2C-I

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| _legal_data=Schedule 9F2Schedule IIIClass ASchedule I

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

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

Use

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

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

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

2C-I activities

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	ND
5-HT2A	3.5–9.3 (Ki) 1.48–513 (EC50) 17–93% (Emax)
5-HT2B	9.3 (Ki) 19.1–150 (EC50) 70–101% (Emax)
5-HT2C	9.3–40 (Ki) 0.46–537 (EC50) 44–107% (Emax)
5-HT3	>10,000
5-HT4	ND
5-HT5A	>10,000
5-HT6	ND
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	ND
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	ND
σ1	>10,000
σ2	5,470
MOR	2,522
DOR	ND
KOR	>10,000
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:

2C-I acts as a serotonin receptor agonist. It produces psychedelic effects via serotonin 5-HT_2A 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.

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). 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

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

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.

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

• Recreational drug use

External links

• 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