25E-NBOMe

25E-NBOMe, also known as 2C-E-NBOMe or NBOMe-2C-E, is a derivative of the phenethylamine 2C-E. It acts in a similar manner to related compounds such as 25I-NBOMe, which are potent agonists at the 5-HT2A receptor. 25E-NBOMe has been sold as a drug and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe.

Use and effects The dose range of 25E-NBOMe has been given as 0.1 to 1.0mg sublingually, with a typical dose estimate of 0.3mg.

Toxicity and harm potential

Neurotoxic and cardiotoxic actions

Emergency treatment

Interactions

Pharmacology Pharmacodynamics + Target Affinity (Ki, nM) 5-HT1A 1,680–3,500 (Ki)13,700 ()38% () 5-HT1B 3,593 5-HT1D 5-HT1E 5-HT1F 5-HT2A 0.127–0.6 (Ki)0.40–160 ()28–157% () 5-HT2B 1.11–2.14 (Ki)23.5–60 ()26–49% () 5-HT2C 0.311–7.2 (Ki)0.95–9.77 ()92–101% () 5-HT3 5-HT4 5-HT5A 5-HT6 148.3 5-HT7 α1A 530 α1B, α1D α2A 260 α2B, α2C β1–β3 D1 4,900 D2 1,500 D3 3,200 D4, D5 H1 1,400 H2–H4 M1–M5 I1 σ1, σ2 MOR (Ki)>12,400 ()20–103% () DOR KOR 1,100 (Ki) (mouse)260 (Ki) (rat)1,800 () (mouse)650 () (rat)>10,000 () (human)46% () (mouse)37% () (rat) 1,590–1,700 (Ki)1,440–8,300 () () 3,000–5,400 (Ki)2,310–11,000 () () 8,100–19,600 (Ki)34,000–100,000 () () 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

25E-NBOMe acts as an agonist of the serotonin 5-HT2 receptors. In accordance with its psychedelic effects in humans, it produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.

25E-NBOMe has shown reinforcing effects in rodents. This included conditioned place preference (CPP) and self-administration. The reinforcing effects of 25E-NBOMe were mediated by increased dopaminergic signaling in the nucleus accumbens. Blockade of the dopamine D1 receptor could attenuate the CPP induced by 25E-NBOMe.

History 25E-NBOMe was first described in the scientific literature by 2012.Casale, J. F., & Hays, P. A. (2012). Characterization of eleven 2, 5-dimethoxy-N-(2-methoxybenzyl) phenethylamine (NBOMe) derivatives and differentiation from their 3-and 4-methoxybenzyl analogues—part I. Microgram Journal, 9(2), 84–109. https://www.dea.gov/sites/default/files/pr/microgram-journals/2012/mj9_84-109.pdf

Society and culture Legal status Canada 25E-NBOMe is a controlled substance in Canada under phenethylamine blanket-ban language.

Sweden Sweden's public health agency classified 25E-NBOMe as a narcotic substance, on January 18, 2019.

United Kingdom

United States 25E-NBOMe is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

25E-NBOMe

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