25I-NBOMe, also known as 2C-I-NBOMe, Cimbi-5, and shortened to "25I", is a

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...

of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

, 2C, and

NBOMe The 25-NB (25''x''-NB''x'') series, or NBOMe series, also known as the ''N''-benzylphenethylamines, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C (psychedelics), 2C family. The most c ...

(25-NB) families. Since 2010, it has circulated in the

recreational drug Recreational drug use is the use of one or more psychoactive drugs to induce an altered state of consciousness, either for pleasure or for some other casual purpose or pastime. When a psychoactive drug enters the user's body, it induces an Sub ...

scene, often misrepresented as

LSD Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a semisynthetic, hallucinogenic compound derived from ergot, known for its powerful psychological effects and serotonergic activity. I ...

. It is the most well-known member of the 25-NB family and the earliest member to be encountered as a novel recreational drug. The

carbon-11 Carbon (6C) has 14 known isotopes, from to as well as , of which only and are stable nuclide, stable. The longest-lived radionuclide, radioisotope is , with a half-life of years. This is also the only carbon radioisotope found in nature, as ...

labelled version of 25I-NBOMe, sup>11Cimbi-5, was synthesized and validated as a

radiotracer A radioactive tracer, radiotracer, or radioactive label is a synthetic derivative of a natural compound in which one or more atoms have been replaced by a radionuclide (a radioactive atom). By virtue of its radioactive decay, it can be used to ...

for

positron emission tomography Positron emission tomography (PET) is a functional imaging technique that uses radioactive substances known as radiotracers to visualize and measure changes in metabolic processes, and in other physiological activities including blood flow, r ...

(PET) in Copenhagen. Being the first 5-HT_2A receptor full agonist PET radioligand, sup>11CIMBI-5 shows promise as a more functional marker of these receptors, particularly in their high affinity states. Street and media nicknames for this drug include "N-Bomb", "Solaris", "Smiles", and "Wizard", although the drug is frequently fraudulently sold as LSD.Mackin, Teresa (October 9, 2012)
Dangerous synthetic drug making its way across the country.

WISH-TV WISH-TV (channel 8) is a television station in Indianapolis, Indiana, United States, affiliated with The CW. It is locally owned by Circle City Broadcasting alongside Marion-licensed MyNetworkTV affiliate WNDY-TV (channel 23) and low-power, ...

Due to its physical effects and risk of

overdose A drug overdose (overdose or OD) is the ingestion or application of a drug or other substance in quantities much greater than are recommended. Retrieved on September 20, 2014.

, there have been multiple deaths attributed to the drug. Its long-term

toxicity Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacteria, bacterium, or plant, as well as the effect o ...

is unknown due to lack of existing research. 25I-NBOMe was first described in 2000. It was first encountered as a novel recreational drug in 2010, and by 2012, NBOMes like 25I-NBOMe had surpassed other major psychedelics like

and

psilocybin-containing mushroom Psilocybin mushrooms, or psilocybin-containing mushrooms, commonly known as magic mushrooms or as shrooms, are a type of hallucinogenic mushroom and a polyphyletic informal group of fungi that contain the prodrug psilocybin, which turns into t ...

s in popularity, at least for a time. 25I-NBOMe became a

controlled substance A controlled substance is generally a drug or chemical whose manufacture, possession and use is regulated by a government, such as illicitly used drugs or prescription medications that are designated by law. Some treaties, notably the Sing ...

in the

United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

in 2013.

Use

Recreational

Although 25I-NBOMe was first described by 2000, it did not emerge as a common recreational drug until 2010, when it was first sold by vendors specializing in the supply of

designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. ...

s. In a slang context, the name of the compound is often shortened to "25I" or is simply called "N-Bomb". According to a 2014 survey, 25I-NBOMe was the most frequently used of the NBOMe series. 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 Sublingual (List of abbreviations used in medical prescriptions, abbreviated SL), from the Latin for "under the tongue", refers to the pharmacological route of administration by which substances diffuse into the blood through Tissue (biology), t ...

, buccal, and

intranasal Nasal administration, popularly known as snorting, is a route of administration in which drugs are insufflation (medicine), insufflated through the nose. It can be a form of either topical administration or systemic administration, as the drugs t ...

