25N-NBOMe

Leave a Comment / NBxx / By

Summary

25N-NBOMe (2C-N-NBOMe, NBOMe-2C-N) represents a derivative of the hallucinogenic compound 2C-N. Although the scientific literature has not extensively explored the pharmacological properties 25N-NBOMe, it is believed to operate similarly to its related counterparts, such as 25I-NBOMe and 25C-NBOMe. These related compounds are recognized as potent agonists at the 5HT2A receptor. Notably, 25N-NBOMe has been circulated as a street drug and has solely been documented in terms of identification through forensic analysis.

Identifiers
CAS Number1354632-03-3
3D model (JSmol)Interactive image
ChemSpider52085577
PubChemCID118536028
UNII0G7SSW2N0S 
CompTox Dashboard(EPA)DTXSID501014186

Toxicity

NBOMe substances are commonly associated with severe and life-threatening toxicity, often leading to fatal consequences. Extensive studies on the NBOMe family of compounds have revealed their potential neurotoxic and cardiotoxic effects. Individuals exposed to NBOMe compounds frequently exhibit symptoms of autonomic dysfunction, including vasoconstriction, hypertension, tachycardia, and hallucinations. Additionally, the toxidrome associated with NBOMe intake encompasses a range of alarming symptoms, such as agitation, seizures, hyperthermia, and hypertonia, sometimes culminating in fatalities. Researchers have noted that NBOMe intoxication often manifests signs of serotonin syndrome, with a higher propensity for inducing seizures than other psychedelics.
NBOMe and NBOHs are frequently passed off as LSD and distributed on blotter papers, characterized by a bitter taste and distinct safety profiles. Despite their high potency, recreational doses of LSD have exhibited minimal instances of acute toxicity. Tragic fatalities related to NBOMe ingestion suggest that many individuals unknowingly consumed the substance, mistaking it for LSD. Researchers have warned that individuals familiar with LSD may mistakenly assume a false sense of security when ingesting NBOMe. While most fatalities are attributed to the physical effects of the drug, there have been reports of deaths resulting from self-harm and suicide under the influence of the substance.
Due to limited documentation of NBOMe consumption, the long-term effects of the substance remain largely unknown. Notably, NBOMe compounds are not active when taken orally. They are typically administered sublingually [19]: 3 . Users often experience numbness of the tongue and mouth, followed by a distinct metallic chemical taste, which researchers consider a crucial distinguishing factor between NBOMe compounds and LSD.
Neurotoxic and cardiotoxic actions of NBOMe compounds primarily stem from their potent agonist activity at various 5-HT receptors. Prolonged activation of 5-HT2B has been linked to the development of cardiac valvulopathy, implicating these compounds in drug-induced valvular heart disease. The high affinity of NBOMe compounds for adrenergic α1 receptors contributes to their stimulant-like cardiovascular effects.
In vitro studies have demonstrated the cytotoxicity of 25C-NBOMe on various neuronal cell lines and cardiomyocytes, revealing its potential for damaging brain and heart health. Additionally, 25C-NBOMe, along with its derivative 25D-NBOMe, has shown adverse effects on the development of zebrafish, rats, and Artemia salina, underscoring the need for further research on its implications for human health and development.
Without specific antidotes for NBOMes, acute intoxication is managed through symptomatic treatments, including benzodiazepines, antipsychotic drugs, and antiarrhythmic agents such as beta blockers. Specific interventions are also employed to address rhabdomyolysis, which can lead to critical complications like metabolic acidosis and acute kidney injury.

Legality

United States: 25N-NBOMe is prohibited in Alabama, making its possession and use illegal.

Hungary: In Hungary, 25N-NBOMe is also classified as illegal, and its sale, possession, and consumption are forbidden by law.

Sweden: The Riksdag in Sweden included 25N-NBOMe in the Narcotic Drugs Punishments Act, categorizing it under Swedish Schedule I. This places it among substances, plant materials, and fungi without recognized medical usage. The regulation, outlined in LVFS 2014:11 by the Medical Products Agency (MPA), officially designates 25N-NBOMe as 2-(2,5-dimethoxy-4-nitrophenyl)-N-(2-methoxybenzyl)ethanamine.

