25C-NBOMe

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25C-NBOMe
2C-C-NBOMe-skeletal.svg
2C-C-NBOMe-spacefill.png
Legal status
Legal status
Identifiers
  • 2-(4-Chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H22ClNO3
Molar mass335.83 g·mol−1
3D model (JSmol)
  • COc2ccccc2CNCCc(cc1OC)c(OC)cc1Cl
  • InChI=1S/C18H22ClNO3/c1-21-16-7-5-4-6-14(16)12-20-9-8-13-10-18(23-3)15(19)11-17(13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3 checkY
  • Key:FJFPOGCVVLUYAQ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

25C-NBOMe (NBOMe-2C-C, 2C-C-NBOMe, Cimbi-82) 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.[1] It acts as a potent agonist of the 5HT2A receptor,[2] 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).[1][3] 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.

History[edit]

25C-NBOMe is derived from the psychedelic phenethylamine 2C-C by substitution on the amine with a 2-methoxybenzyl group. 25C-NBOMe is a clumpy white powder with a notably bitter and metallic taste. 25C-NBOMe has been found on blotter mimics sold as LSD.[4]

Dosage[edit]

Blotter paper containing 25C-NBOMe

25C-NBOMe is extremely potent and the effects of the drug increase greatly within a small window of dosage adjustment. Overdose may occur at as little as double an average dose. With inaccurate dosing of street blotter paper, when mistaken for LSD, or when taken as a powder or liquid, this has resulted in multiple accidental deaths.[5]

One study has shown that 25C-NBOMe blotters have 'hotspots' of the drug and the dosage is not evenly applied over the surface of the paper, which could lead to overdose.[6] Sublingually, the threshold for the onset of hallucinogenic effects reportedly is about 100–250 μg, with mild effects at 250–450, strong effects at 450–800, and very strong effects over 800 μg.[7]

NBOMe-substituted compounds have a diminished absorption rate passing through mucus membranes, but generally remain inactive when taken orally. Buccal, sublingual or insufflated routes of administration are all viable options. Absorption rate buccally and sublingually can be increased when complexed with HPBCD complexing sugar, however the most efficient is nasal administration, which shortens the duration while increasing intensity, but has been attributed to several overdoses and deaths.[8]

Effects[edit]

Toxicity and harm potential[edit]

25C-NBOMe overdoses have caused many cases of multi-organ failure and death worldwide.[8][9] NBOMe chemicals, including 25C-NBOMe, frequently cause tachycardia (rapid heart rate), hypertension (high blood pressure), and vasoconstriction (which reduces blood flow). These physical symptoms can cause significant risks to health, especially when the user has underlying health issues or has taken a combination of drugs.[10] 25C-NBOMe is significantly more dangerous and potent than LSD, which is not easily overdosed.

25C-NBOme is a substituted para-Chloroamphetamine which is a known neurotoxin. 25C-NBOMe being much more potent and a direct serotonergic neurotoxic agent.[citation needed]

25C-NBOme has been shown in preliminary studies to be toxic to development, heart health and brain health in zebrafish, rats, and brine shrimp (common model organisms for studying potential drug effects on humans), but more research is needed on this topic, the dosages, and if this applies to humans. The authors of one study recommended further research on if the drug is potentially damaging to pregnant women and their fetuses due to the potentially damaging effects to development.[11][12]

While most deaths are due to the physical effects of the drug, one person died after repeatedly running into walls while under the effects of 25C-NBOMe, 25B-NBOMe and MDMA; this person had thought the NBOMe drugs they had taken were LSD.[10][13] Another died while drowning while under the effects of 25C-NBOMe and 25H-NBOMe, shortly after expressing they wished to commit suicide.[14]

Drug prohibition laws[edit]

Canada[edit]

As of October 31, 2016; 25C-NBOMe is a controlled substance (Schedule III) in Canada. http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php

Israel[edit]

The NBOMe series of psychoactives became controlled in Israel in May, 2013.[15][16]

New Zealand[edit]

25C-NBOMe was sold as a designer drug in New Zealand in early 2012, but was withdrawn from sale after a statement by Associate Health Minister Peter Dunne that 25C-NBOMe would be considered to be substantially similar in chemical structure to the illegal hallucinogen DOB, and was therefore a Class C controlled drug analogue.[17]

Russia[edit]

Russia became the first country to regulate the NBOME class. The entire NBOMe series of psychoactives became controlled in the Russian Federation starting October, 2011.[15][18]

Sweden[edit]

Sveriges riksdag added 25C-NBOMe to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of Aug 1, 2013, published by Medical Products Agency in their regulation LVFS 2013:15 listed as 25C-NBOMe 2-(4-kloro-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.[19]

United Kingdom[edit]

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.[20]


United States[edit]

