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25C-NBOMe
Psychedelic drug
Psychedelic drug
25C-NBOMe, also known as NBOMe-2C-C, 2C-C-NBOMe, or Cimbi-82, is a psychedelic drug and derivative of the psychedelic phenethylamine 2C-C. It acts as a potent agonist of the 5-HT2A receptor, 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). 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. 25C-NBOMe was first described in the scientific literature by 2010.
Use and effects

25C-NBOMe is extremely potent and the effects of the drug increase greatly within a small window of dose 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.
One study has shown that 25C-NBOMe blotters have 'hotspots' of the drug and the dose is not evenly applied over the surface of the paper, which could lead to overdose. 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.
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.
Toxicity and harm potential
Neurotoxic and cardiotoxic actions
Emergency treatment
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| [5-HT1A](5-ht1a-receptor) | 2,353–5,000 |
| [5-HT1B](5-ht1b-receptor) | 2,372 |
| [5-HT1D](5-ht1d-receptor) | 1,024 |
| [5-HT1E](5-ht1e-receptor) | 5,776 |
| [5-HT1F](5-ht1f-receptor) | ND |
| [5-HT2A](5-ht2a-receptor) | 0.7–1.6 (Ki) |
| 1.46–150 () | |
| 82–167% () | |
| [5-HT2B](5-ht2b-receptor) | 1.1 (Ki) |
| 100 (EC50) | |
| 16% (Emax) | |
| [5-HT2C](5-ht2c-receptor) | 5.2–5.4 (Ki) |
| 3.24 (EC50) | |
| 103% (Emax) | |
| [5-HT3](5-ht3-receptor) | 10,000 |
| [5-HT4](5-ht4-receptor) | ND |
| [5-HT5A](5-ht5a-receptor) | 4,796 |
| [5-HT6](5-ht6-receptor) | 36.2 |
| [5-HT7](5-ht7-receptor) | 1,729 |
| α1A | 810–2,319 |
| α1B | 10,000 |
| α1D | 10,000 |
| α2A | 560–3,175 |
| α2B | 224 |
| α2C | 185 |
| β1–β3 | ND |
| D1 | 12,000 |
| D2 | 1,600–7,508 |
| D3 | 878–3,500 |
| D4 | 10,000 |
| D5 | 10,000 |
| H1 | 90 |
| H2–H4 | ND |
| M1–M3 | 10,000 |
| M4 | 5,410 |
| M5 | 10,000 |
| I1 | ND |
| σ1 | 441 |
| σ2 | 41 |
| MOR | ND (Ki) |
| 10,000–122,000 (EC50) | |
| max | maximal efficacy}}) |
| DOR | ND |
| KOR | ND |
| 15,000 (Ki) (mouse) | |
| 520 (Ki) (rat) | |
| 6,700 (EC50) (mouse) | |
| 1,600 (EC50) (rat) | |
| 10,000 (EC50) (human) | |
| 48% (Emax) (mouse) | |
| 29% (Emax) (rat) | |
| 1,500–10,000 (Ki) | |
| 7,300 () | |
| ND (EC50) | |
| 1,600–10,000 (Ki) | |
| 5,900 (IC50) | |
| ND (EC50) | |
| 14,000 (Ki) | |
| 70,000 (IC50) | |
| ND (EC50) | |
| **Notes:** The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. **Refs:** |
25C-NBOMe acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor.
25C-NBOMe has been found to produce neurotoxicity in rodents.
Chemistry
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.
Analogues
Analogues of 25C-NBOMe include 2C-C, DOC, 25I-NBOMe, 25B-NBOMe, 25C-NBOH, 25C-NB3OMe, 25C-NB4OMe, and 25C-NBF, among others.
History
25C-NBOMe was first described in the scientific literature by Anders Ettrup and colleagues by 2010.
Society and culture
Recreational use
25C-NBOMe has been found on blotter mimics sold as LSD.
Legal status
Canada
As of October 31, 2016; 25C-NBOMe is a controlled substance (Schedule III) in Canada.
China
As of October 2015, 25C-NBOMe is a controlled substance in China.
Czech Republic
25C-NBOMe is banned in the Czech Republic.
Israel
The NBOMe series of psychoactives became controlled in Israel in May, 2013.
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.
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.
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.
United Kingdom
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. In November 2015, the temporary scheduling was extended for another year. Subsequently, they became permanently controlled.
Notes
References
References
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- (2010-12-16). "Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain.". University of Copenhagen.
- Ettrup, A. (2010). Serotonin receptor studies in the pig brain: pharmacological intervention and positron emission tomography tracer development (Doctoral dissertation, Faculty of Health Sciences, University of Copenhagen). https://research.regionh.dk/en/publications/serotonin-receptor-studies-in-the-pig-brain-pharmacological-inter
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- (27 September 2015). "关于印发《非药用类麻醉药品和精神药品列管办法》的通知". China Food and Drug Administration.
- "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)". Ministerstvo zdravotnictví.
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- [http://www.sciencemediacentre.co.nz/2012/03/13/legal-high-dime-not-so-legal/ 'Legal high' DIME not so legal. Science Media Centre, March 13th 2012]
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- Drug Enforcement Administration. (November 2015). "Schedules of Controlled Substances: Extension of Temporary Placement of Three Synthetic Phenethylamines in Schedule I. Final order". Federal Register.
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