. 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

blotters. 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 In the metric system, a microgram or microgramme is a Physical unit, unit of mass equal to one millionth () of a gram. The unit symbol is μg according to the International System of Units (SI); the recommended symbol in the United States and Uni ...

. The UK Advisory Council on the Misuse of Drugs states that a common dose is between 50 and 100 μg, although other sources indicate that these figures are incorrect;

Erowid Erowid, also called Erowid Center, is a non-profit educational organization that provides information about psychoactive plants and chemicals. Erowid documents legal and illegal substances, including their intended and adverse effects. Inform ...

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 An analytical balance (or chemical ''balance'') is a class of balance designed to measure small mass in the sub-milligram range. The measuring pan of an analytical balance (0.1 mg resolution or better) is inside a transparent enclosure with do ...

, 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

. 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.

Effects

25I-NBOMe effects usually last 6–10 hours if taken sublingually, or buccally (between gum and cheek). 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 Tachycardia, also called tachyarrhythmia, is a heart rate that exceeds the normal resting rate. In general, a resting heart rate over 100 beats per minute is accepted as tachycardia in adults. Heart rates above the resting rate may be normal ...

(n = 7),

hypertension Hypertension, also known as high blood pressure, is a Chronic condition, long-term Disease, medical condition in which the blood pressure in the artery, arteries is persistently elevated. High blood pressure usually does not cause symptoms i ...

(4), agitation (6),

aggression Aggression is behavior aimed at opposing or attacking something or someone. Though often done with the intent to cause harm, some might channel it into creative and practical outlets. It may occur either reactively or without provocation. In h ...

visual The visual system is the physiological basis of visual perception (the ability to detect and process light). The system detects, transduces and interprets information concerning light within the visible range to construct an image and buil ...

and auditory

hallucinations A hallucination is a perception in the absence of an external stimulus that has the compelling sense of reality. They are distinguishable from several related phenomena, such as dreaming ( REM sleep), which does not involve wakefulness; pse ...

(6),

seizures A seizure is a sudden, brief disruption of brain activity caused by abnormal, excessive, or synchronous neuronal firing. Depending on the regions of the brain involved, seizures can lead to changes in movement, sensation, behavior, awareness, o ...

(3),

hyperpyrexia Fever or pyrexia in humans is a symptom of an anti-infection defense mechanism that appears with body temperature exceeding the normal range caused by an increase in the body's temperature set point in the hypothalamus. There is no single agre ...

(3),

clonus Clonus is a set of involuntary and rhythmic muscular contractions and relaxations. Clonus is a sign of certain neurological conditions, particularly associated with upper motor neuron lesions involving descending motor pathways, and in many cas ...

(2), elevated

white blood cell White blood cells (scientific name leukocytes), also called immune cells or immunocytes, are cells of the immune system that are involved in protecting the body against both infectious disease and foreign entities. White blood cells are genera ...

count (2), elevated

creatine kinase Creatine kinase (CK), also known as creatine phosphokinase (CPK) or phosphocreatine kinase, is an enzyme () expressed by various tissues and cell types. CK catalyses the conversion of creatine and uses adenosine triphosphate (ATP) to create phos ...

(7),

metabolic acidosis Metabolic acidosis is a serious electrolyte disorder characterized by an imbalance in the body's acid-base balance. Metabolic acidosis has three main root causes: increased acid production, loss of bicarbonate, and a reduced ability of the kidn ...

(3), and

acute kidney injury Acute kidney injury (AKI), previously called acute renal failure (ARF), is a sudden decrease in renal function, kidney function that develops within seven days, as shown by an increase in serum creatinine or a decrease in urine output, or both. ...

(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.

Interactions

2C drugs like

2C-I 2C-I, also known as 2,5-dimethoxy-4-iodophenethylamine, is a phenethylamine of the 2C family with psychedelic effects. It was first synthesized by Alexander Shulgin, and is described in Shulgin's book ''PiHKAL'' (1991). The substance is con ...

are

metabolized Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...

by the

monoamine oxidase Monoamine oxidases (MAO) () are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine group. They are found bound to the outer membrane of mitochondria in most cell types of the body. The fi ...

