Potency and safety analysis of hemp-derived delta-9 products: The hemp vs. cannabis demarcation problem

25E-NBOH
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); 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;

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]

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]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ Analytical Report. 25E-NBOH. Nacionalni Forenzični Laboratorij, Slovenia, 24 January 2018
^ 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.
^ 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.
^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.

[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.

[pmid32086005-5] 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

[pmid38117418-7] 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.

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Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

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

Potency and safety analysis of hemp-derived delta-9 products: The hemp vs. cannabis demarcation problem

Legal status

United Kingdom

See also

References