United Kingdom: Within the United Kingdom, 25N-NBOMe is classified as a Class A drug due to the N-benzyl phenethylamine catch-all provision within the Misuse of Drugs Act of 1971, making its possession, sale, and use illegal under British law.

FAQ

1. What is 25N-NBOMe?

25N-NBOMe, also known as 2C-N-NBOMe or NBOMe-2C-N, is a derivative of the hallucinogenic substance 2C-N. It’s part of a group of synthetic drugs known for their psychedelic effects, acting as potent agonists at the 5HT2A receptor.

2. How does 25N-NBOMe affect the body?

While the specific pharmacological properties of 25N-NBOMe haven’t been extensively documented in scientific literature, it’s believed to have similar effects to related compounds like 25I-NBOMe and 25C-NBOMe. These substances are known to be potent agonists at the 5HT2A receptor, leading to hallucinogenic experiences.

3. Is 25N-NBOMe safe for use?

The safety of 25N-NBOMe is uncertain. It is often associated with life-threatening toxicity and adverse effects, including neurotoxicity and cardiotoxicity. Its use can lead to severe health issues and, in some cases, fatalities.

4. How is 25N-NBOMe typically consumed?

25N-NBOMe is typically sold as a street drug, used by ingesting or smoking. However, it is crucial to note that the consumption of this substance is associated with significant risks, and its legality varies by country.

5. Is 25N-NBOMe legal?

The legal status of 25N-NBOMe varies by country. It is categorized as an illegal substance in some places, while in others, it may not be explicitly regulated. Always check your local laws and regulations to understand the legal status in your area.

6. Are there any known health risks associated with 25N-NBOMe?

25N-NBOMe is often linked to severe health risks, including life-threatening toxicity, neurotoxicity, and cardiotoxicity. Consumption can result in symptoms like vasoconstriction, hypertension, tachycardia, hallucinations, agitation, seizure, hyperthermia, and more.

7. Can 25N-NBOMe be confused with other substances?

Yes, it has been reported that NBOMe compounds are sometimes sold as other drugs like LSD, especially on blotter paper. Users may believe they are taking one substance but unknowingly consume 25N-NBOMe, which can be dangerous due to its unpredictability and potency.

8. What are the long-term effects of 25N-NBOMe use?

Due to limited documentation, the long-term effects of 25N-NBOMe still need to be discovered. It’s essential to understand that the potential risks and consequences of its use may need to be fully comprehended.

9. How is 25N-NBOMe different from LSD?

While 25N-NBOMe and LSD are hallucinogenic substances, they have different safety profiles and effects. 25N-NBOMe is known for its high potency and increased risks, while recreational doses of LSD have generally resulted in fewer cases of acute toxicity.

10. What should I do if I suspect someone has consumed 25N-NBOMe and is experiencing adverse effects?

If you suspect someone has ingested 25N-NBOMe and is displaying adverse effects or symptoms, seeking immediate medical attention is crucial. There are no specific antidotes for NBOMe compounds, so treatment addresses symptoms and complications to ensure the person’s safety.