(MAO)

enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...

s, including both

MAO-A Monoamine oxidase A, also known as MAO-A, is an enzyme ( E.C. 1.4.3.4) that in humans is encoded by the ''MAOA'' gene. This gene is one of two neighboring gene family members that encode mitochondrial enzymes which catalyze the oxidative deamin ...

and

MAO-B Monoamine oxidase B (MAO-B) is an enzyme that in humans is encoded by the ''MAOB'' gene. The protein encoded by this gene belongs to the flavin monoamine oxidase family. It is an enzyme located in the outer mitochondrial membrane. It catalyze ...

. As a result, 2C drugs may be potentiated by

monoamine oxidase inhibitor Monoamine oxidase inhibitors (MAOIs) are a drug class, class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressa ...

s (MAOIs), such as

phenelzine Phenelzine, sold under the brand name Nardil among others, is a non-selective and irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine family which is primarily used as an antidepressant and anxiolytic to treat depression and a ...

tranylcypromine Tranylcypromine, sold under the brand name Parnate among others, is a monoamine oxidase inhibitor (MAOI). More specifically, tranylcypromine acts as nonselective and irreversible inhibitor of the enzyme monoamine oxidase (MAO). It is used a ...

moclobemide Moclobemide, sold under the brand names Amira, Aurorix, Clobemix, Depnil and Manerix among others, is a reversible inhibitor of monoamine oxidase A (RIMA) drug primarily used to treat Clinical depression, depression and social anxiety. It is not ...

, and

selegiline Selegiline, also known as L-deprenyl and sold under the brand names Eldepryl, Zelapar, and Emsam among others, is a medication which is used in the treatment of Parkinson's disease and major depressive disorder. It has also been studied and us ...

. This has the potential to lead to

overdose A drug overdose (overdose or OD) is the ingestion or application of a drug or other substance in quantities much greater than are recommended. Retrieved on September 20, 2014.

and serious

. In contrast to 2C drugs, 25I-NBOMe has been found not to be metabolized by MAO-A or MAO-B and instead only by

cytochrome P450 Cytochromes P450 (P450s or CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that mostly, but not exclusively, function as monooxygenases. However, they are not omnipresent; for examp ...

enzymes. Other 25-NB drugs besides 25I-NBOMe were not assessed.

Toxicity and harm potential

Neurotoxic and cardiotoxic actions

Emergency treatment

Attributed deaths

Reports of deaths and significant injuries have been attributed to the use of 25I-NBOMe, prompting some governments to control its possession, production, and sale. The website

states that 25I-NBOMe is extremely potent and should not be snorted, and that the drug "appears to have led to several deaths in the past year." Several non-fatal overdoses requiring prolonged hospitalization have also been reported. As of August 2015, 25I-NBOMe has reportedly led to at least 19 overdose deaths in the United States. In June 2012, two teens in

Grand Forks, North Dakota Grand Forks is a city in and the county seat of Grand Forks County, North Dakota, United States. The city's population was 59,166 as of the 2020 United States census, 2020 census, making it the List of cities in North Dakota, third-most populous ...

and

East Grand Forks, Minnesota East Grand Forks (also known as EGF) is a city in Polk County, Minnesota, Polk County, Minnesota, United States. The population was 9,176 at the 2020 United States census, 2020 census, making it Polk County's largest community. It is in the Red ...

fatally overdosed on a substance that was allegedly 25I-NBOMe, resulting in lengthy sentences for two of the parties involved and a Federal indictment against the Texas-based online vendor. A 21-year-old man from

Little Rock, Arkansas Little Rock is the List of capitals in the United States, capital and List of municipalities in Arkansas, most populous city of the U.S. state of Arkansas. The city's population was 202,591 as of the 2020 census. The six-county Central Arkan ...

