2C-I

2C-I
Names
	Preferred IUPAC name 2-(4-Iodo-2,5-dimethoxyphenyl)ethan-1-amine
Identifiers
CAS Number	69587-11-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL338297 ;
ChemSpider	8442670 ;
ECHA InfoCard	100.217.507
KEGG	C22776 ;
PubChem CID	10267191;
UNII	S35362848V ;
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 Key: PQHQBRJAAZQXHL-UHFFFAOYSA-N ; 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). verify (what is ?) Infobox references

2C-I (2,5-Dimethoxy-4-iodophenethylamine) is a phenethylamine of the 2C family with psychedelic properties.^[1] 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.^[2]^[3]^[4]

^ Bosak, Adam; LoVecchio, Frank; Levine, Michael (June 2013). "Recurrent Seizures and Serotonin Syndrome Following "2C-I" Ingestion". Journal of Medical Toxicology. 9 (2): 196–198. doi:10.1007/s13181-013-0287-x. ISSN 1556-9039. PMC 3657032. PMID 23378129.
^ "25I-NBOMe (2C-I-NBOMe): Fatalities / Deaths".
^ Weiss, Piper (September 20, 2012). 2C-I or 'Smiles': The New Killer Drug Every Parent Should Know About. Yahoo! News
^ Mackin, Teresa (October 9, 2012). Dangerous synthetic drug making its way across the country. Archived October 31, 2012, at the Wayback Machine WISH-TV

[1] Bosak, Adam; LoVecchio, Frank; Levine, Michael (June 2013). "Recurrent Seizures and Serotonin Syndrome Following "2C-I" Ingestion". Journal of Medical Toxicology. 9 (2): 196–198. doi:10.1007/s13181-013-0287-x. ISSN 1556-9039. PMC 3657032. PMID 23378129.

[2] "25I-NBOMe (2C-I-NBOMe): Fatalities / Deaths".

[weiss-3] Weiss, Piper (September 20, 2012). 2C-I or 'Smiles': The New Killer Drug Every Parent Should Know About. Yahoo! News

[mackin2012-4] Mackin, Teresa (October 9, 2012). Dangerous synthetic drug making its way across the country. Archived October 31, 2012, at the Wayback Machine WISH-TV

[1]

[2]

[3]

[4]