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] and France.^[7] It acts as a potent serotonin receptor agonist with similar affinity to better-known compounds such as 25I-NBOMe at 5-HT_2A and 5-HT_2C receptors.^[8]

25E-NBOH

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] DE: NpSG (Industrial and scientific use only) UK: Class A
Identifiers
IUPAC name 2-({[2-(4-ethyl-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol
CAS Number	1391489-79-4 hydrochloride: 1539266-40-4
PubChem CID	135391539
UNII	EB0KU6R3BE
CompTox Dashboard (EPA)	DTXSID001017254
Chemical and physical data
Formula	C19H25NO3
Molar mass	315.413 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC1=CC(=C(C=C1OC)CCNCC2=CC=CC=C2O)OC
InChI 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

Legal status

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.^[9]

See also

• 4-EA-NBOMe
• DOET
• 2C-TFE
• 2C-E-FLY

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, 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". 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.