Chemistry:25C-NBOMe

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Short description: Psychedelic drug
25C-NBOMe
2C-C-NBOMe-skeletal.svg
2C-C-NBOMe-spacefill.png
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC18H22ClNO3
Molar mass335.83 g·mol−1
3D model (JSmol)
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3D-animation of a 25C-NBOMe molecule
Blotter paper containing 25C-NBOMe

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.[2] It acts as a potent agonist of the 5-HT2A receptor,[3] 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).[2][4] 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

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.[5]

Dosage

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.[6]

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.[7] 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.[8]

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.[9]

Effects

Toxicity and harm potential

This section is an excerpt from 25-NB § Toxicity and harm potential[ edit ]

Neurotoxic and cardiotoxic actions

This section is an excerpt from 25-NB § Neurotoxic and cardiotoxic actions[ edit ]

Emergency treatment

This section is an excerpt from 25-NB § Emergency treatment[ edit ]

Drug prohibition laws

Canada

As of October 31, 2016; 25C-NBOMe is a controlled substance (Schedule III) in Canada.[11]

Israel

The NBOMe series of psychoactives became controlled in Israel in May, 2013.[12][13]

New Zealand

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.[14]

Russia

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.[12][15]

Sweden

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.[16]

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.[17]


United States

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.[18] In November 2015, the temporary scheduling was extended for another year.[19]

China

As of October 2015 25C-NBOMe is a controlled substance in China.[20]

Czech Republic

25C-NBOMe is banned in the Czech Republic.[21]

Analogues and derivatives

Analogues and derivatives of 2C-C:

25C-NB*:

Notes

References

  1. ↑ "Substance Details 25C-NBOMe". https://www.unodc.org/LSS/Substance/Details/be41b648-e8e7-4a5b-bec3-51af6c128a9b. 
  2. ↑ 2.0 2.1 "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging 38 (4): 681–693. April 2011. doi:10.1007/s00259-010-1686-8. PMID 21174090. 
  3. ↑ "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience 5 (3): 243–249. March 2014. doi:10.1021/cn400216u. PMID 24397362. 
  4. ↑ 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.
  5. ↑ "25C-NBOMe--new potent hallucinogenic substance identified on the drug market". Forensic Science International 227 (1–3): 7–14. April 2013. doi:10.1016/j.forsciint.2012.08.027. PMID 22989597. 
  6. ↑ "25C-NBOMe short characterisation". Forensic Toxicology 38 (2): 490–495. 2020. doi:10.1007/s11419-020-00530-1. 
  7. ↑ "Multimodal imaging of hallucinogens 25C- and 25I-NBOMe on blotter papers". Drug Testing and Analysis 12 (4): 465–471. April 2020. doi:10.1002/dta.2751. PMID 31846172. 
  8. ↑ 2C-C-NBOMe Dose - erowid
  9. ↑ "[Near fatal intoxication with the novel psychoactive substance 25C-NBOMe]" (in de). Medizinische Klinik, Intensivmedizin und Notfallmedizin 109 (4): 271–275. May 2014. doi:10.1007/s00063-014-0360-5. PMID 24770890. 
  10. ↑ "NBOMes–Highly Potent and Toxic Alternatives of LSD". Frontiers in Neuroscience 14: 78. 26 February 2020. doi:10.3389/fnins.2020.00078. PMID 32174803. 
  11. ↑ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016. https://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.html. 
  12. ↑ 12.0 12.1 "NBOMe Series Legal Status". Erowid. https://www.erowid.org/chemicals/nbome/nbome_law.shtml. 
  13. ↑ "Amendment to Dangerous Drugs Ordinance". 7 June 2013. http://www.health.gov.il/English/Pages/HomePage.aspx. 
  14. ↑ 'Legal high' DIME not so legal. Science Media Centre, March 13th 2012
  15. ↑ "Постановление Правительства Российской Федерации от 6 октября 2011 г. N 822 г. Москва" (in ru). 19 October 2011. http://www.rg.ru/2011/10/19/narko-dok.html. 
  16. ↑ "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika". 24 July 2013. https://lakemedelsverket.se/upload/lvfs/LVFS_2013-15.pdf. 
  17. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014" (in en). http://www.legislation.gov.uk/uksi/2014/1106/made. 
  18. ↑ "Proposed Rules". Drug Enforcement Administration (DEA). 10 October 2013. http://www.gpo.gov/fdsys/pkg/FR-2013-10-10/pdf/2013-24432.pdf. 
  19. ↑ Drug Enforcement Administration (November 2015). "Schedules of Controlled Substances: Extension of Temporary Placement of Three Synthetic Phenethylamines in Schedule I. Final order". Federal Register 80 (219): 70657–70659. PMID 26567439. 
  20. ↑ "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 zh). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  21. ↑ "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (in cs). Ministerstvo zdravotnictví. http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf. 



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