DOI-NBOMe

DOI-NBOMe, or NBOMe-DOI, also known as N-(2-methoxybenzyl)-4-iodo-2,5-dimethoxyamphetamine, is a serotonin 5-HT_2A receptor agonist and possible psychedelic drug of the phenetylamine, DOx, and 25-NB (NBOMe) families.^{[1][2][3][4][5]} It is the N-(2-methoxybenzyl) derivative of DOI and the amphetamine (i.e., α-methyl) analogue of 25I-NBOMe.^[4][3][5]

DOI-NBOMe

Clinical data
Other names	NBOMe-DOI; N-(2-Methoxybenzyl)-4-iodo-2,5-dimethoxyamphetamine; 4-Iodo-2,5-dimethoxy-N-(2-methoxybenzyl)amphetamine
Drug class	Serotonin 5-HT2A receptor partial agonist; Serotonin 5-HT2C receptor ligand; Possible serotonergic psychedelic or hallucinogen
ATC code	None
Identifiers
IUPAC name 1-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]propan-2-amine
PubChem CID	169776666
Chemical and physical data
Formula	C19H24INO3
Molar mass	441.309 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1cc(I)c(cc1CC(NCc1ccccc1OC)C)OC
InChI InChI=1S/C19H24INO3/c1-13(21-12-14-7-5-6-8-17(14)22-2)9-15-10-19(24-4)16(20)11-18(15)23-3/h5-8,10-11,13,21H,9,12H2,1-4H3 Key:XRQNUXKKHOVYIR-UHFFFAOYSA-N

Pharmacology

The drug is a potent serotonin 5-HT_2A receptor partial agonist, with an affinity (K_i) of 0.78 to 1.08 nM, an EC₅₀Tooltip half-maximal effective concentration of 36.1 nM, and an E_maxTooltip half-maximal effective concentration of 43% in the employed assay.^[4][3] As an agonist of the serotonin 5-HT_2A receptor, DOI-NBOMe had about half the affinity and potency of DOI and a little more than half the efficacy in comparison in vitro (with DOI having a K_i of 0.58–0.64 nM, an EC₅₀ of 19.2 nM, and an E_max of 77%).^[4][3] Compared to 25I-NBOMe, the corresponding NBOMe analogue of 2C-I, DOI-NBOMe had about 14.4-fold lower potency as a serotonin 5-HT_2A receptor agonist and slightly more than half the activational efficacy.^[4][3] Whereas the potency of 2Cs can be dramatically increased by N-(2-methoxybenzyl) substitution, this has not been the case with the DOx series of psychedelics, where activity has been negatively impacted.^{[2][4][3][5][6][7]}

Besides the serotonin 5-HT_2A receptor, DOI-NBOMe has also been shown to bind to the serotonin 5-HT_2C receptor, with an affinity (K_i) of 21.0 nM.^[3] This was about 33-fold lower than the affinity of DOI.^[3] As such, DOI-NBOMe appears to show increased selectivity for the serotonin 5-HT_2A receptor over the serotonin 5-HT_2C receptor compared to DOI.^[3] For comparison, 25I-NBOMe had increased affinities for both the serotonin 5-HT_2A receptor and to a lesser extent the serotonin 5-HT_2C receptor compared to 2C-I.^[3]

History

DOI-NBOMe was first described in the scientific literature by Ralf Heim by 2003.^[5] However, Heim only synthesized DOI-NBOMe without reporting its pharmacology.^[5] The pharmacological interactions of DOI-NBOMe were subsequently reported by Michael Braden and colleagues, from the lab of David E. Nichols, by 2006.^[4][3]

See also

• DOB-NBOMe
• DOM-NBOMe
• 25-NB
• DOx