2c-i 2c-i 2c-i is a psychedelic phenethylamine of the 2c family. it was first synthesized by alexander shulgin and described in his 1991 book pihkal (phenethylamines i have known and loved). the drug has been used recreationally as psychedelic and other reported effects and was sometimes confused with the more potent chemical cousin 25i-nbome, nicknamed "smiles," in the media. 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 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 ykey: pqhqbrjaazqxhl-uhfffaoysa-n yinchi=1/c10h14ino2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6h,3-4,12h2,1-2h3key: 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) 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 , 100 kpa). n verify (what is yn ?) infobox references recreational use the drug 2c-i in powder form in the early 2000s, 2c-i was sold in dutch smart shops 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. drug prohibition laws european union in december 2003, the european council issued a binding order compelling all eu member states to ban 2c-i within three months. canada as of october 31, 2016, 2c-i is a controlled substance (schedule iii) in canada. 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". 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. 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