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25E-NBOH

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
25E-NBOH
Legal status
Legal status
Identifiers
  • 2-({[2-(4-ethyl-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol
CAS Number
PubChemCID
UNII
CompTox Dashboard(EPA)
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

25E-NBOH (2C-E-NBOH,NBOH-2C-E) is a derivative of the phenethylamine derived hallucinogen2C-E. It was first developed by Martin Hansen at theUniversity of Copenhagen in 2010 as a brain imaging agent,[2] but has subsequently been sold as adesigner drug, first being identified in Brazil in 2018 on seized blotter paper,[3][4][5] as well as in Slovenia[6] and France.[7] It acts as a potentserotonin receptoragonist with similar affinity to better-known compounds such as25I-NBOMe at5-HT2A and5-HT2C receptors.[8]

Legal status

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United Kingdom

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This substance is aClass A drug in the United Kingdom as a result of theN-benzylphenethylamine catch-all clause in theMisuse of Drugs Act 1971.[9]

See also

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References

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  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. Retrieved2023-08-27.
  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, et al. (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. ^Pelletier R, Gicquel T, Carvelli J, Balaz P, Pelissier-Alicot AL, Morel I, et al. (May 2024)."Severe 25E-NBOH intoxication associated with MDPHP intake: a case report, metabolism study, and literature review"(PDF).International Journal of Legal Medicine.138 (3):815–822.doi:10.1007/s00414-023-03151-6.PMID 38117418.
  8. ^Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, et al. (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.
  9. ^"The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014".UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
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