25C-NBOMe

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25C-NBOMe
Legal status
Legal status
Identifiers
  • 2-(4-Chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
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.[3] It acts as a potent agonist of the 5-HT2A receptor,[4] 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).[3][5] 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.[6]

Dosage

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.[7]

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.[8] 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.[9]

NBOMe-substituted compounds have a diminished absorption rate passing through mucous 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.[10]

Effects

Toxicity and harm potential

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Neurotoxic and cardiotoxic actions

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Emergency treatment

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Drug prohibition laws

Canada

As of October 31, 2016; 25C-NBOMe is a controlled substance (Schedule III) in Canada.[12]

Israel

The NBOMe series of psychoactives became controlled in Israel in May, 2013.[13][14]

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.[15]

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.[13][16]

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.[17]

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.[18]

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.[19] In November 2015, the temporary scheduling was extended for another year.[20]

China

As of October 2015 25C-NBOMe is a controlled substance in China.[21]

Czech Republic

25C-NBOMe is banned in the Czech Republic.[22]

Analogues and derivatives

Analogues and derivatives of 2C-C:

25C-NB*:

N-(2C)-fentanyl:

Notes

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 português do Brasil). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ "Substance Details 25C-NBOMe". Retrieved 2024-01-23.
  3. ^ 3.0 3.1 Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, et al. (April 2011). "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. doi:10.1007/s00259-010-1686-8. PMID 21174090. S2CID 12467684.
  4. ^ Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (March 2014). "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience. 5 (3): 243–249. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.
  5. ^ 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.
  6. ^ Zuba D, Sekuła K, Buczek A (April 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.
  7. ^ Kamińska K, Świt P, Malek K (2020). "25C-NBOMe short characterisation". Forensic Toxicology. 38 (2): 490–495. doi:10.1007/s11419-020-00530-1. S2CID 214704393.
  8. ^ Lützen E, Holtkamp M, Stamme I, Schmid R, Sperling M, Pütz M, Karst U (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. PMID 31846172. S2CID 209388281.
  9. ^ 2C-C-NBOMe Dose - erowid
  10. ^ Grautoff S, Kähler J (May 2014). "[Near fatal intoxication with the novel psychoactive substance 25C-NBOMe]". Medizinische Klinik, Intensivmedizin und Notfallmedizin (in Deutsch). 109 (4): 271–275. doi:10.1007/s00063-014-0360-5. PMID 24770890.
  11. ^ 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.
  12. ^ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Government of Canada. 4 May 2016. Archived from the original on 5 August 2022. Retrieved 6 May 2023.
  13. ^ 13.0 13.1 "NBOMe Series Legal Status". Erowid. Retrieved 5 September 2015.
  14. ^ "Amendment to Dangerous Drugs Ordinance". Israeli Ministry of Health. 7 June 2013. Retrieved 11 September 2015.
  15. ^ 'Legal high' DIME not so legal. Science Media Centre, March 13th 2012
  16. ^ "Постановление Правительства Российской Федерации от 6 октября 2011 г. N 822 г. Москва" (in русский). 19 October 2011. Retrieved 5 September 2015.
  17. ^ Åkerman CR (24 July 2013). "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" (PDF). Retrieved 5 September 2015.
  18. ^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
  19. ^ Harrigan TM (10 October 2013). "Proposed Rules" (PDF). Drug Enforcement Administration (DEA). Retrieved 5 September 2015.
  20. ^ 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.
  21. ^ "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 中文). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  22. ^ "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF) (in čeština). Ministerstvo zdravotnictví. Archived from the original (PDF) on 2016-03-09. Retrieved 2016-02-06.
  23. ^ "Explore N-(2C-C)-Fentanyl | PiHKAL · info". isomerdesign.com.
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