Chemistry:24-NB

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The 24-NB (24x-NBOMe) series is a little-known family of serotonin receptor modulators and possible serotonergic psychedelics that are primarily substituted phenethylamines or positional isomers of members of the 25-NB family. The best known representative is 24H-NBOMe, which is a potent, selective, full agonist of 5-HT2A receptor, with a potency approximately equal to or even greater than 25H-NBOMe, other well-known compounds in this family also include 24H-NBF.[1][2][3][4]

The 24-NBOMe series compounds are positional isomers in which two methoxy groups are fixed at the 2- and 4-positions of the phenyl ring of the phenylethylamine moiety.

Pharmacology

Pharmacodynamics

In vitro, the 24H-NBOMe isomer exhibits high agonistic activity against 5-HT2A receptors, exceeding in potency (EC50= 3.88 nM) the standard 25H-NBOMe (EC50=11.4 nM) and demonstrating comparable efficacy (Emax = 145%) relative to LSD.[1][2] In in vivo studies in fish, 24H-NBOMe caused anxiety in fish and showed potent behavioral effects.[3]

In vitro, 24H-NBF showed the highest activity (EC50) = 158 nM) towards 5-HT2A, significantly exceeding the reference 25H-NBF (EC50) = 448 nM) and demonstrating a Emax (107%) similar to LSD.[4] Virtually all compounds in this class are agents that induce fear and anxiety or suppress motor activity in zebrafish, for example 24H-NBCl (N-(2-Chlorobenzyl)-2,4-dimethoxyphenethylamine) as well as 24H-NBBr (N-(2-bromobenzyl)-2,4-dimethoxyphenethylamine) have been reported to exhibit characteristics of both a hallucinogen and an anxiety-inducing agent.[3] In another study, zebrafish were administered the compound 24H-NBF in vivo for 14 days; a single dose of this compound induced anxiety in the zebrafish, but with chronic exposure, it had the opposite effect, acting as an anxiolytic; it was noted that levels of monoamines, particularly norepinephrine, decreased sharply along with serotonin and dopamine.[5]

References

  1. ↑ 1.0 1.1 Pottie, Eline; Kupriyanova, Olga V.; Brandt, Asher L.; Laprairie, Robert B.; Shevyrin, Vadim A.; Stove, Christophe P. (2021-04-09). "Serotonin 2A Receptor (5-HT2AR) Activation by 25H-NBOMe Positional Isomers: In Vitro Functional Evaluation and Molecular Docking". ACS Pharmacology & Translational Science 4 (2): 479–487. doi:10.1021/acsptsci.0c00189. ISSN 2575-9108. PMID 33860178. 
  2. ↑ 2.0 2.1 Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E. (December 2006). "Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists". Molecular Pharmacology 70 (6): 1956–1964. doi:10.1124/mol.106.028720. ISSN 0026-895X. PMID 17000863. 
  3. ↑ 3.0 3.1 3.2 Demin, Konstantin A.; Kupriyanova, Olga V.; Shevyrin, Vadim A.; Derzhavina, Ksenia A.; Krotova, Nataliya A.; Ilyin, Nikita P.; Kolesnikova, Tatiana O.; Galstyan, David S. et al. (2022-07-06). "Acute behavioral and Neurochemical Effects of Novel N-Benzyl-2-Phenylethylamine Derivatives in Adult Zebrafish". ACS Chemical Neuroscience 13 (13): 1902–1922. doi:10.1021/acschemneuro.2c00123. ISSN 1948-7193. PMID 35671176. http://elar.urfu.ru/handle/10995/131279. 
  4. ↑ 4.0 4.1 Pottie, Eline; Kupriyanova, Olga V.; Shevyrin, Vadim A.; Stove, Christophe P. (2021-05-05). "Synthesis and Functional Characterization of 2-(2,5-Dimethoxyphenyl)-N-(2-fluorobenzyl)ethanamine (25H-NBF) Positional Isomers". ACS Chemical Neuroscience 12 (9): 1667–1673. doi:10.1021/acschemneuro.1c00124. PMID 33906351. https://doi.org/10.1021/acschemneuro.1c00124. 
  5. ↑ Ilyin, Nikita P.; Nabiullin, Arslan D.; Kozlova, Anna D.; Kupriyanova, Olga V.; Shevyrin, Vadim A.; Gloriozova, Tatyana; Filimonov, Dmitry; Lagunin, Alexey et al. (2024-05-15). "Chronic Behavioral and Neurochemical Effects of Four Novel N‑Benzyl-2-phenylethylamine Derivatives Recently Identified as "Psychoactive" in Adult Zebrafish Screens" (in en-US). ACS Chemical Neuroscience 15 (10): 2006–2017. doi:10.1021/acschemneuro.4c00017. ISSN 1948-7193. PMID 38683969. https://www.sciencedirect.com/org/science/article/abs/pii/S1948719324000252. 



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