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Serotonin receptor modulator · 5-HT2A receptor agonist · 5-HT2C receptor agonist

5-DM-25B-NBOMe

Original Wikipedia articleen.wikipedia.org/wiki/5-DM-25B-NBOMe revision used (24 October 2026)

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Part of the metabolic pathway of 25B-NBOMe. See the timeline on the metabolic highway.

Overview

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), EC₅₀ (half-maximal effective concentration), and Eₘₐₓ (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.[1–7] WP

Drug class

Serotonin receptor modulator 5-HT2A receptor agonist 5-HT2C receptor agonist WP

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Chemistry

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Sources

  1. Journal / agency Duan W, Cao D, Wang S, Cheng J. Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants. Chemical Reviews. January 2024. doi:10.1021/acs.chemrev.3c00375 · PMID 38033123
  2. Journal / agency Leth-Petersen S, Petersen IN, Jensen AA, Bundgaard C, Bæk M, Kehler J, Kristensen JL. 5-HT2A/5-HT2C Receptor Pharmacology and Intrinsic Clearance of N-Benzylphenethylamines Modified at the Primary Site of Metabolism. ACS Chemical Neuroscience. November 2016. doi:10.1021/acschemneuro.6b00265 · PMID 27564969
  3. Journal / agency Marcher-Rørsted E, Halberstadt AL, Klein AK, Chatha M, Jademyr S, Jensen AA, Kristensen JL. Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists. ACS Chemical Neuroscience. May 2020. doi:10.1021/acschemneuro.0c00129 · PMID 32212672
  4. Journal / agency Poulie CB, Jensen AA, Halberstadt AL, Kristensen JL. DARK Classics in Chemical Neuroscience: NBOMes. ACS Chemical Neuroscience. December 2020. doi:10.1021/acschemneuro.9b00528 · PMID 31657895 · PMC9191638
  5. Journal / agency Halberstadt AL. Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens. Current Topics in Behavioral Neurosciences. 2017. doi:10.1007/7854_2016_64 · PMID 28097528
  6. Journal / agency Leth-Petersen S, Gabel-Jensen C, Gillings N, Lehel S, Hansen HD, Knudsen GM, Kristensen JL. Metabolic Fate of Hallucinogenic NBOMes. Chemical Research in Toxicology. January 2016. doi:10.1021/acs.chemrestox.5b00450 · PMID 26669514
  7. Journal / agency Boumrah Y, Humbert L, Phanithavong M, Khimeche K, Dahmani A, Allorge D. In vitro characterization of potential CYP- and UGT-derived metabolites of the psychoactive drug 25B-NBOMe using LC-high resolution MS. Drug Testing and Analysis. February 2016. doi:10.1002/dta.1865 · PMID 26382567

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