5-DM-25B-NBOMe

5-DM-25B-NBOMe
Clinical data
Other names5-O-Desmethyl-25B-NBOMe; 5-OH-25B-NBOMe; N-(2-Methoxybenzyl)-4-bromo-5-hydroxy-2-methoxyphenethylamine
Drug classSerotonin receptor modulator; 5-HT2A receptor agonist; 5-HT2C receptor agonist
ATC code
  • None
Identifiers
  • 2-bromo-4-methoxy-5-(2-{[(2-methoxyphenyl)methyl]amino}ethyl)phenol
Chemical and physical data
FormulaC17H20BrNO3
Molar mass366.255 g·mol−1
3D model (JSmol)
  • COC1=C(CCN([H])CC2=C(OC)C=CC=C2)C=C(O[H])C(Br)=C1
  • InChI=1S/C17H20BrNO3/c1-21-16-6-4-3-5-13(16)11-19-8-7-12-9-15(20)14(18)10-17(12)22-2/h3-6,9-10,19-20H,7-8,11H2,1-2H3
  • Key:IVVHUBRWCYPDHE-UHFFFAOYSA-N

5-DM-25B-NBOMe, also known as 5-O-desmethyl-25B-NBOMe, is a serotonin receptor modulator of the phenethylamine family related to the NBOMe psychedelic 25B-NBOMe. It is the 5-O-desmethyl analogue of 25B-NBOMe. The drug is a potent agonist of the serotonin 5-HT2A and 5-HT2C receptors. Its affinity (Ki), EC50Tooltip half-maximal effective concentration, and EmaxTooltip maximal efficacy values at the serotonin 5-HT2A receptor were 2.24 nM, 1.20 nM, and 61%, respectively, whereas its values at the serotonin 5-HT2C receptor were 10.5 nM, 0.617 nM, and 73%, respectively. At the serotonin 5-HT2A receptor, the drug showed 11-fold lower affinity, 1.3-fold lower activational potency, and a numerical efficacy decrease of 22% compared to 25B-NBOMe. It is a major metabolite of 25B-NBOMe and is formed by cytochrome P450 enzymes. 5-DM-25B-NBOMe was first described in the scientific literature by 2016.

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