DOM-NBOMe

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.^[1] It is the N-(2-methoxybenzyl) derivative of DOM and the amphetamine (i.e., α-methyl) analogue of 25D-NBOMe.^[1]

DOM-NBOMe

Clinical data
Other names	NBOMe-DOM; N-(2-Methoxybenzyl)-4-methyl-2,5-dimethoxyamphetamine; 4-Methyl-2,5-dimethoxy-N-(2-methoxybenzyl)amphetamine
Drug class	Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name 1-(2,5-dimethoxy-4-methylphenyl)-N-[(2-methoxyphenyl)methyl]propan-2-amine
CAS Number	2836395-73-2
PubChem CID	165123639
ChemSpider	129677314
Chemical and physical data
Formula	C20H27NO3
Molar mass	329.440 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC(=C(C=C1OC)CC(C)NCC2=CC=CC=C2OC)OC
InChI InChI=1S/C20H27NO3/c1-14-10-20(24-5)17(12-19(14)23-4)11-15(2)21-13-16-8-6-7-9-18(16)22-3/h6-10,12,15,21H,11,13H2,1-5H3 Key:KWMCUFLLPHCVSK-UHFFFAOYSA-N

Pharmacology

Pharmacodynamics

DOM-NBOMe is a potent agonist of the serotonin 5-HT₂ receptors, including the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[1] Its affinity (K_i) for the serotonin 5-HT_2A receptor was reported to be 45.8 nM.^[1] In terms of functional activity, DOM-NBOMe showed an EC₅₀Tooltip half-maximal effective concentration of 4.25 nM and E_maxTooltip maximal efficacy of 88.8% at the serotonin 5-HT_2A receptor, an EC₅₀ of 54.6 nM and E_max of 20.1% at the serotonin 5-HT_2B receptor, and an EC₅₀ of 9.96 nM and E_max of 87.6% at the serotonin 5-HT_2C receptor.^[1] It was inactive as an agonist of the serotonin 5-HT_1A receptor, with an EC₅₀ of >10,000 nM.^[1] DOM-NBOMe showed 17-fold lower potency as a serotonin 5-HT_2A 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.^[1] 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][3][4][5][6][7]}

DOM-NBOMe has been assessed and found to produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.^[1] However, DOM-NBOMe showed a weak maximal head-twitch response compared to DOI.^[1] 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).^[1] 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.^[1] The doses of DOM-NBOMe producing the head-twitch response were not reported.^[1]

Pharmacokinetics

The in-vitro metabolism and cytochrome P450 (CYP450) inhibition of DOM-NBOMe have been studied.^[1]

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.^[1]

See also

• DOB-NBOMe
• DOI-NBOMe
• NBOMe-mescaline
• 25D-NM-NDEAOP
• 25-NB
• DOx