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.; Phonekeo, K.; Paine, J. S.; Leth-Petersen, S.; Begtrup, M.; Bräuner-Osborne, H.; Kristensen, J. L. (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.
  3. 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.
  4. Casale, John F.; Hays, Patrick A. (2012). “Characterization of Eleven 2,5-Dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) Derivatives and Differentiation from their 3- and 4-Methoxybenzyl Analogues – Part I” (PDF). Microgram Journal. 9 (2): 84–109. Retrieved 14 January 2014.
  5. Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014). “Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products”. Forensic Toxicology. 32 (1): 105–115. doi:10.1007/s11419-013-0217-2. S2CID 32599561.
  6. Sean I, Joe R, Jennifer S, and Shaun G (28 March 2022). “A cluster of 25B-NBOH poisonings following exposure to powder sold as lysergic acid diethylamide (LSD)”. Clinical Toxicology. 60 (8): 966–969. doi:10.1080/15563650.2022.2053150. PMID 35343858. S2CID 247764056.
  7. Amy E, Katherine W, John R, Sonyoung K, Robert J, Aaron J (December 2018). “Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors”. Biochemical Pharmacology. 158: 27–34. doi:10.1016/j.bcp.2018.09.024. PMC 6298744. PMID 30261175.
  8. Jolanta Z, Monika K, and Piotr A (26 February 2020). “NBOMes–Highly Potent and Toxic Alternatives of LSD”. Frontiers in Neuroscience. 14: 78. doi:10.3389/fnins.2020.00078. PMC 7054380. PMID 32174803.
  9. Lipow M, Kaleem SZ, Espiridion E (30 March 2022). “NBOMe Toxicity and Fatalities: A Review of the Literature”. Transformative Medicine. 1 (1): 12–18. doi:10.54299/tmed/msot8578. ISSN 2831-8978. S2CID 247888583.
  10. Micaela T, Sabrine B, Raffaella A, Giorgia C, Beatrice M, Tatiana B, Federica B, Giovanni S, Francesco B, Fabio G, Krystyna G, Matteo M (21 April 2022). “Effect of -NBOMe Compounds on Sensorimotor, Motor, and Prepulse Inhibition Responses in Mice in Comparison With the 2C Analogs and Lysergic Acid Diethylamide: From Preclinical Evidence to Forensic Implication in Driving Under the Influence of Drugs”. Front Psychiatry. 13: 875722. doi:10.3389/fpsyt.2022.875722. PMC 9069068. PMID 35530025.
  11. Cristina M, Matteo M, Nicholas P, Maria C, Micaela T, Raffaella A, Maria L (12 December 2019). “Neurochemical and Behavioral Profiling in Male and Female Rats of the Psychedelic Agent 25I-NBOMe”. Frontiers in Pharmacology. 10: 1406. doi:10.3389/fphar.2019.01406. PMC 6921684. PMID 31915427.
  12. Anna R, Dino L, Julia R, Daniele B, Marius H, Matthias L (December 2015). “Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)”. Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. S2CID 10382311.
  13. David W, Roumen S, Andrew C, Paul D (6 February 2015). “Prevalence of use and acute toxicity associated with the use of NBOMe drugs”. Clinical Toxicology. 53 (2): 85–92. doi:10.3109/15563650.2015.1004179. PMID 25658166. S2CID 25752763.
  14. Humston C, Miketic R, Moon K, Ma P, Tobias J (2017-06-05). “Toxic Leukoencephalopathy in a Teenager Caused by the Recreational Ingestion of 25I-NBOMe: A Case Report and Review of Literature”. Journal of Medical Cases. 8 (6): 174–179. doi:10.14740/jmc2811w. ISSN 1923-4163.
  15. Justin P, Stephen R, Kylin A, Alphonse P, Michelle P (2015). “Analysis of 25I-NBOMe, 25B-NBOMe, 25C-NBOMe and Other Dimethoxyphenyl-N-[(2-Methoxyphenyl) Methyl]Ethanamine Derivatives on Blotter Paper”. Journal of Analytical Toxicology. 39 (8): 617–623. doi:10.1093/jat/bkv073. PMC 4570937. PMID 26378135.
  16. Morini L, Bernini M, Vezzoli S, Restori M, Moretti M, Crenna S, et al. (October 2017). “Death after 25C-NBOMe and 25H-NBOMe consumption”. Forensic Science International. 279: e1–e6. doi:10.1016/j.forsciint.2017.08.028. PMID 28893436.
