25E-NBOH

Last updated

25E-NBOH
25E-NBOH structure.png
Legal status
Legal status
Identifiers
  • 2-({[2-(4-ethyl-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol
CAS Number
PubChem CID
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C19H25NO3
Molar mass 315.413 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 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-HT2A and 5-HT2C receptors. [8]

Contents

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

Related Research Articles

<span class="mw-page-title-main">25I-NBOH</span> Chemical compound

25I-NBOH is a derivative of the phenethylamine-derived hallucinogen 2C-I that was discovered in 2006 by a team at Purdue University.

<span class="mw-page-title-main">25I-NBOMe</span> Synthetic hallucinogen

25I-NBOMe, also known as Smiles, or N-Bomb, is a novel synthetic psychoactive substance with strong hallucinogenic properties, synthesized in 2003 for research purposes. Since 2010, it has circulated in the recreational drug scene, often misrepresented as LSD.

<span class="mw-page-title-main">25B-NBOMe</span> Chemical compound

25B-NBOMe is a derivative of the phenethylamine psychedelic 2C-B, discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent full agonist for the 5HT2A receptor. Duration of effects lasts about 3–10 hours, although the parent compound is rapidly cleared from the blood when used in the radiolabeled form in tracer doses. Recently, Custodio et al. (2019) evaluated the potential involvement of dysregulated dopaminergic system, neuroadaptation, and brain wave changes which may contribute to the rewarding and reinforcing properties of 25B-NBOMe in rodents.

<span class="mw-page-title-main">25I-NBF</span> Chemical compound

25I-NBF is a derivative of the phenethylamine hallucinogen 2C-I, which acts as a highly potent partial agonist for the human 5-HT2A receptor, with bias towards the β-arrestin 2 coupled signalling pathway. It has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET).

<span class="mw-page-title-main">25TFM-NBOMe</span> Chemical compound

25TFM-NBOMe is a derivative of the phenethylamine hallucinogen 2C-TFM, discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent partial agonist for the 5-HT2A receptor, though its relative potency is disputed, with some studies finding it to be of lower potency than 25I-NBOMe, while others show it to be of similar or higher potency, possibly because of differences in the assay used. 2C-TFM-NB2OMe can be taken to produce psychedelic effects similar to 2C-I-NB2OMe and 2C-D-NB2OMe.

<span class="mw-page-title-main">25C-NBOMe</span> Psychedelic drug

25C-NBOMe is a psychedelic drug and derivative of the psychedelic phenethylamine 2C-C. 25C-NBOMe appeared on online vendor sites in 2010 but was not reported in the literature until 2011. It acts as a potent agonist of the 5-HT2A receptor, and has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET). Multiple deaths have occurred from usage of 25C-NBOMe due to the ease of accidental overdose. The long-term toxic effects of the drug have not been researched.

<span class="mw-page-title-main">25D-NBOMe</span> Chemical compound

25D-NBOMe is a derivative of the phenethylamine derived hallucinogen 2C-D. It acts in a similar manner to related compounds such as 25I-NBOMe, which is a potent agonist at the 5-HT2A receptor. 25D-NBOMe has been sold as a street drug since 2010 and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe. It was banned as a Temporary Class Drug in the UK on 10 June 2013 after concerns about its recreational use.

<span class="mw-page-title-main">25C-NBOH</span> Chemical compound

25-C-NBOH is a derivative of the phenethylamine derived hallucinogen 2C-C which has been sold as a designer drug. It has similar serotonin receptor affinity to the better-known compound 25C-NBOMe.

<span class="mw-page-title-main">25CN-NBOMe</span> Chemical compound

25CN-NBOMe is a derivative of the phenethylamine 2C-CN. It acts in a similar manner to related compounds such as 25I-NBOMe, which are potent agonists at the 5HT2A receptor.

<span class="mw-page-title-main">25N-NBOMe</span> Chemical compound

25N-NBOMe is a derivative of the hallucinogen 2C-N. The pharmacological properties of 25N-NBOMe have not been described in the scientific literature, but it is believed to act in a similar manner to related compounds such as 25I-NBOMe and 25C-NBOMe, which are potent agonists at the 5HT2A receptor. 25N-NBOMe has been sold as a street drug and has only been described in the literature in terms of identification by forensic analysis.

<span class="mw-page-title-main">25E-NBOMe</span> Chemical compound

25E-NBOMe is a derivative of the phenethylamine 2C-E. It acts in a similar manner to related compounds such as 25I-NBOMe, which are potent agonists at the 5-HT2A receptor. 25E-NBOMe has been sold as a drug and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe.

<span class="mw-page-title-main">25P-NBOMe</span> Chemical compound

25P-NBOMe is a derivative of the phenethylamine 2C-P. It acts in a similar manner to related compounds such as 25I-NBOMe, which are potent agonists at the 5-HT2A receptor. 25P-NBOMe has been sold as a drug and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe.

<span class="mw-page-title-main">25B-NBOH</span> Chemical compound

25B-NBOH is a derivative of the phenethylamine derived hallucinogen 2C-B which has been sold as a designer drug. It acts as a potent serotonin receptor agonist with similar affinity to the better-known compound 25B-NBOMe at 5-HT2A and 5-HT2C receptors with pKis values of 8.3 and 9.4, respectively.

<span class="mw-page-title-main">25I-NB34MD</span> Derivative of the phenethylamine hallucinogen 2C-I

25I-NB34MD (NB34MD-2C-I) is a derivative of the phenethylamine hallucinogen 2C-I, which acts as a potent partial agonist for the human 5-HT2A receptor, and presumably has similar properties to 2C-I. It has a binding affinity of 0.67nM at the human 5-HT2A receptor, making it several times weaker than its positional isomer 25I-NBMD and a similar potency to 25I-NBF.

<span class="mw-page-title-main">25C-NBF</span> Chemical compound

25C-NBF is a derivative of the phenethylamine hallucinogen 2C-C, which acts as a highly potent partial agonist for the human 5-HT2A receptor.

<span class="mw-page-title-main">25G-NBOMe</span> Chemical compound

25G-NBOMe (NBOMe-2C-G) is a derivative of the phenethylamine hallucinogen 2C-G, which acts as a highly potent agonist for the human 5-HT2A receptor.

<span class="mw-page-title-main">25H-NBOMe</span> Chemical compound

25H-NBOMe (NBOMe-2C-H) is a derivative of the phenethylamine hallucinogen 2C-H, which acts as a highly potent full agonist for the human 5-HT2A receptor.

<span class="mw-page-title-main">25iP-NBOMe</span> Chemical compound

25iP-NBOMe is a derivative of the phenethylamine hallucinogen 2C-iP, which acts as a highly potent agonist for the human 5-HT2A receptor.

<span class="mw-page-title-main">25-NB</span> Family of serotonergic psychedelics

The 25-NB (25x-NBx) series, sometimes alternatively referred to as the NBOMe compounds, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. They act as selective agonists of the serotonin 5-HT2A receptor. The 25-NB family is unique relative to other classes of psychedelics in that they are, generally speaking, extremely potent and relatively selective for the 5-HT2A receptor. Use of NBOMe series drugs has caused many deaths and hospitalisations since the drugs popularisation in the 2010s. This is primarily due to their high potency, unpredictable pharmacokinetics, and sellers passing off the compounds in the series as LSD.

<span class="mw-page-title-main">25T7-NBOMe</span> Chemical compound

25T7-NBOMe is a substituted phenethylamine derivative from the 25-NB family. It acts as an agonist at the 5-HT2A and 5-HT2C serotonin receptors, has psychedelic effects and has been sold as a designer drug.

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.