24H-NBOMe

24H-NBOMe
Clinical data
Other namesN-(2-Methoxybenzyl)-2,4-dimethoxyphenethylamine; 2,4-DMPEA-NBOMe; 24-NBOMe; 24-NBMeO
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 2-(2,4-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC18H23NO3
Molar mass301.386 g·mol−1
3D model (JSmol)
  • COC1=CC(=C(C=C1)CCNCC2=CC=CC=C2OC)OC
  • InChI=1S/C18H23NO3/c1-20-16-9-8-14(18(12-16)22-3)10-11-19-13-15-6-4-5-7-17(15)21-2/h4-9,12,19H,10-11,13H2,1-3H3
  • Key:CYJMJWILHHQKGL-UHFFFAOYSA-N

24H-NBOMe, also known as N-(2-methoxybenzyl)-2,4-dimethoxyphenethylamine (2,4-DMPEA-NBOMe), is a potent serotonin receptor modulator that is a positional isomer of 25H-NBOMe, in which the methoxy groups are substituted at the 2- and 4-positions of the phenethylamine moiety.[1] This is an N-benzyl derivative of 2,4-dimethoxyphenylethylamine.[1]

Pharmacology

24H-NBOMe is a potent serotonergic agent; primarily, it is a full agonist of the 5-hydroxytryptamine receptor 2A with a Ki value of 1.71–3.88 nM (In mice, this value was 0.68 nM.) 24H-NBOMe binds to the receptor approximately 174 times more strongly than 2,4-DMPEA.[2][3]

24H-NBOMe is a substance that causes anxiety or panic and inhibits motor activity in zebrafish.[4]

History

24H-NBOMe was first described by David Earl Nichols and his colleagues.[2]

See also

References

  1. ^ a b Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  2. ^ a b Braden MR, Parrish JC, Naylor JC, Nichols DE (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. PMID 17000863.
  3. ^ Pottie E, Kupriyanova OV, Brandt AL, Laprairie RB, Shevyrin VA, Stove CP (April 2021). "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. PMC 8033611. PMID 33860178.
  4. ^ Demin KA, Kupriyanova OV, Shevyrin VA, Derzhavina KA, Krotova NA, Ilyin NP, et al. (July 2022). "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. PMID 35671176.
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