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.^[1][2] It is specifically the N-methyl analogue of 2C-I.^[1][2]

N-Methyl-2C-I

Clinical data
Other names	25I-NMe; N-Methyl-4-iodo-2,5-dimethoxyphenethylamine
Drug class	Serotonin receptor modulator
ATC code	None
Identifiers
IUPAC name 2-(4-iodo-2,5-dimethoxyphenyl)-N-methylethan-1-amine
Chemical and physical data
Formula	C11H16INO2
Molar mass	321.158 g·mol−1
3D model (JSmol)	Interactive image
SMILES CNCCc1cc(OC)c(cc1OC)I
InChI InChI=1S/C11H16INO2/c1-13-5-4-8-6-11(15-3)9(12)7-10(8)14-2/h6-7,13H,4-5H2,1-3H3 Key:VKPKTPYPZITMRK-UHFFFAOYSA-N

The drug shows more than 2,500-fold reduced affinity for the serotonin 5-HT_2A receptor compared to 2C-I.^[1][2] In addition, N-methyl-2C-I showed around 170-fold lower affinity for the serotonin 5-HT_2C receptor relative to 2C-I.^[1][2] 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.^[1][2] In contrast to simple N-alkylation however, the N-benzyl derivative of 2C-I, 25I-NB (N-benzyl-2C-I), showed similar affinity for the serotonin 5-HT_2A receptor compared to 2C-I itself.^[1][2][3] Relatedly, the N-(2-methoxybenzyl) derivatives, such as 25I-NBOMe, have not only retained but greatly enhanced activity and constitute the extremely potent NBOMe family of psychedelics.^[1][4][5]

N-Methyl-2C-I was first described in the scientific literature by at least 2012.^[2]

See also

• 2C (psychedelics)
• N-Methyl-2C-B
• N-Ethyl-2C-B
• N-Methyl-DOI
• IDNNA (N,N-dimethyl-DOI)
• N-Methylmescaline