DOM-NBOMe, or NBOMe-DOM, also known as N-(2-methoxybenzyl)-4-methyl-2,5-dimethoxyamphetamine, is a serotonin 5-HT2 receptor agonist and putative psychedelic drug of the phenethylamine, DOx, and 25-NB (NBOMe) families. Table 1. 5-HT2A receptor binding affinities of disclosed compounds. Table 3. Functional activity at 5-HT receptor subtypes. [...] Table 4. Activity in the HTR assay in mice. [...] It is the N-(2-methoxybenzyl) derivative of DOM and the amphetamine (i.e., α-methyl) analogue of 25D-NBOMe.
Pharmacology Pharmacodynamics DOM-NBOMe is a potent agonist of the serotonin 5-HT2 receptors, including the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. Its affinity (Ki) for the serotonin 5-HT2A receptor was reported to be 45.8nM. In terms of functional activity, DOM-NBOMe showed an of 4.25nM and of 88.8% at the serotonin 5-HT2A receptor, an of 54.6nM and of 20.1% at the serotonin 5-HT2B receptor, and an of 9.96nM and of 87.6% at the serotonin 5-HT2C receptor. It was inactive as an agonist of the serotonin 5-HT1A receptor, with an of >10,000nM. DOM-NBOMe showed 17-fold lower potency as a serotonin 5-HT2A receptor agonist compared to 25D-NBOMe in vitro, while DOM was not assessed in the same study and thus DOM-NBOMe could not be compared to that compound. 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.
DOM-NBOMe has been assessed and found to produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. However, DOM-NBOMe showed a weak maximal head-twitch response compared to DOI. Whereas DOI induced a maximum of 36 head twitches in a 20-minute period, DOM-NBOMe produced a maximum of 12 head twitches in the same amount of time (i.e., about 33% of that of DOI). Hence, although DOM-NBOMe could still be an active psychedelic in humans, it may have attenuated hallucinogenic effects compared to non-25-NB DOx psychedelics. The doses of DOM-NBOMe producing the head-twitch response were not reported.
Pharmacokinetics The in-vitro metabolism and cytochrome P450 (CYP450) inhibition of DOM-NBOMe have been studied.
History DOM-NBOMe was first disclosed in a patent application (compound #17, example #16 in WO2022/192781) by Andrew Kruegel at Gilgamesh Pharmaceuticals by 2022.
See also DOB-NBOMe DOI-NBOMe NBOMe-mescaline 5-APB-NBOMe 25D-NM-NDEAOP 25-NB DOx
References
External links DOM-NBOMe - Isomer Design