2C-I

2C-I
Clinical data
Other names	4-Iodo-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-iodophenethylamine; 25I; Cimbi-88; 2C-DOI
Routes of; administration	Oral
Drug class	Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule III; UK: Class A; US: Schedule I;
Pharmacokinetic data
Onset of action	≤40 minutes
Duration of action	6–10 hours
Identifiers
	IUPAC name 2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine;
CAS Number	69587-11-7 ;
PubChem CID	10267191;
ChemSpider	8442670 ;
UNII	S35362848V;
KEGG	C22776 ;
ChEMBL	ChEMBL338297 ;
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 ; Key:PQHQBRJAAZQXHL-UHFFFAOYSA-N ;
	(verify)

2C-I, also known as 4-iodo-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It is taken orally.

2C-I was first synthesized and described by Alexander Shulgin in 1977 and was described in further detail in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). The drug is used recreationally. 2C-I is sometimes confused with other related psychedelic drugs such as 25I-NBOMe (NBOMe-2C-I), nicknamed "Smiles" and "N-bomb" in the media.