N-Methyl-DOI

N-Methyl-DOI
Clinical data
Other names	2,5-Dimethoxy-4-iodo-N-methylamphetamine; 4-Iodo-2,5-dimethoxy-N-methylamphetamine; 2,5-IDNA; N-Me-DOI
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor partial agonist
ATC code	None;
Identifiers
	IUPAC name 1-(4-iodo-2,5-dimethoxyphenyl)-N-methylpropan-2-amine;
PubChem CID	44267102;
ChemSpider	23110915;
ChEMBL	ChEMBL10968;
Chemical and physical data
Formula	C12H18INO2
Molar mass	335.185 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC(=C(C=C1OC)I)OC)NC;
	InChI InChI=1S/C12H18INO2/c1-8(14-2)5-9-6-12(16-4)10(13)7-11(9)15-3/h6-8,14H,5H2,1-4H3; Key:UFHCKYRPMINDBF-UHFFFAOYSA-N;

N-Methyl-DOI, also known as 2,5-dimethoxy-4-iodo-N-methylamphetamine (2,5-IDNA), is a serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families related to the serotonergic psychedelic DOI.^[1]^[2] It is a potent agonist of the serotonin 5-HT_2A receptor similarly to DOI.^[1] However, N-methyl-DOI was about 3.8-fold less potent than DOI as a serotonin 5-HT_2A receptor agonist in terms of EC₅₀Tooltip half-maximal effective concentration and showed reduced maximal efficacy compared to DOI (E_maxTooltip maximal efficacy = 64% vs. 83%).^[1] On the other hand, it showed similar efficacy in activating the serotonin 5-HT_2A receptor to the psychedelic 2C-I (E_max = 68%).^[1] N-Methyl-DOI was first described in the scientific literature, as a potential radiopharmaceutical for medical imaging, by Alexander Shulgin and colleagues by 1984.^[3]

References

^ ^a ^b ^c ^d McCorvy JD (16 January 2013). Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics (Ph.D. thesis). Purdue University. Archived from the original on 25 March 2025 – via Purdue e-Pubs.
^ Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
^ Sargent T, Shulgin AT, Mathis CA (August 1984). "Radiohalogen-labeled imaging agents. 3. Compounds for measurement of brain blood flow by emission tomography". Journal of Medicinal Chemistry. 27 (8): 1071–1077. doi:10.1021/jm00374a023. PMID 6611416.

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