PiHKAL" /> In addition to oral administration, 2C-I may also be insufflated.<ref name="Reuters2011">Reuters (March 20, 2011). Synthetic drug, subject of proposed bans, kill teen.</ref> 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.<ref name="PiHKAL" /> The sensual effects of 2C-I were described as different from and possibly less than those of 2C-B.<ref name="PiHKAL" />
Interactions
2C-I is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.<ref name="Dean_2013">Template:Cite journal</ref><ref name="Theobald_2007">Template:Cite journal</ref> Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-I.<ref name="Dean_2013" /><ref name="Theobald_2007" /><ref name="Halman_2024">Template:Cite journal</ref> This may result in overdose and serious toxicity.<ref name="Halman_2024" /><ref name="Dean_2013" />
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 107–970 (Ki) 4,900 (Template:Abbrlink) 102% (Template:Abbrlink) |
| 5-HT1B | 56 |
| 5-HT1D | 40 |
| 5-HT1E | 131 |
| 5-HT1F | Template:Abbr |
| 5-HT2A | 3.5–9.3 (Ki) 1.48–513 (Template:Abbr) 17–93% (Template:Abbr) |
| 5-HT2B | 9.3 (Ki) 19.1–150 (Template:Abbr) 70–101% (Template:Abbr) |
| 5-HT2C | 9.3–40 (Ki) 0.46–537 (Template:Abbr) 44–107% (Template:Abbr) |
| 5-HT3 | >10,000 |
| 5-HT4 | Template:Abbr |
| 5-HT5A | >10,000 |
| 5-HT6 | Template:Abbr |
| 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 | Template:Abbr |
| 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 | Template:Abbr |
| σ1 | >10,000 |
| σ2 | 5,470 |
| MOR | 2,522 |
| DOR | Template:Abbr |
| KOR | >10,000 |
| Template:Abbrlink | 3,300 (Ki) (mouse) 120 (Ki) (rat) 2,400 (Template:Abbr) (mouse) 190 (Template:Abbr) (rat) >10,000 (Template:Abbr) (human) 51% (Template:Abbr) (mouse) 50% (Template:Abbr) (rat) |
| Template:Abbrlink | 950–4,900 (Ki) 5,600–13,000 (Template:Abbrlink) Template:Abbr (Template:Abbr) |
| Template:Abbrlink | 15,000 (Ki) 22,000 (Template:Abbr) Template:Abbr (Template:Abbr) |
| Template:Abbrlink | >30,000 (Ki) 126,000 (Template:Abbr) Template:Abbr (Template:Abbr) |
| Template:Abbrlink | 125,000 (Template:Abbr) |
| Template:Abbrlink | 55,000 (Template:Abbr) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: <ref name="PDSPKiDatabase">Template:Cite web</ref><ref name="Rickli_2015">Template:Cite journal</ref><ref name="Eshleman_2014">Template:Cite journal</ref><ref name="Ettrup_2011">Template:Cite journal</ref><ref name="Rudin_2022">Template:Cite journal</ref><ref name="Pottie_2020">Template:Cite journal</ref> <ref name="Wallach_2023">Template:Cite journal</ref><ref name="AcunaCastillo_2002">Template:Cite journal</ref><ref name="Moya_2007">Template:Cite journal</ref><ref name="Flanagan_2021" /><ref name="Wagmann_2019">Template:Cite journal</ref><ref name="Simmler_2016">Template:Cite journal</ref> | |
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.<ref name="Eshleman_2014" /><ref name="Rickli_2015" />
2C-I is a highly potent anti-inflammatory drug similarly to various other serotonergic psychedelics.<ref name="Flanagan_2021">Template:Cite journal</ref> However, 2C-I showed the highest anti-inflammatory potency of any other assessed drug in a large series in one study.<ref name="Flanagan_2021" /> It was more potent than (R)-DOI in terms of anti-inflammatory activity.<ref name="Flanagan_2021" />
Chemistry
Synthesis
The chemical synthesis of 2C-I has been described.<ref name="PiHKAL" /><ref name="Shulgin_2011">Template:Cite book</ref>
Analogues
Analogues of 2C-I include 2C-H (2,5-DMPEA), 2C-B, 2C-C, DOI, and 25I-NBOMe, among others.<ref name="PiHKAL" /><ref name="Trachsel_2013">Template:Cite book</ref><ref name="Anilanmert_2018">Template:Cite book</ref>
History
2C-I was first described in the scientific literature by Alexander Shulgin and colleagues in 1977.<ref name="Shulgin_1978">Template:Cite book</ref><ref name="Braun_1977">Template:Cite journal</ref> Its properties and effects in humans were described by Shulgin in 1978.<ref name="Shulgin_1978" /> The drug was subsequently described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).<ref name="PiHKAL" /> In the early 2000s, 2C-I was sold in Dutch smart shops as a recreational drug after the related drug 2C-B was banned.<ref name="de_Boer_1999">Template:Cite journal</ref>
Society and culture
Legal status
Australia
2C-I is a schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).<ref name="Poisons Standard">Poisons Standard October 2015</ref> 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".<ref>Template:Cite web</ref>
Canada
As of October 31, 2016, 2C-I is a controlled substance (Schedule III) in Canada.<ref>Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)</ref>
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.<ref name="erowid-law">Template:Cite web</ref>
Finland
Illegal: scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs".<ref>Template:Cite web</ref>
Sweden
Sveriges riksdag added 2C-I to schedule I ("substances, plant materials and fungi which normally do not have medical use") as a narcotic on March 16, 2004, published by the Medical Products Agency in their regulation LVFS 2004:3.<ref>Template:Cite web</ref>
United Kingdom
In the United Kingdom, 2C-I is controlled as a Class A substance.<ref name="erowid-law" />
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.<ref name="erowid-law" /> 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.<ref>Template:Cite web</ref>
See also
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
Template:Psychedelics Template:Serotonin receptor modulators Template:TAAR modulators Template:Phenethylamines