|Summary sheet: 25I-NBOMe|
|Molecular structure of 25I-NBOMe|
|Common names||25i-NBOMe, 25i, Cimbi-5|
|Routes of Administration|
25I-NBOMe (also known as 2C-I-NBOMe, Cimbi-5 and N-Bomb, although this term is used broadly to refer to the entire 25x-NBOMe family) is a novel psychedelic substance of the phenethylamine chemical class that produces an array of visually-dominant and stimulating psychedelic effects when administered.
The name 25I-NBOMe, which short-hand for 2C-I-NBOMe, is a derivative of the phenethylamine psychedelic 2C-I. It was first synthesized and documented in 2003 by Ralf Heim at the Free University of Berlin. It was further researched by a team at Purdue University led by David Nichols. It 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).
It is worth noting that compounds of the NBOMe family are not orally active and should be administered sublingually by placing and holding it into one's mouth and allowing it to absorb over a period of 15-25 minutes.
Extremely little is known about the pharmacological properties, metabolism, and toxicity of 25I-NBOMe in humans. It had no history of human use before being sold online as a designer drug in 2010.. It has been associated with many deaths and hospitalizations. Anecdotal reports suggest that this substance may be difficult to use safely due to its highly sensitive dose-response and unpredictable effects.
- 1 Chemistry
- 2 Pharmacology
- 3 Subjective effects
- 4 Toxicity and harm potential
- 5 Legal status
- 6 See also
- 7 External links
- 8 References
25I-NBOMe or 2C-I-NBOMe is a serotonergic N-benzyl derivative of the substituted phenethylamine psychedelic known as 2C-I. 25I-NBOMe is a substituted phenethylamine with methoxy groups CH3O- attached to carbons R2 and R5 as well as an iodine atom attached to carbon R4. It differs from 2C-I structurally through a substitution on the amine (NH2) with a 2-methoxybenzyl (BOMe) group. 25I-NBOMe shares this 2-methoxybenzyl substitution with other chemicals of the NBOMe family. This NBOMe addition contains a methoxy ether CH3O- bound to a benzene ring at R2.
25I-NBOMe has efficacy at the 5-HT2A receptor where it acts as an unusually potent and selective partial agonist. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.
Among psychedelics, this compound is considered to be pharmacologically unique in terms of the high potency, affinity, and selectivity with which it binds to the 5-HT2a receptor. Contrary to popular belief, it is not a "full agonist", although questions have been raised about how the effects it produces differ from other 5-HT2a partial agonists, which include the range of traditional psychedelics.
The Ki values of the following targets were greater than 500 Ki: 5-HT1A, D3, H2, 5-HT1D, α1A adrenergic, δ opioid, serotonin reuptake transporter, 5-HT5A, 5-HT1B, D2, 5-HT7, D1, 5-HT3, 5-HT1E, D5, muscarinic M1-M5, H3, and the dopamine reuptake transporter.
The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects should be taken with a grain of salt and will rarely (if ever) occur all at once, but heavier doses will increase the chances and are more likely to induce a full range of effects. Likewise, adverse effects become much more likely on higher doses and may include serious injury or death.
- Stimulation - In terms of its effects on the physical energy levels of the user, 25I-NBOMe is usually considered to be very energetic and stimulating. For most people, this substance induces a unique type of physical stimulation which can be described as feeling extremely energetic but in a way which does not force the tripper to move unless they genuinely choose to do so. For others, however, the stimulation can be quite uncontrollable, occasionally resulting in bodily shakes and a grinding of the teeth comparable to that of MDMA and traditional stimulants such as amphetamine.
- Perception of bodily lightness - In terms of the body’s perceived weight, this substance consistently leaves people feeling extremely light, often to the point of total weightlessness.
- Spontaneous physical sensations - The "body high" itself can be described as a mild, all-encompassing, soft but euphoric tingling sensation. This tingling sensation is also accompanied by spontaneous rushes of euphoria that become longer and more drawn out proportional to the dosage consumed.
- Mouth numbing - Assuming the substance has been taken sublingually, the very first physical effect which a person will notice immediately after sublingual absorption is a strong, unpleasant metallic chemical taste. This is accompanied by a very distinct feeling of general numbness of the tongue and mouth which can stay for up to an hour after the blotter paper has been consumed.
- Nausea - As the user begins to come up, nausea is not uncommon and can sometimes result in initial vomiting, although nausea usually disappears when the user has vomited or the trip fully set in. In comparison to other psychedelics such as psilocin, LSD, 2C-E and 2C-I, this could actually be considered very mild in its intensity.
- Temperature regulation suppression
- Abnormal heartbeat
- Increased heart rate
- Increased blood pressure
- Muscle contractions
- Muscle cramps
- Muscle tension
- Gustatory hallucinations
- Appetite suppression
- Stomach cramps
- Dry mouth
- Difficulty urinating or Frequent urination
- Restless legs
- Pupil dilation
- Visual acuity enhancement
- Colour enhancement
- Pattern recognition enhancement
- Magnification - At higher doses, users can experience a "fish-eye" effect, where magnification changes based on the direction the user is looking relative to the object.
