25I-NBOMe

25I-NBOMe (2C-I-NBOMe, Cimbi-5, Smiles

and also shortened to "25I") is a novel synthetic 25I-NBOMe
psychoactive substance with strong hallucinogenic
properties, synthesized in 2003 for research
purposes. Since 2010, it has circulated in the
recreational drug scene, often misrepresented as
LSD. The recreational usage of 25I is associated
with severe intoxication and deaths in humans.[3]

25I was synthesized for biochemistry research to

map the brain's usage of the type 2A serotonin
receptor. 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.[4] The compound Clinical data
was subsequently investigated by a team at Purdue Routes of Buccal (sublabial),
University led by David Nichols.[5] administration sublingual, insufflated,

The carbon-11 labelled version of 25I-NBOMe, inhalation, intravenous,

[11C]Cimbi-5, was synthesized and validated as a intramuscular, rectal
radiotracer for positron emission tomography ATC code none
(PET) in Copenhagen.[6][7] Being the first 5-HT2A
Legal status
receptor full agonist PET radioligand, [11C]-CIMBI-5
shows promise as a more functional marker of these Legal status BR: Class F2 (Prohibited
receptors, particularly in their high affinity states.[6] psychotropics)[1]
DE: Anlage I (Authorized
Street and media nicknames for this drug are: "N-
Bomb", "Solaris", "Smiles", and "Wizard", although scientific use only)
the drug is frequently fraudulently sold as UK: Class A[2]
LSD.[8][9][10] US: Schedule I

Due to its physical effects and risk of overdose, EU: Controlled

there have been multiple deaths attributed to the Identifiers
drug. Its long term toxicity is unknown due to lack
of existing research. IUPAC name [show]
2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-metho
xyphenyl)methyl]ethanamine
Recreational use
CAS Number 919797-19-6 (https://comm
Although 25I-NBOMe was discovered in 2003, it onchemistry.cas.org/detail?
did not emerge as a common recreational drug until cas_rn=919797-19-6) 
2010, when it was first sold by vendors specializing
hydrochloride: 1043868-97-
in the supply of designer drugs.[11] In a slang
context, the name of the compound is often 8 (https://commonchemistr
shortened to "25I" or is simply called "N-Bomb".[12] y.cas.org/detail?cas_rn=104
According to a 2014 survey, 25I-NBOMe was the 3868-97-8)
most frequently used of the NBOMe series.[13] By
2013, case reports of 25I-NBOMe intoxication, with PubChem CID 10251906 (https://pubche
and without analytic confirmation of the drug in the m.ncbi.nlm.nih.gov/compo
body, were becoming increasingly common in the
und/10251906)
medical literature.[14]
ChemSpider 8427392 (https://www.che
25I-NBOMe is widely rumored to be orally inactive; mspider.com/Chemical-Stru
however, apparent overdoses have occurred via oral
cture.8427392.html) 
administration. Common routes of administration
UNII
include sublingual, buccal, and intranasal.[13] For 547KGL06IP (https://precisi
sublingual and buccal administration, 25I-NBOMe on.fda.gov/uniisearch/srs/u
is often applied to sheets of blotter paper of which nii/547KGL06IP)
small portions (tabs) are held in the mouth to allow hydrochloride: 0V30416N51
absorption through the oral mucosa.[15][16] There (https://precision.fda.gov/u
are reports of intravenous injection of 25I-NBOMe
niisearch/srs/unii/0V30416
solution and smoking the drug in powdered
N51)
form.[17][18]
ChEMBL ChEMBL1908863 (https://w
Due to its potency and much lower cost than so- ww.ebi.ac.uk/chembldb/ind
called classical or traditional psychedelics, 25I-
ex.php/compound/inspect/
NBOMe blotters are frequently misrepresented as,
ChEMBL1908863) 
or mistaken for, LSD blotters.[19] Even small
quantities of 25I-NBOMe can produce a large CompTox DTXSID20238808 (https://c
number of blotters. Vendors would import 25I- Dashboard
omptox.epa.gov/dashboar
NBOMe in bulk (e.g. 1 kg containers) and resell (EPA)
d/chemical/details/DTXSID
individual doses for a considerable profit.[16] 20238808)
Chemical and physical data
Dosage Formula C18H22INO3
25I-NBOMe is potent, being active in sub-milligram Molar mass 427.282 g·mol−1
doses. A common dose of the hydrochloride salt is 3D model Interactive image (https://c
600–1,200 μg. The UK Advisory Council on the (JSmol)
hemapps.stolaf.edu/jmol/j
Misuse of Drugs states that a common dose is
mol.php?model=COC1%3D
between 50 and 100  μg,[16] although other sources
indicate that these figures are incorrect; Erowid CC%3DCC%3DC1CNCCC2%
tentatively suggests that the threshold dosage for 3DCC%28%3DC%28C%3DC
humans is 50–250  μg, with a light dose between 2OC%29I%29OC)
200–600 μg, a common dose at 500–800 μg, and a SMILES [show]
strong dose at 700–1500 μg.[20] COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)I)
OC
At this level of potency, it is not possible to
accurately measure a single dose of 25I-NBOMe InChI [show]
powder without an analytical balance, and InChI=1S/C18H22INO3/c1-21-16-7-5-4-6-14
attempting to do so may put the user at significant (16)12-20-9-8-13-10-18(23-3)15(19)11-17
risk of overdose.[16] There is a high risk of overdose (13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3 
due to the small margin between a high-dose and an Key:ZFUOLNAKPBFDIJ-UHFFFAOYSA-N 
over-dose, which is not a risk with the similar drug    (what is this?)  (verify)
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.[21]

