Chemistry:5-DM-25B-NBOMe

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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.[1][2][3] It is the 5-O-desmethyl analogue of 25B-NBOMe.[1][2] The drug is a potent agonist of the serotonin 5-HT2A and 5-HT2C receptors.[2] Its affinity (Ki), EC50, and Emax 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.[2] 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.[2] It is a major metabolite of 25B-NBOMe and is formed by cytochrome P450 enzymes.[4][5][6][7] 5-DM-25B-NBOMe was first described in the scientific literature by 2016.[2][6][7]

See also

References

  1. ↑ 1.0 1.1 "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews 124 (1): 124–163. January 2024. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. "In order to increase the metabolic stability of NBOMes, compounds such as 115−122 were reported in 2016.181 [...]". 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "5-HT2A/5-HT2C Receptor Pharmacology and Intrinsic Clearance of N-Benzylphenethylamines Modified at the Primary Site of Metabolism". ACS Chemical Neuroscience 7 (11): 1614–1619. November 2016. doi:10.1021/acschemneuro.6b00265. PMID 27564969. 
  3. ↑ "Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists". ACS Chemical Neuroscience 11 (9): 1238–1244. May 2020. doi:10.1021/acschemneuro.0c00129. PMID 32212672. "To our surprise, removal of the 5-methoxy group from the NBOMescaffold resulted in only a 10-fold decrease in 5-HT2AR binding affinity compared to the parent compound 20 (pKi = 9.68 and 8.68, respectively), whereas the effect on agonist potency and agonist efficacy was even smaller (20: pEC50 = 9.04, Rmax = 83%; 22: pEC50 = 8.87, Rmax = 70%).". 
  4. ↑ "DARK Classics in Chemical Neuroscience: NBOMes". ACS Chemical Neuroscience 11 (23): 3860–3869. December 2020. doi:10.1021/acschemneuro.9b00528. PMID 31657895. "In a follow-up study, five phase I metabolites of 25B-NBOMe were identified. All three O-demethylated metabolites (4−6) were found in approximately the same abundancies, as were the hydroxylated metabolites (7−8), albeit with relatively lower abundancy. 2CB, the N-debenzylated metabolite, was also detected, but it also had lower abundancy.107 [...] Scheme 3. Putative Phase I Metabolic Pathways for 25BNBOMe in Humans [...]". 
  5. ↑ "Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens". Current Topics in Behavioral Neurosciences 32: 283–311. 2017. doi:10.1007/7854_2016_64. ISBN 978-3-319-52442-9. PMID 28097528. "NBOMes are extensively metabolized. Caspar et al. tentatively identified 37 phase I and 31 phase II metabolites of 25I-NBOMe in rat and human urine [125]. The primary metabolites of 25I-NBOMe are 2-O-desmethyl-25I-NBOMe, 5-O-desmethyl-25INBOMe, 25I-NBOH, and their glucuronic acid conjugates [125–128]. Similar findings have been reported for 25B-NBOMe and 25C-NBOMe [128–130]. CYP3A4 is the major cytochrome P450 isoenzyme responsible for the biotransformation of 25INBOMe, with CYP2C9 and CYP2C19 potentially also contributing [125, 126].". 
  6. ↑ 6.0 6.1 "Metabolic Fate of Hallucinogenic NBOMes". Chemical Research in Toxicology 29 (1): 96–100. January 2016. doi:10.1021/acs.chemrestox.5b00450. PMID 26669514. 
  7. ↑ 7.0 7.1 "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 8 (2): 248–256. February 2016. doi:10.1002/dta.1865. PMID 26382567. 



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