Contents

2C-I

2C-I

Names
Preferred IUPAC name 2-(4-Iodo-2,5-dimethoxyphenyl)ethan-1-amine
Identifiers
CAS Number	69587-11-7 N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL338297 Y
ChemSpider	8442670 Y
ECHA InfoCard	100.217.507
KEGG	C22776 N
PubChem CID	10267191
UNII	S35362848V N
CompTox Dashboard (EPA)	DTXSID80893674
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 InChI=1/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 Key: PQHQBRJAAZQXHL-UHFFFAOYAK
SMILES Ic1cc(OC)c(cc1OC)CCN
Properties
Chemical formula	C10H14INO2
Molar mass	307.131 g·mol−1
Melting point	246 °C (475 °F; 519 K)
Pharmacology
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics) CA: Schedule III UK: Class A US: Schedule I
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

2C-I (2,5-Dimethoxy-4-iodophenethylamine) is a phenethylamine of the 2C family with psychedelic properties, primarily used as a recreational drug.^[1] 2C-I substance has been 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 illicit market in a powder or liquid 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]

Patterns of use[edit]

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]

Drug prohibition laws[edit]

European Union[edit]

In December 2003, the European Council issued a binding order compelling all EU member states to ban 2C-I within three months.^[7]

Canada[edit]

As of October 31, 2016, 2C-I is a controlled substance (Schedule III) in Canada.^[8]

Australia[edit]

2C-I is a schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).^[9] 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".^[10]

Sweden[edit]

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.^[11]

United Kingdom[edit]

In the United Kingdom, 2C-I is controlled as a Class A substance.^[7]

United States[edit]

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.^[7] 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.^[12]

Analogues and derivatives[edit]

DOI

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^[13]

See also[edit]

• Recreational drug use

References[edit]

External links[edit]

• Erowid 2C-I Vault
• Una experiencia con 2C-I de los Shulgin (In Spanish)
• 2C-I Entry in PiHKAL
• 2C-I Entry in PiHKAL • info