2C-I

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| _legal_data=Schedule 9F2Schedule IIIClass ASchedule I

| _other_data=2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine

| _image_0_or_2 = 2C-I2DACS.svg2C-I-3d-sticks.png | _image_LR =

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2C-I, also known as 2,5-dimethoxy-4-iodophenethylamine, is a phenethylamine of the 2C family with psychedelic effects.[1] 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.[2][3][4]

Use

In the early 2000s, 2C-I was sold in Dutch smart shops as a recreational drug after the drug 2C-B was banned.[5]

According to the US Drug Enforcement Administration, 2C-I is taken orally or snorted in a powder form.[6]

Interactions

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2C-I is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.[7][8] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-I.[7][8][9] This may result in overdose and serious toxicity.[9][7]

Pharmacology

Pharmacodynamics

2C-I activities
Target Affinity (Ki, nM)
5-HT1A 180–970 (Ki)
4,900 (Template:Abbrlink)
102% (Template:Abbrlink)
5-HT1B ND
5-HT1D ND
5-HT1E ND
5-HT1F ND
5-HT2A 3.5–9.3 (Ki)
1.48–513 (EC50)
17–93% (Emax)
5-HT2B 19.1–150 (EC50)
70–101% (Emax)
5-HT2C 10–40 (Ki)
0.46–537 (EC50)
44–107% (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 ND
5-HT7 ND
α1A 5,100
α1B, α1D ND
α2A 70
α2B, α2C ND
β1–β3 ND
D1 13,000
D2 2,700
D3 5,000
D4, D5 ND
H1 6,100
Template:Abbrlink 3,300 (Ki) (mouse)
120 (Ki) (rat)
2,400 (EC50) (mouse)
190 (EC50) (rat)
>10,000 (EC50) (human)
51% (Emax) (mouse)
50% (Emax) (rat)
Template:Abbrlink 950–4,900 (Ki)
5,600–13,000 (Template:Abbrlink)
IA (EC50)
Template:Abbrlink 15,000 (Ki)
22,000 (IC50)
IA (EC50)
Template:Abbrlink >30,000 (Ki)
126,000 (IC50)
IA (EC50)
Template:Abbrlink 125,000 (IC50)
Template:Abbrlink 55,000 (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [10][11][12][13][14]
[15][16][17][18][19][20]

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.[12][11]

2C-I is a highly potent anti-inflammatory drug similarly to various other serotonergic psychedelics.[18] However, 2C-I showed the highest anti-inflammatory potency of any other assessed drug in a large series in one study.[18] It was more potent than (R)-DOI in terms of anti-inflammatory activity.[18]

Chemistry

Analogues and derivatives

Template:2C-I analogues and derivatives

Society and culture

Legal status

File:2C-I Powder.jpg
2C-I in powder form.

Australia

2C-I is a schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[21] 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".[22]

Canada

As of October 31, 2016, 2C-I is a controlled substance (Schedule III) in Canada.[23]

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.[24]

Finland

Illegal: scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs".[25]

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.[26]

United Kingdom

In the United Kingdom, 2C-I is controlled as a Class A substance.[24]

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.[24] 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.[27]

See also

References

Template:Reflist

External links

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  1. ↑ Script error: No such module "Citation/CS1".
  2. ↑ Script error: No such module "citation/CS1".
  3. ↑ Weiss, Piper (September 20, 2012). 2C-I or 'Smiles': The New Killer Drug Every Parent Should Know About. Yahoo! News
  4. ↑ Script error: No such module "citation/CS1". WISH-TV
  5. ↑ Script error: No such module "Citation/CS1".
  6. ↑ Reuters (March 20, 2011). Synthetic drug, subject of proposed bans, kill teen.
  7. ↑ a b c Script error: No such module "Citation/CS1".
  8. ↑ a b Script error: No such module "Citation/CS1".
  9. ↑ a b Script error: No such module "Citation/CS1".
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  11. ↑ a b Script error: No such module "Citation/CS1".
  12. ↑ a b Script error: No such module "Citation/CS1".
  13. ↑ Script error: No such module "Citation/CS1".
  14. ↑ Script error: No such module "Citation/CS1".
  15. ↑ Script error: No such module "Citation/CS1".
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  18. ↑ a b c d Script error: No such module "Citation/CS1".
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  20. ↑ Script error: No such module "Citation/CS1".
  21. ↑ Poisons Standard October 2015
  22. ↑ Script error: No such module "citation/CS1".
  23. ↑ Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)
  24. ↑ a b c Script error: No such module "citation/CS1".
  25. ↑ Script error: No such module "citation/CS1".
  26. ↑ Script error: No such module "citation/CS1".
  27. ↑ Script error: No such module "citation/CS1".
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