died in October 2012 after taking a liquid drop of the drug nasally at a music festival. He was reported to have consumed caffeinated alcoholic beverages for "several hours" beforehand. It is unclear what other drugs he may have consumed, as autopsies generally do not test for the presence of research chemicals. In January 2013, an 18-year-old in Scottsdale, Arizona, died after consuming 25I-NBOMe sold as LSD; a toxicology screening found no other drugs in the person's system. The drug is the suspected cause of death in another Scottsdale, Arizona, incident in April 2013. It is also cited in the death of a 21-year-old woman in August 2013 and the death of a 17-year-old in Minnesota in January 2014, as well as the death of a 15-year old in Washington in September 2014. In October 2015, a 20-year-old UCSB student from Isla Vista, California died of "acute hallucinogenic polysubstance intoxication" with an additional significant cause of death being "sharp force trauma of the upper extremity", according to a statement from Santa Barbara County Sheriff's office; the autopsy determined Sanchez was under the influence of two hallucinogenic drugs at the time of his death: ketamine and 25I-NBOMe. The noted sharp force trauma refers to a deep cut on Sanchez's right forearm, which was caused when he punched and broke a large residential window while suffering hallucinations. 25I-NBOMe has been implicated in multiple deaths in Australia. In March 2012, a man in Australia died from injuries sustained by running into trees and power poles while intoxicated by 25I-NBOMe. A Sydney teenager jumped off a balcony to his death on June 5, 2013, while on 25I-NBOMe. In July 2015, 25I-NBOMe was involved in the death of 18-year-old Liam Miller in York, England. Miller was stabbed 32 times by his close friend, Samuel Donley, during a psychotic episode after both had ingested the drug. Donley also attacked a passer-by and inflicted self-injuries before being detained. He pleaded guilty to manslaughter on the grounds of diminished responsibility and was sentenced to six years and eight months in prison. The court described the incident as a "drug-crazed frenzy" and highlighted the extreme psychological effects associated with 25I-NBOMe. 25I-NBOMe has been linked to a major case on January 20, 2016, in

Cork "Cork" or "CORK" may refer to: Materials * Cork (material), an impermeable buoyant plant product ** Stopper (plug), or "cork", a cylindrical or conical object used to seal a container *** Wine cork an item to seal or reseal wine Places Ireland * ...

Ireland Ireland (, ; ; Ulster Scots dialect, Ulster-Scots: ) is an island in the North Atlantic Ocean, in Northwestern Europe. Geopolitically, the island is divided between the Republic of Ireland (officially Names of the Irish state, named Irelan ...

, which left six teenagers hospitalized, one of whom later died. At least one of the teenagers suffered a

cardiac arrest Cardiac arrest (also known as sudden cardiac arrest CA is when the heart suddenly and unexpectedly stops beating. When the heart stops beating, blood cannot properly Circulatory system, circulate around the body and the blood flow to the ...

, according to reports, along with extreme internal bleeding. At least one suicide, and two attempted suicides leading to hospitalisation, have occurred while under the effects of 25I-NBOMe.

Pharmacology

Pharmacodynamics

25I-NBOMe acts as a highly potent full

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

for the

human Humans (''Homo sapiens'') or modern humans are the most common and widespread species of primate, and the last surviving species of the genus ''Homo''. They are Hominidae, great apes characterized by their Prehistory of nakedness and clothing ...

5-HT_2A

receptor Receptor may refer to: * Sensory receptor, in physiology, any neurite structure that, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and respond ...

, with a

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

(''K''_i) of 0.044 nM, making it some 16-fold higher affinity than

at this receptor. 25I-NBOMe induces a

head-twitch response The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lys ...

in mice which is blocked completely by a selective 5-HT_2A antagonist, suggesting its psychedelic effects are mediated by 5-HT_2A. This study suggested that 25I-NBOMe is approximately 14-fold more potent than 2C-I ''in-vivo''. While ''in-vitro'' studies showed that ''N''-benzyl derivatives of 2C-I were significantly increased in potency compared to 2C-I, the ''N''-benzyl derivatives of the related compound DOI were inactive. 25B-NBOMe is a low-

potency Potency may refer to: * Potency (pharmacology), a measure of the activity of a drug in a biological system * Virility * Cell potency, a measure of the differentiation potential of stem cells * In homeopathic dilutions, potency is a measure of ho ...

weak

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...

of the rat and mouse

trace amine-associated receptor 1 Trace amine-associated receptor 1 (TAAR1) is a trace amine-associated receptor (TAAR) protein that in humans is encoded by the ''TAAR1'' gene. TAAR1 is a primarily intracellular amine-activated and G protein-coupled receptor (GPCR) that is p ...

