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
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)
3D-animation of a 25C-NBOMe molecule
Blotter paper containing 25C-NBOMe
Wikimedia Commons has media related to 2C-C-NBOMe.

25C-NBOMe (NBOMe-2C-C, 2C-C-NBOMe, Cimbi-82) is a

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

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 mucus membranes, but generally remain inactive when taken orally.

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

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

NBOMe compounds are often associated with life-threatening toxicity and death.

diaphoresis, hypertonia, rhabdomyolysis, and death.[15][19][13] Researchers report that NBOMe intoxication frequently display signs of serotonin syndrome.[20] The likelihood of seizure is higher in NBOMes compared to other psychedelics.[14]

NBOMe and NBOHs are regularly sold as LSD in blotter papers,[13][21] which have a bitter taste and different safety profiles.[15][12] Despite high potency, recreational doses of LSD have only produced low incidents of acute toxicity.[12] Fatalities involved in NBOMe intoxication suggest that a significant number of individuals ingested the substance which they believed was LSD,[17] and researchers report that "users familiar with LSD may have a false sense of security when ingesting NBOMe inadvertently".[15] While most fatalities are due to the physical effects of the drug, there have also been reports of death due to self-harm and suicide under the influence of the substance.[22][23][15]

Given limited documentation of NBOMe consumption, the long-term effects of the substance remain unknown.
numbness of the tongue and mouth followed by a metallic chemical taste was observed, and researchers describe this physical side effect as one of the main discriminants between NBOMe compounds and LSD.[26][27][28]

Neurotoxic and cardiotoxic actions

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

Many of the NBOMe compounds have high potency agonist activity at additional 5-HT receptors and prolonged activation of 5-HT2B can cause cardiac valvulopathy in high doses and chronic use.[13][18] 5-HT2B receptors have been strongly implicated in causing drug-induced valvular heart disease.[29][30][31] The high affinity of NBOMe compounds for adrenergic α1 receptor has been reported to contribute to the stimulant-type cardiovascular effects.[18]

In vitro studies, 25C-NBOMe has been shown to exhibit cytotoxicity on neuronal cell lines SH-SY5Y, PC12, and SN471, and the compound was more potent than methamphetamine at reducing the visibility of the respective cells; the neurotoxicity of the compound involves activation of MAPK/ERK cascade and inhibition of Akt/PKB signaling pathway.[14] 25C-NBOMe, including the other derivative 25D-NBOMe, reduced the visibility of cardiomyocytes H9c2 cells, and both substances downregulated expression level of p21 (CDC24/RAC)-activated kinase 1 (PAK1), an enzyme with documented cardiac protective effects.[14]

Preliminary studies on 25C-NBOMe have shown that the substance is toxic to development, heart health, and brain health in zebrafish, rats, and Artemia salina, a common organism for studying potential drug effects on humans, but more research is needed on the topic, the dosages, and if the toxicology results apply to humans. Researchers of the study also recommended further investigation of the drug's potential in damaging pregnant women and their fetus due to the substance's damaging effects to development.[32][33]

Emergency treatment

This section is an excerpt from 25-NB § Emergency treatment.[edit]
At present, there are no specific antidotes for NBOMes, and all acute intoxication is managed by symptomatic treatments, such as administration of benzodiazepines, antipsychotic drugs, and antiarrhythmic agents, such as beta blockers; some emergency interventions are intended to specifically treat rhabdomyolysis, which may lead to critical complications such as metabolic acidosis and acute kidney injury.[14]

Drug prohibition laws

Canada

As of October 31, 2016; 25C-NBOMe is a controlled substance (Schedule III) in Canada.[34]

Israel

The NBOMe series of psychoactives became controlled in Israel in May, 2013.[35][36]

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.[37]

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.[35][38]

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.[39]

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.[40]

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.[41] In November 2015, the temporary scheduling was extended for another year.[42]

China

As of October 2015 25C-NBOMe is a controlled substance in China.[43]

Czech Republic

25C-NBOMe is banned in the Czech Republic.[44]

Analogues and derivatives

Analogues and derivatives of 2C-C:

25C-NB*:

N-(2C)-fentanyl
:

Notes

  1. ^ The potency of N-benzylphenethylamines via buccal, sublingual, or nasal absorption is 50-100 greater (by weight) than oral route compared to the parent 2C-x compounds.[24] Researchers hypothesize the low oral metabolic stability of N-benzylphenethylamines is likely causing the low bioavailability on the oral route, although the metabolic profile of this compounds remains unpredictable; therefore researchers state that the fatalities linked to these substances may partly be explained by differences in the metabolism between individuals.[24]

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. ^ "Substance Details 25C-NBOMe". Retrieved 2024-01-23.
  3. ^
    S2CID 12467684
    .
  4. PMID 24397362
    .
  5. doi:10.13140/RG.2.2.33671.14245
    .
  6. PMID 22989597
    .
  7. S2CID 214704393
    .
  8. S2CID 209388281
    .
  9. ^ 2C-C-NBOMe Dose - erowid
  10. PMID 24770890
    .
  11. PMID 32174803
    .
  12. ^
    S2CID 247764056
    .
  13. ^
    PMID 30261175
    .
  14. ^
    PMID 32174803
    .
  15. ^
    S2CID 247888583
    .
  16. PMID 35530025
    .
  17. ^
    PMID 31915427
    .
  18. ^
    S2CID 10382311
    .
  19. ^
    S2CID 25752763
    .
  20. ISSN 1923-4163
    .
  21. PMID 26378135
    .
  22. PMID 28893436
    .
  23. S2CID 4734566
    .
  24. ^
    S2CID 254857910
    .
  25. PMID 28097528
    .
  26. PMID 27406128
    .
  27. PMID 25105138
    .
  28. S2CID 240583877
    .
  29. PMID 11104741
    .
  30. PMID 10617681
    .
  31. PMID 17202450
    .
  32. S2CID 255763701
    .
  33. PMID 33598409
    .
  34. ^ "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.
  35. ^ a b "NBOMe Series Legal Status". Erowid. Retrieved 5 September 2015.
  36. ^ "Amendment to Dangerous Drugs Ordinance". Israeli Ministry of Health. 7 June 2013. Retrieved 11 September 2015.
  37. ^ 'Legal high' DIME not so legal. Science Media Centre, March 13th 2012
  38. ^ "Постановление Правительства Российской Федерации от 6 октября 2011 г. N 822 г. Москва" (in Russian). 19 October 2011. Retrieved 5 September 2015.
  39. ^ Åkerman CR (24 July 2013). "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" (PDF). Retrieved 5 September 2015.
  40. ^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
  41. ^ Harrigan TM (10 October 2013). "Proposed Rules" (PDF). Drug Enforcement Administration (DEA). Retrieved 5 September 2015.
  42. PMID 26567439
    .
  43. ^ "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.
  44. ^ "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. Archived from the original (PDF) on 2016-03-09. Retrieved 2016-02-06.
  45. ^ "Explore N-(2C-C)-Fentanyl | PiHKAL · info". isomerdesign.com.
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