- Drifting (melting, flowing, breathing and morphing) - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, static in appearance and unrealistic/cartoon-like in style.
- Colour shifting
- Colour replacement
- Colour tinting
- Depth perception distortions
- Perspective distortions
- Brightness alteration
- After images
- Symmetrical texture repetition
- Scenery slicing
The visual geometry produced by this substance is similar to LSD and can be comprehensively described as algorithmic in geometric style, intricate in complexity, fine and zoomed out in detail, fast and smooth in motion, structured in shape, colorful in scheme, glossy in color, sharp around the edges and equally angular as well as rounded across their corners. In comparison to other more commonly used psychedelics they can be described as significantly more intricate than the visual geometry found within 2C-I and most of the 2C-x family in general as well as completely on par with LSD, Psilocin and DMT at appropriately high dosages.
25I-NBOMe’s geometry leads reliably leads to Level 8A visual geometry with Level 8B remaining so far unconfirmed. It seems to consistently be able to build up in visual intensity when the user stares at a central point. This eventually envelops the visual field and creates the sensation that the tripper has broken through into a continuously shifting geometric landscape or structure with a vast sense of immersive physical size attributed to it.
25I-NBOMe is capable of producing a full range of hallucinatory states within the level 1 - 3 range extremely consistently. However, level 4 hallucinatory breakthroughs are reported but very different and inconsistent in comparison to other more commonly used psychedelics such as psilocin, 2C-E and DMT.
These effects include:
- Machinescapes - This component is an uncommon effect that typically only occurs at very strong to heavy doses. It also tends to be accompanied by overwhelming if not dangerous physical and cognitive effects.
- Internal hallucinations - (settings, sceneries, and landscapes; alterations in perspective and scenarios and plots). These are more common within dark environments and can be described as lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
The cognitive effects of 25I-NBOMe are described by many as notably light in comparison to the classical psychedelics. It is not uncommon for people to report feeling that their thought stream has maintained general normality in its specific style throughout low to moderate dosages. At high dosages, however, strong to overwhelming cognitive alterations become present, which can lead to states of confusion, amnesia, and general sensory overload.
The most prominent of these cognitive effects generally include:
- Analysis enhancement - This effect is generally only present at low doses.
- Thought acceleration and Thought deceleration - Although one of 25i-NBOME's effects is thought acceleration, the opposite may occur at higher doses.
- Conceptual thinking - This effect is considered to be very mild compared to traditional psychedlics.
- Anxiety & Paranoia - This effect seems to occur more readily than other psychedelics, perhaps due to its very prominent stimulating properties
- Feelings of impending doom - This is generally only experienced during the comedown period or if one has taken a large amount of the substance.
- Empathy, affection, and sociability enhancement - The entactogenic effects range from mild to powerful, but are inconsistently manifested. Entactogenic effects for people who try this substance usually become prominent in the presence of others. These feelings of increased sociability, love and empathy do not seem to be quite as strong or profound as those found within other entactogens (such as MDMA, 2C-B and AMT)
- Memory suppression
- Novelty enhancement
- Immersion enhancement
- Emotion enhancement
- Increased sense of humor
- Increased music appreciation
- Personal bias suppression
- Increased libido
- Time distortion
- Dosage independent intensity - While the reasons for this are not understood, many reports suggest that this substance can produce unexpectedly strong or weak effects even when taken at the seemingly same dose in an unpredictable manner. This may contribute to the relative risk it is poses compared to most other psychedelics.
- Synaesthesia - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dosage can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states.
- While they are occasionally reported, the transpersonal effects produced by this substance seem to be significantly less consistent and reproducible than other psychedelics, which perhaps corresponds with the notably mild changes to one's perceptual and cognitive processes.
Anecdotal reports which describe the effects of this compound within our experience index include:
- Experience:1000ug / 1 tab - No sense of enlightenment but absolutely breath taking visuals
- Experience:Becoming a god with my boyfriend
- Experience:Unknown dosage - Ego death and becoming one with a singular entity
- Experience:Unknown dosage / 1 tabs - Prolonged unity and messiah syndrome at school
- Experience:Unknown dosage / 3 tabs - Ego death and a total break through in the snow
Additional experience reports can be found here:
Toxicity and harm potential
25I-NBOMe is a relatively new substance, and little is known about its pharmacological risks or its interaction with other substances. The LD50 has not yet been determined although it is potentially fatal at heavy dosages. PsychonautWiki advises that due to 25I-NBOMe's extreme potency it should not be insufflated as this method of administration appears to have led to several deaths in the past year.
This substance came to media attention in early 2012 after a cluster of seven non-fatal overdoses with the drug were reported in or around Richmond, Virginia. As of May 2013, 25I-NBOMe has reportedly led to five overdose deaths in the United States. 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.
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 usually do not test for the presence of research chemicals.