Several NBOMe series compounds will be temporarily scheduled in the United States for 2 years. The temporary scheduling applies to 25C-NBOMe, 25B-NBOMe, and 25I-NBOMe.[21] In November 2015, the temporary scheduling was extended for another year.[22]

China[edit]

As of October 2015 25C-NBOMe is a controlled substance in China.[23]

Czech Republic[edit]

25C-NBOMe is banned in the Czech Republic.[24]

Analogues and derivatives[edit]

References[edit]

  1. ^ a b Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J.; et al. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–93. doi:10.1007/s00259-010-1686-8. PMID 21174090. S2CID 12467684.
  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. ^ Zuba, D.; Sekuła, K.; Buczek, A. (2013). "25C-NBOMe – New potent hallucinogenic substance identified on the drug market". Forensic Science International. 227 (1–3): 7–14. doi:10.1016/j.forsciint.2012.08.027. PMID 22989597.
  5. ^ Kamińska, Katarzyna; Świt, Paweł; Malek, Kamilla (2020). "25C-NBOMe short characterisation". Forensic Toxicology.
  6. ^ Lützen, Elias; Holtkamp, Michael; Stamme, Imke; Schmid, Robin; Sperling, Michael; Pütz, Michael; Karst, Uwe (April 2020). "Multimodal imaging of hallucinogens 25C‐ and 25I‐NBOMe on blotter papers". Drug Testing and Analysis. 12 (4): 465–471. doi:10.1002/dta.2751. ISSN 1942-7603.
  7. ^ 2C-C-NBOMe Dose - erowid
  8. ^ a b S. Grautoff; J. Kähler (May 2014). "Lebensgefährliche Intoxikation mit der neuen psychoaktiven Substanz 25C-NBOMe". Medizinische Klinik - Intensivmedizin und Notfallmedizin (in German). 109 (4): 271–275. doi:10.1007/s00063-014-0360-5. PMID 24770890.
  9. ^ Tarpgaard M, Mærkedahl R, Lauridsen KB (August 2015). "Fatalt forløb efter intoksikation med det nye designerdrug 25C-NBOMe". Ugeskrift for Laeger (in Danish). 177 (35). PMID 26324189.
  10. ^ a b Lipow, Matthew; Kaleem, Syed; Espiridion, Eduardo (2022-03-30). "NBOMe Toxicity and Fatalities: A Review of the Literature". Transformative Medicine (T-Med). 1 (1): 12–18. doi:10.54299/tmed/msot8578. ISSN 2831-8978.
  11. ^ Xu, Peng; Qiu, Qiyang; Li, Haijie; Yan, Sicheng; Yang, Mengxiang; Naman, C. Benjamin; Wang, Youmei; Zhou, Wenhua; Shen, Haowei; Cui, Wei (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. ISSN 1029-8428.
  12. ^ Álvarez-Alarcón, Natalie; Osorio-Méndez, Jhon Jairo; Ayala-Fajardo, Adis; Garzón-Méndez, William F.; Garavito-Aguilar, Zayra V. (2021-01-01). "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.
  13. ^ Byard, Roger W.; Cox, Matthew; Stockham, Peter (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.
  14. ^ Morini, Luca; Bernini, Marzia; Vezzoli, Sara; Restori, Mario; Moretti, Matteo; Crenna, Stefano; Papa, Pietro; Locatelli, Carlo; Osculati, Antonio Marco Maria; Vignali, Claudia; Groppi, Angelo (2017-10-01). "Death after 25C-NBOMe and 25H-NBOMe consumption". Forensic Science International. 279: e1–e6. doi:10.1016/j.forsciint.2017.08.028. ISSN 0379-0738.
  15. ^ a b "NBOMe Series Legal Status". Erowid. Retrieved 5 September 2015.
  16. ^ "Amendment to Dangerous Drugs Ordinance". Israeli Ministry of Health. 7 June 2013. Retrieved 11 September 2015.
  17. ^ 'Legal high' DIME not so legal. Science Media Centre, March 13th 2012
  18. ^ "Постановление Правительства Российской Федерации от 6 октября 2011 г. N 822 г. Москва" (in Russian). 19 October 2011. Retrieved 5 September 2015.
  19. ^ Generaldirektör Ch ristina Rångemark Åkerman (24 July 2013). "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" (PDF). Retrieved 5 September 2015.
  20. ^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
  21. ^ Thomas M. Harrigan (10 October 2013). "Proposed Rules" (PDF). Drug Enforcement Administration (DEA). Retrieved 5 September 2015.
  22. ^ Drug Enforcement Administration (2015). "Schedules of Controlled Substances: Extension of Temporary Placement of Three Synthetic Phenethylamines in Schedule I. Final order". Fed. Regist. 80 (219): 70657–9. PMID 26567439.
  23. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  24. ^ "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF) (in Czech). Ministerstvo zdravotnictví.