DOB-NBOMe, or NBOMe-DOB, also known as N-(2-methoxybenzyl)-4-bromo-2,5-dimethoxyamphetamine, is a serotonin 5-HT2A receptor agonist and possible psychedelic drug of the phenethylamine, DOx, and 25-NB (NBOMe) families. It is the N-(2-methoxybenzyl) derivative of DOB and the amphetamine (i.e., α-methyl) analogue of 25B-NBOMe.

Pharmacology

The drug is a potent serotonin 5-HT2A receptor partial agonist, with an EC50Tooltip half-maximal effective concentration of 7.94nM and an EmaxTooltip half-maximal effective concentration of 20% in the employed assay. As an agonist of the serotonin 5-HT2A receptor, DOB-NBOMe had about the same potency as DOB but had greatly reduced efficacy in comparison in vitro (with DOB having an EC50 of 10.2nM and an Emax of 71%). Compared to 25B-NBOMe, the corresponding NBOMe analogue of 2C-B, DOB-NBOMe had about 30-fold lower potency as a serotonin 5-HT2A receptor agonist and about half the activational efficacy. 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.

History

DOB-NBOMe was first described in the scientific literature by Ralf Heim by 2003.

See also

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