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2,5-Dimethoxy-4-iodoamphetamine (also known as DOI) is a lesser-known psychedelic substance of the phenethylamine class. It is a member of the DOx family of psychedelic amphetamines.

The synthesis of DOI was first reported in 1972 and its usage in humans was first documented by Alexander Shulgin in the 1991 book PiHKAL (“Phenethylamines I Have Known and Loved”). DOI is very well-researched compared to most psychedelics. It is regularly used in research as a radioligand to map serotonin-2A receptors in the brain.

The effects of DOI are often compared to those of LSD, although notable differences can be distinguished. Besides the significantly longer duration, the experience is commonly reported to be more stimulating than LSD, with a more pronounced body load and a less complex head space. The after effects include long-lasting residual stimulation and difficulty sleeping, which, depending on the dose and time taken during the day, may persist for days afterwards.

DOI is sometimes sold as a substitute for LSD, or even sold falsely as LSD. This can be dangerous because DOI does not have the same established safety profile as LSD.

Along with its sensitive dose-response and unusually long duration, many reports also suggest that this substance may be overly difficult to use safely for those who are not already experienced with psychedelics. Therefore it is highly advised to approach this highly dose-sensitive, and long-lasting psychedelic substance with the proper amount of precaution and harm reduction practices if using it.

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DOI, or 2,5-Dimethoxy-4-iodoamphetamine, is a molecule of the amphetamine class. Amphetamines are substituted phenethylamines containing a phenyl ring bound to an amino (NH2) group through an ethyl chain and a methyl group bound to the alpha carbon Rα. DOI contains methoxy functional groups OCH3 attached to carbons R2 and R5 as well as an iodine atom attached to carbon R4 of the phenyl ring. DOI is the amphetamine, or alpha-methylated analogue, of the phenethylamine 2C-I.

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