(TAAR1) but is inactive at the human TAAR1. The affinities and potencies of 25I-NBOMe at the serotonin 5-HT₂ receptors have varied in different studies. Its affinities (K_i) have ranged from 0.044 to 0.6nM for the serotonin 5-HT_2A receptor, 1.91 to 130nM for the serotonin 5-HT_2B receptor, and 1.03 to 4.6nM for the serotonin 5-HT_2C receptor. Conversely, its potencies () have ranged from 0.76 to 240nM at the serotonin 5-HT_2A receptor, 111 to 130nM at the serotonin 5-HT_2B receptor, and 2.38 to 88.9nM at the serotonin 5-HT_2C receptor. 25I-NBOMe also has weaker interactions with multiple other receptors. ''K''_d values for interaction with the following targets were greater than 500nM: 5-HT_1A, D₃, H₂, 5-HT_1D, α_1A adrenergic, δ opioid, serotonin uptake transporter, 5-HT_5A, 5-HT_1B, D₂, 5-HT₇, D₁, 5-HT₃, 5-HT_1E, D₅, muscarinic M₁-M₅, H₃, and the dopamine uptake transporter. 25I-NBOMe is inactive as a

monoamine reuptake inhibitor A monoamine reuptake inhibitor (MRI) is a drug that acts as a reuptake inhibitor of one or more of the three major monoamine neurotransmitters serotonin, norepinephrine, and dopamine by blocking the action of one or more of the respective monoamin ...

and releasing agent. However, 25I-NBOMe has been found to increase dopamine release from mouse striatal

synaptosome A synaptosome is an isolated synaptic terminal from a neuron. Synaptosomes are obtained by mild homogenization of nervous tissue under isotonic conditions and subsequent fractionation using differential and density gradient centrifugation. Liquid ...

s similarly to

methamphetamine Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug use, recreational or Performance-enhancing substance, performance-enhancing drug and less commonly as a secon ...

in vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...

''. Likewise, 25I-NBOMe has been found to increase

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...

levels in the

nucleus accumbens The nucleus accumbens (NAc or NAcc; also known as the accumbens nucleus, or formerly as the ''nucleus accumbens septi'', Latin for ' nucleus adjacent to the septum') is a region in the basal forebrain rostral to the preoptic area of the hypo ...

in rodents ''

in vivo Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, an ...

''. A

radiolabelled A radioactive tracer, radiotracer, or radioactive label is a synthetic derivative of a natural compound in which one or more atoms have been replaced by a radionuclide (a radioactive atom). By virtue of its radioactive decay, it can be used to exp ...

form of 25I-NBOMe can be used for mapping the distribution of 5-HT_2A receptors in the brain.

Pharmacokinetics

25I-NBOMe is

by the

CYP3A4 Cytochrome P450 3A4 (abbreviated CYP3A4) () is an important enzyme in the body, mainly found in the liver and in the intestine, which in humans is encoded by ''CYP3A4'' gene. It organic redox reaction, oxidizes small foreign organic molecules ( ...

and

CYP2D6 Cytochrome P450 2D6 (CYP2D6) is an enzyme that in humans is encoded by the ''CYP2D6'' gene. ''CYP2D6'' is primarily expressed in the liver. It is also highly expressed in areas of the central nervous system, including the substantia nigra. CYP2 ...

. It does not appear to be

by the

(MAO)

Chemistry

Like other 2C-''X''-NBOMe molecules, 25I-NBOMe is a derivative of the 2C family of phenethylamines described by chemist

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

in his book

PiHKAL ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...

. Specifically, 25I-NBOMe is an ''N''-benzyl derivative of the phenethylamine molecule

, formed by adding a 2-methoxybenzyl (BnOMe) onto the nitrogen (N) of the phenethylamine backbone. This substitution significantly increases the potency of the molecule.

Analogues

Another analogue of 25I-NBOMe is DOI-NBOMe.

Synthesis

25I-NBOMe is usually synthesised from 2C-I and

2-methoxybenzaldehyde 2-Methoxybenzaldehyde is an organic compound with the formula CH3OC6H4CHO. It is also commonly referred to as ''o''-anisaldehyde. As a methylated version of salicylaldehyde, the molecule consists of a benzene ring with adjacent formyl and a meth ...

, via reductive

alkylation Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

. It can be done stepwise by first making the

imine In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bon ...

and then reducing the formed imine with

sodium borohydride Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula (sometimes written as ). It is a white crystalline solid, usually encountered as an aqueous basic solution. Sodi ...

, or by direct reaction with

sodium triacetoxyborohydride Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula . Like other borohydrides, it is used as a reducing agent in organic synthesis. This colourless salt is pr ...

History

25I-NBOMe was first described in the

scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...

