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 ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...

'' (1991). The substance is consumed as a

recreational drug Recreational drug use is the use of one or more psychoactive drugs to induce an altered state of consciousness, either for pleasure or for some other casual purpose or pastime. When a psychoactive drug enters the user's body, it induces an Sub ...

, 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.Weiss, Piper (September 20, 2012)
2C-I or 'Smiles': The New Killer Drug Every Parent Should Know About.
'' Yahoo! News'' WISH-TV

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 The Drug Enforcement Administration (DEA) is a Federal law enforcement in the United States, United States federal law enforcement agency under the U.S. Department of Justice tasked with combating illicit Illegal drug trade, drug trafficking a ...

, 2C-I is taken orally or snorted in a powder form.Reuters (March 20, 2011)
Synthetic drug, subject of proposed bans, kill teen.
/ref>

Interactions

2C-I is metabolized by the

monoamine oxidase Monoamine oxidases (MAO) () are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine group. They are found bound to the outer membrane of mitochondria in most cell types of the body. The fi ...

(MAO)

enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...

s MAO-A and MAO-B.

Monoamine oxidase inhibitor Monoamine oxidase inhibitors (MAOIs) are a drug class, class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressa ...

s (MAOIs) such as

phenelzine Phenelzine, sold under the brand name Nardil among others, is a non-selective and irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine family which is primarily used as an antidepressant and anxiolytic to treat depression and a ...

tranylcypromine Tranylcypromine, sold under the brand name Parnate among others, is a monoamine oxidase inhibitor (MAOI). More specifically, tranylcypromine acts as nonselective and irreversible inhibitor of the enzyme monoamine oxidase (MAO). It is used a ...

moclobemide Moclobemide, sold under the brand names Amira, Aurorix, Clobemix, Depnil and Manerix among others, is a reversible inhibitor of monoamine oxidase A (RIMA) drug primarily used to treat Clinical depression, depression and social anxiety. It is not ...

, and selegiline may potentiate the effects of 2C-I. This may result in

overdose A drug overdose (overdose or OD) is the ingestion or application of a drug or other substance in quantities much greater than are recommended. Retrieved on September 20, 2014.

and serious

toxicity Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacteria, bacterium, or plant, as well as the effect o ...

Pharmacology

Pharmacodynamics

2C-I acts as a serotonin receptor

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

. 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 psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

s. 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

Analogues and derivatives

Society and culture

Legal status

Australia

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

Canada

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

European Union

In December 2003, the

European Council The European Council (informally EUCO) is a collegiate body (directorial system) and a symbolic collective head of state, that defines the overall political direction and general priorities of the European Union (EU). It is composed of the he ...

issued a binding order compelling all

European Union The European Union (EU) is a supranational union, supranational political union, political and economic union of Member state of the European Union, member states that are Geography of the European Union, located primarily in Europe. The u ...

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 The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

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.

References

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
{{Phenethylamines 5-HT2A agonists 5-HT2B agonists 5-HT2C agonists 2C (psychedelics) Designer drugs Iodobenzene derivatives O-methylated phenols Psychedelic phenethylamines TAAR1 agonists

Use