25C-NBOMe

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.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

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.2C-C-NBOMe Dose - erowid

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 2,353–>10,000 5-HT1B 2,372–>10,000 5-HT1D 1,024–1,109 5-HT1E 5,776–>10,000 5-HT1F 5-HT2A 0.7–1.6 (Ki)1.46–150 ()82–167% () 5-HT2B 1.05 (Ki)100 ()16% () 5-HT2C 2.54–5.4 (Ki)3.24 ()103% () 5-HT3 >10,000 5-HT4 5-HT5A 4,796–>10,000 5-HT6 36.2–36.3 5-HT7 1,729–>10,000 α1A 810–>10,000 α1B >10,000 α1D >10,000 α2A 313–3,175 α2B 224–871 α2C 185–347 β1 β2 2,630β3 >10,000 D1 12,000 D2 1,600–7,508 D3 878–>10,000 D4 2,018–>10,000 D5 >10,000 H1 65.3–90 H2 1,230 H3–H4 M1–M3 >10,000 M4 5,410 M5 >10,000 I1 σ1 221–441 σ2 41–79.4 MOR 653 (Ki)10,000–>122,000 ()<5–82% () DOR >10,000 KOR 525 15,000 (Ki) (mouse)520 (Ki) (rat)6,700 () (mouse)1,600 () (rat)>10,000 () (human)48% () (mouse)29% () (rat) 923–>10,000 (Ki)7,300 () () 1,600–>10,000 (Ki)5,900 () () 14,000 (Ki)70,000 () () Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: Hansen, M. (2010). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain: PhD Thesis. Faculty of Pharmaceutical Sciences, University of Copenhagen. https://bitnest.netfirms.com/external/Theses/Hansen2011

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. It has also been found to producing long-lasting social avoidance via hippocampal–prefrontal desynchrony when given repeatedly to adolescent 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.'Legal high' DIME not so legal. Science Media Centre, March 13th 2012

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.

25C-NBOMe

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