, in the form of

conference abstract An abstract is a brief summary of a research article, thesis, review, conference proceeding, or any in-depth analysis of a particular subject and is often used to help the reader quickly ascertain the paper's purpose. When used, an abstract always ...

s, by Ralf Heim and colleagues at the

Free University of Berlin The Free University of Berlin (, often abbreviated as FU Berlin or simply FU) is a public university, public research university in Berlin, Germany. It was founded in West Berlin in 1948 with American support during the early Cold War period a ...

by 2000. Then, in 2003, Heim described 25I-NBOMe in his dissertation. 25I-NBOMe was further investigated by a team at

Purdue University Purdue University is a Public university#United States, public Land-grant university, land-grant research university in West Lafayette, Indiana, United States, and the flagship campus of the Purdue University system. The university was founded ...

led by David Nichols in 2006 through 2008. 25I-NBOMe was encountered as a novel

by 2010, and by 2012, NBOMe drugs like 25I-NBOMe had eclipsed other psychedelics like

and

s in popularity, at least for a time. 25I-NBOMe became a Schedule I

in the

in 2013.

Society and culture

Legal status

Australia

25I-NBOMe was explicitly scheduled in Queensland drug law in April 2012, and in New South Wales in October 2013, as were some related compounds such as 25B-NBOMe. The Australian federal government has no specific legislation concerning any of the N-benzyl phenethylamines.

Brazil

All drugs in the NBOMe family, including 25I-NBOMe, are illegal.

Canada

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

China

As of October 2015 25I-NBOMe is a controlled substance in China.

European Union

In September 2014 the

European Union The European Union (EU) is a supranational union, supranational political union, political and economic union of Member state of the European Union, member states that are Geography of the European Union, located primarily in Europe. The u ...

implemented a ban of 25I-NBOMe in all its member states.

Finland

25I-NBOMe is scheduled in government decree on narcotic substances, preparations and plants as of 2022 and is hence illegal to possess or use.

Israel

Israel banned 25I-NBOMe in 2013.

Romania

In 2011, Romania banned all psychoactive substances.

Russia

Russia was the first country to pass specific regulations on the NBOMe series. All drugs in the NBOMe series, including 25I-NBOMe, became illegal in Russia in October 2011.

Serbia

25I-NBOMe was put on the list of prohibited substances in March 2015.

Sweden

The Riksdag added 25I-NBOMe to Narcotic Drugs Punishments Act under ''Swedish schedule I'' (''"substances, plant materials and fungi which normally do not have medical use"'') as of August 1, 2013, published by Medical Products Agency (MPA) in regulation ''LVFS 2013:15'' listed as 25I-NBOMe, and 2-(4-jodo-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.

Taiwan

Following the European rule from 2014, 25I-NBOMe was put in class 4 of prohibited substances.

United Arab Emirates

The UAE has a zero-tolerance policy for recreational use of drugs. Federal Law No. 14 of 1995 criminalises production, import, export, transport, buying, selling, possessing, storing of narcotic and psychotropic substances (Including 25i-NBOMe) unless done so as part of supervised and regulated medical or scientific activities in accordance with the applicable laws. The UAE police has dedicated departments to deal with drugs' issues.

United Kingdom

United States

On Nov 15, 2013, the DEA added 25I-NBOMe (and 25C-, and 25B-NBOMe) to Schedule I using their emergency scheduling powers, making those NBOMe compounds "temporarily" in Schedule I for 2 years. In November 2015, the temporary scheduling was extended for an additional year while permanent scheduling was arranged. 25I-NBOMe, 25B-NBOMe and 25C-NBOMe are currently Schedule 1 Substances according to 21 CFR 1308.11(d).

Notes

References

External links

25I-NBOMe - Isomer Design

25I-NBOMe - PsychonautWiki

25I-NBOMe - Erowid

The Big & Dandy 25I-NBOMe Thread - Bluelight

25I-NBOMe - TripSit.me

What Are N-Bombs? (25-I-NBOMe) — Avoid This Psychedelic - Tripsitter

Unmasking Fake Acid: The Dangers of 25I-NBOMe Disguised as LSD - Psychedelic Spotlight
{{Phenethylamines 25-NB (psychedelics) 5-HT2A agonists 5-HT2B agonists 5-HT2C agonists Designer drugs Iodobenzene derivatives 2-Methoxyphenyl compounds Psychedelic phenethylamines TAAR1 agonists