  17. Byard RW, Cox M, Stockham P (November 2016). “Blunt Craniofacial Trauma as a Manifestation of Excited Delirium Caused by New Psychoactive Substances”. Journal of Forensic Sciences. 61 (6): 1546–1548. doi:10.1111/1556-4029.13212. PMID 27723094. S2CID 4734566.
  18. Sabastian LP, Christoffer B, Martin H, Martin AC, Jan K, Jesper LK (14 February 2014). “Correlating the Metabolic Stability of Psychedelic 5-HT2A Agonists with Anecdotal Reports of Human Oral Bioavailability”. Neurochemical Research. 39 (10): 2018–2023. doi:10.1007/s11064-014-1253-y. PMID 24519542. S2CID 254857910.
  19. Adam H (18 January 2017). “Pharmacology and Toxicology of N-Benzylphenethylamine (“NBOMe”) Hallucinogens”. Neuropharmacology of New Psychoactive Substances. Current Topics in Behavioral Neurosciences. Vol. 32. Springer. pp. 283–311. doi:10.1007/7854_2016_64. ISBN 978-3-319-52444-3. PMID 28097528.
  20. Boris D, Cristian C, Marcelo K, Edwar F, Bruce KC (August 2016). “Analysis of 25 C NBOMe in Seized Blotters by HPTLC and GC–MS”. Journal of Chromatographic Science. 54 (7): 1153–1158. doi:10.1093/chromsci/bmw095. PMC 4941995. PMID 27406128.
  21. Francesco SB, Ornella C, Gabriella A, Giuseppe V, Rita S, Flaminia BP, Eduardo C, Pierluigi S, Giovanni M, Guiseppe B, Fabrizio S (3 July 2014). “25C-NBOMe: preliminary data on pharmacology, psychoactive effects, and toxicity of a new potent and dangerous hallucinogenic drug”. BioMed Research International. 2014: 734749. doi:10.1155/2014/734749. PMC 4106087. PMID 25105138.
  22. Adam JP, Simon HT, Simon LH (September 2021). “Pharmacology and toxicology of N-Benzyl-phenylethylamines (25X-NBOMe) hallucinogens”. Novel Psychoactive Substances: Classification, Pharmacology and Toxicology (2 ed.). Academic Press. pp. 279–300. doi:10.1016/B978-0-12-818788-3.00008-5. ISBN 978-0-12-818788-3. S2CID 240583877.
  23. Rothman RB, Baumann MH, Savage JE, Rauser L, McBride A, Hufeisen SJ, Roth BL (Dec 2000). “Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications”. Circulation. 102 (23): 2836–41. doi:10.1161/01.CIR.102.23.2836. PMID 11104741.
  24. Fitzgerald LW, Burn TC, Brown BS, Patterson JP, Corjay MH, Valentine PA, Sun JH, Link JR, Abbaszade I, Hollis JM, Largent BL, Hartig PR, Hollis GF, Meunier PC, Robichaud AJ, Robertson DW (Jan 2000). “Possible role of valvular serotonin 5-HT(2B) receptors in the cardiopathy associated with fenfluramine”. Molecular Pharmacology. 57 (1): 75–81. PMID 10617681.
  25. Roth BL (Jan 2007). “Drugs and valvular heart disease”. The New England Journal of Medicine. 356 (1): 6–9. doi:10.1056/NEJMp068265. PMID 17202450.
  26. Xu P, Qiu Q, Li H, Yan S, Yang M, Naman CB, et al. (26 February 2019). “25C-NBOMe, a Novel Designer Psychedelic, Induces Neurotoxicity 50 Times More Potent Than Methamphetamine In Vitro”. Neurotoxicity Research. 35 (4): 993–998. doi:10.1007/s12640-019-0012-x. PMID 30806983. S2CID 255763701.
  27. Álvarez-Alarcón N, Osorio-Méndez JJ, Ayala-Fajardo A, Garzón-Méndez WF, Garavito-Aguilar ZV (2021). “Zebrafish and Artemia salina in vivo evaluation of the recreational 25C-NBOMe drug demonstrates its high toxicity”. Toxicology Reports. 8: 315–323. doi:10.1016/j.toxrep.2021.01.010. ISSN 2214-7500. PMC 7868744. PMID 33598409.
  28. Alabama Senate Bill SB 333: Controlled Substances
  29. A Daath.hu kiegészítése a BSZKI “designer jogi listáján” nem szereplő, de az UP jegyzék 1.-4. szerkezeti leírásainak megfelelő, illetve az 5. felsorolásában szereplő néhány anyagról
  30. “Archived copy” (PDF). Archived from the original (PDF) on 2015-03-16. Retrieved 2017-04-21.
  31. “The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014”. www.legislation.gov.uk.

Leave a Comment

Your email address will not be published. Required fields are marked *