Effects
25I-NBOMe effects usually last 6–10 hours if taken sublingually, or buccally (between gum and
cheek).[18] When it is insufflated (snorted), effects usually last 4–6 hours.[18]

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.[13]

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)."[17]

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.[22]

Toxicity and harm potential

NBOMe compounds are often associated with life-threatening toxicity and death.[23][24] Studies on
NBOMe family of compounds demonstrated that the substance exhibit neurotoxic and cardiotoxic
activity.[25] Reports of autonomic dysfunction remains prevalent with NBOMe compounds, with
most individuals experiencing sympathomimetic toxicity such as vasoconstriction, hypertension
and tachycardia in addition to hallucinations.[26][27][28][29][30] Other symptoms of toxidrome of
include agitation or aggression, seizure, hyperthermia, diaphoresis, hypertonia, rhabdomyolysis,
and death.[26][30][24] Researchers report that NBOMe intoxication frequently display signs of
serotonin syndrome.[31] The likelihood of seizure is higher in NBOMes compared to other
psychedelics.[25]

NBOMe and NBOHs are regularly sold as LSD in blotter papers,[24][32] which have a bitter taste
and different safety profiles.[26][23] Despite high potency, recreational doses of LSD have only
produced low incidents of acute toxicity.[23] Fatalities involved in NBOMe intoxication suggest
that a significant number of individuals ingested the substance which they believed was LSD,[28]
and researchers report that "users familiar with LSD may have a false sense of security when
ingesting NBOMe inadvertently".[26] While most fatalities are due to the physical effects of the
drug, there have also been reports of death due to self-harm and suicide under the influence of the
substance.[33][34][26]

Given limited documentation of NBOMe consumption, the long-term effects of the substance
remain unknown.[26] NBOMe compounds are not active orally,[a] and are usually taken
sublingually.[36]: 3  When NBOMes are administered sublingually, numbness of the tongue and
mouth followed by a metallic chemical taste was observed, and researchers describe this physical
side effect as one of the main discriminants between NBOMe compounds and LSD.[37][38][39]

Neurotoxic and cardiotoxic actions

Many of the NBOMe compounds have high potency agonist activity at additional 5-HT receptors
and prolonged activation of 5-HT2B can cause cardiac valvulopathy in high doses and chronic
use.[24][29] 5-HT2B receptors have been strongly implicated in causing drug-induced valvular heart
disease.[40][41][42] The high affinity of NBOMe compounds for adrenergic α1 receptor has been
reported to contribute to the stimulant-type cardiovascular effects.[29]
In vitro studies, 25C-NBOMe has been shown to exhibit cytotoxicity on neuronal cell lines SH-
SY5Y, PC12, and SN471, and the compound was more potent than methamphetamine at reducing
the visibility of the respective cells; the neurotoxicity of the compound involves activation of
MAPK/ERK cascade and inhibition of Akt/PKB signaling pathway.[25] 25C-NBOMe, including the
other derivative 25D-NBOMe, reduced the visibility of cardiomyocytes H9c2 cells, and both
substances downregulated expression level of p21 (CDC24/RAC)-activated kinase 1 (PAK1), an
enzyme with documented cardiac protective effects.[25]

Preliminary studies on 25C-NBOMe have shown that the substance is toxic to development, heart
health, and brain health in zebrafish, rats, and Artemia salina, a common organism for studying
potential drug effects on humans, but more research is needed on the topic, the dosages, and if the
toxicology results apply to humans. Researchers of the study also recommended further
investigation of the drug's potential in damaging pregnant women and their fetus due to the
substance's damaging effects to development.[43][44]

Emergency treatment
At present, there are no specific antidotes for NBOMes, and all acute intoxication is managed by
symptomatic treatments, such as administration of benzodiazepines, antipsychotic drugs, and
antiarrhythmic agents, such as beta blockers; some emergency interventions are intended to
specifically treat rhabdomyolysis, which may lead to critical complications such as metabolic
acidosis and acute kidney injury.[25]

