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2C-I, also known as 2,5-dimethoxy-4-iodophenethylamine, is a phenethylamine of the 2C family with psychedelic effects.<ref>Template:Cite journal</ref> It was first synthesized by Alexander Shulgin, and is described in Shulgin's book PiHKAL (1991).
The substance is consumed as a recreational drug, and is circulated in the drug market in a powder form. 2C-I is sometimes confused with other related chemical substances such as 25I-NBOMe (2C-I-NBOMe), nicknamed "Smiles" and "N-bomb" in the media.<ref>{{#invoke:citation/CS1|citation |CitationClass=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="mackin2012">{{#invoke:citation/CS1|citation |CitationClass=web }} WISH-TV</ref>
UseEdit
In the early 2000s, 2C-I was sold in Dutch smart shops as a recreational drug after the drug 2C-B was banned.<ref name="Netherlands 2c-b emergence">Template:Cite journal</ref>
According to the US Drug Enforcement Administration, 2C-I is taken orally or snorted in a powder form.<ref name="reuters2011">Reuters (March 20, 2011). Synthetic drug, subject of proposed bans, kill teen.</ref>
InteractionsEdit
2C-I is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.<ref name="DeanStellpflugBurnett2013">Template:Cite journal</ref><ref name="TheobaldMaurer2007">Template:Cite journal</ref> Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-I.<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="HalmanKongSarris2024">Template:Cite journal</ref> This may result in overdose and serious toxicity.<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />
PharmacologyEdit
PharmacodynamicsEdit
| Target | Affinity (Ki, nM) | |
|---|---|---|
| 5-HT1A | 180–970 (Ki) 4,900 (Template:Abbrlink) 102% (Template:Abbrlink) | |
| 5-HT1B | Template:Abbr | |
| 5-HT1D | Template:Abbr | |
| 5-HT1E | Template:Abbr | |
| 5-HT1F | Template:Abbr | |
| 5-HT2A | 3.5–9.3 (Ki) 1.48–513 (Template:Abbr) 17–93% (Template:Abbr) | |
| 5-HT2B | 19.1–150 (Template:Abbr) 70–101% (Template:Abbr) | |
| 5-HT2C | 10–40 (Ki) 0.46–537 (Template:Abbr) 44–107% (Template:Abbr) | |
| 5-HT3 | Template:Abbr | |
| 5-HT4 | Template:Abbr | |
| 5-HT5A | Template:Abbr | |
| 5-HT6 | Template:Abbr | |
| 5-HT7 | Template:Abbr | |
| α1A | 5,100 | |
| α1B, α1D | Template:Abbr | |
| α2A | 70 | |
| α2B, α2C | Template:Abbr | |
| β1–β3 | Template:Abbr | |
| D1 | 13,000 | |
| D2 | 2,700 | |
| D3 | 5,000 | |
| D4, D5 | Template:Abbr | |
| H1 | 6,100 | |
| 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">{{#invoke:citation/CS1|citation | CitationClass=web
}}</ref><ref name="RickliLuethiReinisch2015">Template:Cite journal</ref><ref name="EshlemanForsterWolfrum2014">Template:Cite journal</ref><ref name="RudinLuethiHoener2022">Template:Cite journal</ref><ref name="PottieCannaertStove2020">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="EshlemanForsterWolfrum2014" /><ref name="RickliLuethiReinisch2015" />
2C-I is a highly potent anti-inflammatory drug similarly to various other serotonergic psychedelics.<ref name="FlanaganBillacLandry2021">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="FlanaganBillacLandry2021" /> It was more potent than (R)-DOI in terms of anti-inflammatory activity.<ref name="FlanaganBillacLandry2021" />
ChemistryEdit
Analogues and derivativesEdit
Template:2C-I analogues and derivatives
Society and cultureEdit
Legal statusEdit
AustraliaEdit
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>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
CanadaEdit
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 UnionEdit
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">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
FinlandEdit
Illegal: scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs".<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
SwedenEdit
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>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
United KingdomEdit
In the United Kingdom, 2C-I is controlled as a Class A substance.<ref name="erowid-law" />
United StatesEdit
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>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
See alsoEdit
ReferencesEdit
External linksEdit
- 2C-I - Isomer Design
- 2C-I - PsychonautWiki
- Erowid 2C-I Vault
- 2C-I Entry in PiHKAL
- 2C-I Entry in PiHKAL • info
- 2C-I: An Obscure, But Powerful Research Chemical - Tripsitter
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