25E-NBOH

25E-NBOH (2C-E-NBOH, NBOH-2C-E) is a derivative of the phenethylamine derived hallucinogen 2C-E. It was first developed by Martin Hansen at the University of Copenhagen in 2010 as a brain imaging agent,[2] but has subsequently been sold as a designer drug, first being identified in Brazil in 2018 on seized blotter paper,[3][4][5] as well as in Slovenia.[6] It acts as a potent serotonin receptor agonist with similar affinity to better-known compounds such as 25I-NBOMe at 5-HT2A and 5-HT2C receptors.[7]

25E-NBOH
Legal status
Legal status
Identifiers
  • 2-({[2-(4-ethyl-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol
CAS Number
PubChem CID
UNII
Chemical and physical data
FormulaC19H25NO3
Molar mass315.413 g·mol−1
3D model (JSmol)
  • CCC1=CC(=C(C=C1OC)CCNCC2=CC=CC=C2O)OC
  • InChI=1S/C19H25NO3/c1-4-14-11-19(23-3)15(12-18(14)22-2)9-10-20-13-16-7-5-6-8-17(16)21/h5-8,11-12,20-21H,4,9-10,13H2,1-3H3
  • Key:SYBINTRPEZWFLZ-UHFFFAOYSA-N

United Kingdom

This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.[8]

See also

References
  1. Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. Hansen M (2010-12-16). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (Ph.D. thesis). University of Copenhagen. doi:10.13140/RG.2.2.33671.14245.
  3. Machado Y, Neto JC, Lordeiro RA, Silva MF, Piccin E (January 2019). "Profile of new psychoactive substances (NPS) and other synthetic drugs in seized materials analysed in a Brazilian forensic laboratory". Forensic Toxicology. 37 (1): 265–71. doi:10.1007/s11419-018-0456-3. S2CID 53812909.
  4. Machado Y, Neto JC, Lordeiro RA, Alves RB, Piccin E (January 2020). "Identification of new NBOH drugs in seized blotter papers: 25B-NBOH, 25C-NBOH, and 25E-NBOH". Forensic Toxicology. 38 (1): 203–15. doi:10.1007/s11419-019-00509-7. S2CID 209672508.
  5. Rodrigues de Morais D, Francisco da Cunha K, Betoni Rodrigues T, Lanaro R, de Melo Barbosa L, Jardim Zacca J, Nogueira Eberlin M, Costa JL (April 2020). "Triple quadrupole-mass spectrometry protocols for the analysis of NBOMes and NBOHs in blotter papers". Forensic Science International. 309: 110184. doi:10.1016/j.forsciint.2020.110184. PMID 32086005. S2CID 211246833.
  6. Analytical Report. 25E-NBOH. Nacionalni Forenzični Laboratorij, Slovenia, 24 January 2018
  7. Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (March 2014). "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience. 5 (3): 243–9. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.
  8. "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
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