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 Erowid
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."[19] Several non-fatal overdoses requiring prolonged
hospitalization have also been reported.[16][14][17]

As of August 2015, 25I-NBOMe has reportedly led to at least 19 overdose deaths in the United
States.[12][45] In June 2012, two teens in Grand Forks, North Dakota and East Grand Forks,
Minnesota 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.[46] A 21-year-old man from Little Rock, Arkansas 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.[47] 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.[16] It is also cited in the death of a
21-year-old woman in August 2013[48] and the death of a 17-year-old in Minnesota in January
2014,[49] as well as the death of a 15-year old in Washington in September 2014.[50] 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.[51]
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.[52] A Sydney teenager jumped off a balcony to his death on June 5, 2013, while on
25I-NBOMe.[53]

25I-NBOMe has been linked to a major case on January 20, 2016, in Cork, Republic of Ireland,
which left six teenagers hospitalized, one of whom later died. At least one of the teenagers suffered
a cardiac arrest, according to reports, along with extreme internal bleeding.[54]

At least one suicide, and two attempted suicides leading to hospitalisation, have occurred while
under the effects of 25I-NBOMe.[55]

Pharmacology
25I-NBOMe acts as a highly potent full agonist for the human 5-
25I-NBOMe[56][57]
HT2A receptor,[56][58] with a dissociation constant (Kd) of
0.044 nM, making it some sixteen times the potency of 2C-I itself Receptor Kd (nM) ±
at this receptor. A radiolabelled form of 25I-NBOMe can be used 5-HT2A 0.044
for mapping the distribution of 5-HT2A receptors in the brain.[57]
5-HT2B 231 73
25I-NBOMe induces a head-twitch response in mice which is
5-HT2C 2
blocked completely by a selective 5-HT2A antagonist, suggesting
its psychedelic effects are mediated by 5-HT2A. This study 5-HT6 73 12
suggested that 25I-NBOMe is approximately 14-fold more potent μ-opioid 82 14
than 2C-I in-vivo.[59]
κ-opioid 288 50
While in-vitro studies showed that N-benzyl derivatives of 2C-I H1 189 35
were significantly increased in potency compared to 2C-I, the N-
benzyl derivatives of the related compound DOI were
inactive.[60]

25I-NBOMe also has weaker interactions with multiple other receptors. Kd values for interaction
with the following targets were greater than 500  nM: 5-HT1A, D3, H2, 5-HT1D, α1A adrenergic, δ
opioid, serotonin uptake transporter, 5-HT5A, 5-HT1B, D2, 5-HT7, D1, 5-HT3, 5-HT1E, D5,
muscarinic M1-M5, H3, and the dopamine uptake transporter.[57]

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.[16][14] 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.[16]

Analogues
25I-NBMD
Analogues and derivatives of 2C-I:
25I-NB34MD
25I-NB*: 25I-NBOH
25I-NBOMe (NBOMe-2CI)
25I-NBF 25I-NB3OMe
 25I-NB4OMe N-(2C-I) fentanyl[61]

N-(2C)-fentanyl:

Synthesis

25I-NBOMe is usually synthesised from 2C-I and 2-methoxybenzaldehyde, via reductive

alkylation. It can be done stepwise by first making the imine and then reducing the formed imine
with sodium borohydride, or by direct reaction with sodium triacetoxyborohydride.[4]

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.[62]

Canada

As of October 31, 2016; 25I-NBOMe is a controlled substance (Schedule III) in Canada.[63]

China

As of October 2015 25I-NBOMe is a controlled substance in China.[64]

European Union

In September 2014 the European Union implemented a ban of 25I-NBOMe in all its member
states.[65]

Israel

Israel banned 25I-NBOMe in 2013.[66]

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.[66]

United Kingdom
This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine
catch-all clause in the Misuse of Drugs Act 1971.[67]

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.[45] In November 2015, the temporary scheduling was extended for an additional
year[68] while permanent scheduling was arranged.[69] 25I-NBOMe, 25B-NBOMe and 25C-
NBOMe are currently Schedule 1 Substances according to 21 CFR 1308.11(d).[70]

Romania

In 2011, Romania banned all psychoactive substances.[71]

Serbia

25I-NBOMe was put on the list of prohibited substances in March 2015.[72]

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.[73]

Taiwan

Following the European rule from 2014, 25I-NBOMe was put in class 4 of prohibited
substances.[74]

Brazil

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

Notes
a. The potency of N-benzylphenethylamines via buccal, sublingual, or nasal absorption is
50-100 greater (by weight) than oral route compared to the parent 2C-x
compounds.[35] Researchers hypothesize the low oral metabolic stability of N-
benzylphenethylamines is likely causing the low bioavailability on the oral route,
although the metabolic profile of this compounds remains unpredictable; therefore
researchers state that the fatalities linked to these substances may partly be explained
by differences in the metabolism between individuals.[35]

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