N-Methyl-2C-I
N-Methyl-2C-I, also known as 25I-NMe or as N-methyl-4-iodo-2,5-dimethoxyphenethylamine, is a serotonin receptor modulator of the phenethylamine and 2C families related to the psychedelic drug 2C-I. It is specifically the N-methyl analogue of 2C-I.
The drug shows more than 2,500-fold reduced affinity for the serotonin 5-HT2A receptor compared to 2C-I. In addition, N-methyl-2C-I showed around 170-fold lower affinity for the serotonin 5-HT2C receptor relative to 2C-I. These results are in accordance with general findings that N-alkylation of psychedelic phenethylamines results in dramatic or complete losses of psychedelic and related activities. In contrast to simple N-alkylation however, the N-benzyl derivative of 2C-I, 25I-NB, showed similar affinity for the serotonin 5-HT2A receptor compared to 2C-I itself. Relatedly, the N- derivatives, such as 25I-NBOMe, have not only retained but greatly enhanced activity and constitute the extremely potent NBOMe family of psychedelics.
N-Methyl-2C-I was first described in the scientific literature by at least 2012. It is a controlled substance in Canada under phenethylamine blanket-ban language.