N-Methyl-DOI
N-Methyl-DOI, also known as 2,5-dimethoxy-4-iodo-N-methylamphetamine, is a serotonin [receptor modulator] of the phenethylamine, amphetamine, and DOx families related to the serotonergic psychedelic DOI. It is a potent agonist of the serotonin 5-HT2A receptor similarly to DOI. However, N-methyl-DOI was about 3.8-fold less potent than DOI as a serotonin 5-HT2A receptor agonist in terms of and showed reduced maximal efficacy compared to DOI. On the other hand, it showed similar efficacy in activating the serotonin 5-HT2A receptor to the psychedelic 2C-I. N-Methyl-DOI was first described in the scientific literature, as a potential radiopharmaceutical for medical imaging, by Alexander Shulgin and colleagues by 1984. It is a controlled substance in Canada under phenethylamine blanket-ban language.