DOB-NBOMe

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

DOB-NBOMe

Clinical data
Other names	NBOMe-DOB; N-(2-Methoxybenzyl)-4-bromo-2,5-dimethoxyamphetamine; 4-Bromo-2,5-dimethoxy-N-(2-methoxybenzyl)amphetamine
Drug class	Serotonin 5-HT2A receptor partial agonist; Possible serotonergic psychedelic or hallucinogen
ATC code	None
Identifiers
IUPAC name 1-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]propan-2-amine
PubChem CID	169776410
Chemical and physical data
Formula	C19H24BrNO3
Molar mass	394.309 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1cc(Br)c(cc1CC(NCc1ccccc1OC)C)OC
InChI InChI=1S/C19H24BrNO3/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:VIURPEKIEYLSKF-UHFFFAOYSA-N

Pharmacology

The drug is a potent serotonin 5-HT_2A receptor partial agonist, with an EC₅₀Tooltip half-maximal effective concentration of 7.94 nM and an E_maxTooltip half-maximal effective concentration of 20% in the employed assay.^[1][2][3] As an agonist of the serotonin 5-HT_2A 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 10.2 nM and an E_max of 71%).^[1][2][3] Compared to 25B-NBOMe, the corresponding NBOMe analogue of 2C-B, DOB-NBOMe had about 30-fold lower potency as a serotonin 5-HT_2A receptor agonist and about half the activational efficacy.^[1][2][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.^{[4][5][6][1][2][3]}

History

DOB-NBOMe was first described in the scientific literature by Ralf Heim by 2003.^[1]

See also

• DOI-NBOMe
• DOM-NBOMe
• DMBMPP
• 25-NB
• DOx