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2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine of the phenethylamine family. It is also a powerful anti-inflammatory that is effective at doses on the order of 100 micrograms in humans, far below its effective dose as a psychedelic. Despite being a substituted amphetamine, it is not a stimulant. DOI has a stereocenter and R-(-)-DOI is the more active stereoisomer. DOI is a 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonist. Its psychedelic effects are mediated by its agonistic properties at the 5-HT2A receptor. This is a controlled substance.

ChEBI: An organoiodine compound that is amphetamine bearing two methoxy substituents at positions 2 and 5 as well as an iodo substituent at position 4.