2C-I

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).

2C-I

Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics) CA: Schedule III UK: Class A US: Schedule I
Identifiers
IUPAC name 2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine
CAS Number	69587-11-7 Y
PubChem CID	10267191
ChemSpider	8442670 Y
UNII	S35362848V
KEGG	C22776 Y
ChEMBL	ChEMBL338297 Y
CompTox Dashboard (EPA)	DTXSID80893674
ECHA InfoCard	100.217.507
Chemical and physical data
Formula	C10H14INO2
Molar mass	307.131 g·mol−1
3D model (JSmol)	Interactive image
Melting point	246 °C (475 °F)
SMILES Ic1cc(OC)c(cc1OC)CCN
InChI InChI=1S/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 Y Key:PQHQBRJAAZQXHL-UHFFFAOYSA-N Y
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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

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

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 (EC50Tooltip half-maximal effective concentration) 102% (EmaxTooltip maximal efficacy)
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
TAAR1Tooltip Trace amine-associated receptor 1	3,300 (Ki) (mouse) 120 (Ki) (rat) 2,400 (EC50) (mouse) 190 (EC50) (rat) >10,000 (EC50) (human) 51% (Emax) (mouse) 50% (Emax) (rat)
SERTTooltip Serotonin transporter	950–4,900 (Ki) 5,600–13,000 (IC50Tooltip half-maximal inhibitory concentration) IA (EC50)
NETTooltip Norepinephrine transporter	15,000 (Ki) 22,000 (IC50) IA (EC50)
DATTooltip Dopamine transporter	>30,000 (Ki) 126,000 (IC50) IA (EC50)
MAO-ATooltip Monoamine oxidase A	125,000 (IC50)
MAO-BTooltip Monoamine oxidase B	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]

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.^[12][11]

2C-I is a highly potent anti-inflammatory drug similarly to various other serotonergic psychedelics.^[17] However, 2C-I showed the highest anti-inflammatory potency of any other assessed drug in a large series in one study.^[17] It was more potent than (R)-DOI in terms of anti-inflammatory activity.^[17]

Chemistry

Analogues and derivatives

DOI

Analogues and derivatives of 2C-I:

25I-NB*:

• 25I-NBF
• 25I-NBMD
• 25I-NB34MD
• 25I-NBOH
• 25I-NBOMe (NBOMe-2CI)
• 25I-NB3OMe
• 25I-NB4OMe

N-(2C)-fentanyl:

• N-(2C-I) fentanyl^[20]

Society and culture

Legal status

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]

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.^[25]

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.^[26]

See also

• Recreational drug use