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25I-NBOMe (2C-I-NBOMe, Cimbi-5, Smiles and also shortened to "25I") is a synthetic hallucinogen that is used in biochemistry research for mapping the brain's usage of the type 2A serotonin receptor; it is also sometimes used for recreational purposes. A derivative of the substituted phenethylamine 2C-I family, it is the most well-known member of the 25-NB family. It was discovered in 2003 by chemist Ralf Heim at the Free University of Berlin, who published his findings in his PhD dissertation. The compound was subsequently investigated by a team at Purdue University led by David Nichols.

The carbon-11 labelled version of 25I-NBOMe, [11C]Cimbi-5, was synthesized and validated as a radiotracer for positron emission tomography (PET) in Copenhagen. Being the first 5-HT2A receptor full agonist PET radioligand, [11C]-CIMBI-5 shows promise as a more functional marker of these receptors, particularly in their high affinity states.

Street and media nicknames for this drug are: "N-Bomb", "Solaris", "Smiles", and "Wizard", although the drug is frequently fraudulently sold as LSD.

Due to its physical effects and risk of overdose, there have been multiple deaths attributed to the drug. Its long term toxicity is unknown due to lack of existing research.

Effects

25I-NBOMe effects usually last 6–10 hours if taken sublingually, or buccally (between gum and cheek).[16] When it is insufflated (snorted), effects usually last 4–6 hours.

25I-NBOMe has similar effects to LSD, though users report more negative effects while under the influence and more risk of harm following use as compared to the classical psychedelics.

Case reports of seven British males who presented to an emergency room following analytically confirmed 25I-NBOMe intoxication suggest the following potential adverse effects: "tachycardia (n = 7), hypertension (4), agitation (6), aggression, visual and auditory hallucinations (6), seizures (3), hyperpyrexia (3), clonus (2), elevated white blood cell count (2), elevated creatine kinase (7), metabolic acidosis (3), and acute kidney injury (1). 25I-NBOMe can be consumed in liquid, powder or paper form and can be snorted, injected, mixed with food, or smoked, but sublingual administration is most common.

Toxicity

Recreational use of 25I-NBOMe carries a significant risk of both pharmacological and behavioral toxicity.[12][15] 25I-NBOMe is a relatively new substance, and little is known about its pharmacological risks or its interaction with other substances, although multiple deaths have occurred while under the effects of 25I-NBOMe and other drugs. The LD50 has not yet been determined.[21] The long-term toxicity of 25I-NBOMe is unknown due to lack of research.  NBOMe chemicals, including 25I-NBOMe, frequently cause tachycardia (rapid heart rate), hypertension (high blood pressure), and vasoconstriction (which reduces blood flow). These physical symptoms can cause significant risks to health, especially when the user has underlying health issues or has taken a combination of drugs.25I-NBOMe presumably exhibits functional selectivity at the 5HT2A receptor similar to other phenethylamine hallucinogens, activating the Phospholipase A2 signal cascade,[23] which is responsible for the release of Thromboxane A2, triggering blood platelet aggregation. Excessive concentrations of TXA2 could lead to thrombosis, which when coupled with 25I-NBOMe's vasoconstrictive effect, is a major risk factor for cardiac ischemia, a dangerous condition the symptoms of which are present in several toxicological reports. One 16-year-old was studied in 2017 after reporting seizures attributed to 25I-NBOMe usage, which after 18 months culminated in progressive left-sided weakness, ataxia, facial droop, executive dysfunction. An MRI revealed the patient to have brain damage revealed by an MRI to be bilateral leukoencephalopathy concurrent with symptoms of serotonin syndrome. According to the researchers 'patients with 25I-NBOMe toxicity frequently display signs of serotonin syndrome

Recreational use

Although 25I-NBOMe was discovered in 2003, it did not emerge as a common recreational drug until 2010, when it was first sold by vendors specializing in the supply of designer drugs.[9] In a slang context, the name of the compound is often shortened to "25I" or is simply called "N-Bomb".[10] According to a 2014 survey, 25I-NBOMe was the most frequently used of the NBOMe series.[11] By 2013, case reports of 25I-NBOMe intoxication, with and without analytic confirmation of the drug in the body, were becoming increasingly common in the medical literature.

25I-NBOMe is widely rumored to be orally inactive; however, apparent overdoses have occurred via oral administration. Common routes of administration include sublingual, buccal, and intranasal.For sublingual and buccal administration, 25I-NBOMe is often applied to sheets of blotter paper of which small portions (tabs) are held in the mouth to allow absorption through the oral mucosa. There are reports of intravenous injection of 25I-NBOMe solution and smoking the drug in powdered form.

Due to its potency and much lower cost than so-called classical or traditional psychedelics, 25I-NBOMe blotters are frequently misrepresented as, or mistaken for, LSD blotters.[17] Even small quantities of 25I-NBOMe can produce a large number of blotters. Vendors would import 25I-NBOMe in bulk (e.g. 1 kg containers) and resell individual doses for a considerable profit.

Dosage

25I-NBOMe is potent, being active in sub-milligram doses. A common dose of the hydrochloride salt is 600–1,200 μg. The UK Advisory Council on the Misuse of Drugs states that a common dose is between 50 and 100 μg,[14] although other sources indicate that these figures are incorrect; Erowid tentatively suggests that the threshold dosage for humans is 50–250 μg, with a light dose between 200–600 μg, a common dose at 500–800 μg, and a strong dose at 700–1500 μg.

At this level of potency, it is not possible to accurately measure a single dose of 25I-NBOMe powder without an analytical balance, and attempting to do so may put the user at significant risk of overdose.There is a high risk of overdose due to the small margin between a high-dose and an over-dose, which is not a risk with the similar drug LSD. One study has shown that 25I-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

Chemistry

Like other 2C-X-NBOMe molecules, 25I-NBOMe is a derivative of the 2C family of phenethylamines described by chemist Alexander Shulgin in his book PiHKAL.[14][12] Specifically, 25I-NBOMe is an N-benzyl derivative of the phenethylamine molecule 2C-I, formed by adding a 2-methoxybenzyl (BnOMe) onto the nitrogen (N) of the phenethylamine backbone. This substitution significantly increases the potency of the molecule

Pharmacology

25I-NBOMe acts as a highly potent full agonist for the human 5-HT2A receptor,[35][37] with a dissociation constant (Kd) of 0.044 nM, making it some sixteen times the potency of 2C-I itself at this receptor. A radiolabelled form of 25I-NBOMe can be used for mapping the distribution of 5-HT2A receptors in the brain