A man in Australia died from injuries sustained by running into trees and power poles while intoxicated by 25I-NBOMe.
A Brazilian 16-year-old died from overdose in April 2016.
The addition of 5-HTP can greatly increase the effects of 25i-NBOME and should be avoided.
It is strongly recommended that one use harm reduction practices when using this substance.
Tolerance and addiction potential
25I-NBOMe is not habit-forming and the desire to use it can actually decrease with use. It is most often self-regulating.
Tolerance to the effects of 25I-NBOMe is built almost immediately after ingestion. After that, it takes about 1 week for the tolerance to be reduced to half and 2 weeks to be back at baseline (in the absence of further consumption). 25I-NBOMe presents cross-tolerance with all psychedelics, meaning that after the consumption of 25I-NBOMe all psychedelics will have a reduced effect.
This dangerous interactions section is a stub.
As such, it may contain incomplete or invalid information. You can help by expanding upon or correcting it.
Although many psychoactive substances are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.
- Tramadol - Tramadol lowers the seizure threshold and psychedelics may act as triggers for seizures, particularly in those who are predisposed to them.
- Stimulants - Stimulants affect many parts of the brain. Combined with psychedelics, stimulation can turn into uncontrollable anxiety, panic, thought loops and paranoia. This interaction may cause elevated risk of psychosis.
- Lithium - Lithium is often used as treatment for bipolar disorder. It may possibly cause elevated risk of seizures and psychosis due to its glutaminergic and GABAergic effects.
- Australia: Possession, production and sale is illegal.
- Brazil - Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.
- Canada: 25I-NBOMe would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.
- China - As of October 2015 25I-NBOMe is a controlled substance in China.
- Germany - Possession, production and sale is illegal.
- Israel: The drug was banned in 2012.
- Latvia: 25I-NBOMe is a Schedule I controlled substance.
- New Zealand: 25I-NBOMe is a Schedule 2 controlled substance in New Zealand.
- Romania: In 2011, Romania banned all psychoactive substances, no matter what they really are.
- Russia: Possession, production and sale is illegal.
- Sweden: 25I-NBOMe is classed as Schedule I.
- United Kingdom - 25I-NBOMe is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause.
- United States: On Nov 15, 2013, the DEA added 25I-NBOMe to Schedule I using their emergency scheduling powers, making it "temporarily" in Schedule I for 2 years.
- 25I-NBOMe (2C-I-NBOMe) Fatalities / Deaths by Erowid | https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml
- "Fatalities / Deaths". Erowid. April 26 2013. Retrieved 7 May 2013. | http://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml
- 25I-NBOMe (2C-I-NBOMe) Fatalities / Deaths by Erowid | https://www.erowid.org/chemicals/nbome/nbome_death.shtml
- Ralf Heim PhD. (2010-02-28) "Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts." | http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 (in German). diss.fu-berlin.de. Retrieved 2013-05-10.
- Michael Robert Braden PhD. (2007). "Towards a biophysical understanding of hallucinogen action." | http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 Purdue University. Retrieved 2012-08-08.
- Ettrup, A. E. A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging 38 (4): 681–693. (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/21174090
- High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/18468904
- Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/21174090
- "Fatalities / Deaths". Erowid. April 26, 2013. Retrieved 7 May 2013. | http://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml
- "Kids overdosing on new drug. Laura Geller, WWBT NBC12, Feb 18, 2012 | http://www.nbc12.com/story/16964534/kids-overdosing-on-new-drug
- New street drug causing concern among medics. Vanessa Araiza, WBRC, Feb 28, 2012, | http://www.wsfa.com/story/16977573/new-street-drug-causing-concern-among-medics
- New drug N-bomb hits the street, terrifying parents, troubling cops | http://www.nydailynews.com/news/national/new-synthetic-hallucinogen-n-bomb-killing-users-cops-article-1.1336327
- Breaking Bad: Digital Drug Sales, Analog Drug Deaths. Craig Malisow, Houston Press, March 13, 2013 | http://www.houstonpress.com/2013-03-14/news/motion-research-charles-carlton/
- 21-year-old dies after one drop of new synthetic drug at Voodoo Fest. Naomi Martin, NOLA, November 1, 2012 | http://www.nola.com/crime/index.ssf/2012/11/21-year-old_dies_after_one_dro.html#incart_m-rpt-2/
- New hallucinogenic drug 25B-NBOMe and 25I-NBOMe led to South Australian man's bizarre death | http://www.adelaidenow.com.au/news/south-australia/new-hallucinogenic-drug-25b-nbome-and-25i-nbome-led-to-south-australian-mans-bizarre-death/story-e6frea83-1226472672220/
- Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of medical toxicology, 5(2), 63-67. doi:10.1007/BF03161089
- Controlled Drugs and Substances Act (S.C. 1996, c. 19) |http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-12.html#h-28
- http://www.sfda.gov.cn/WS01/CL0056/130753.html | 关于印发《非药用类麻醉药品和精神药品列管办法》的通知
- BtMG Anlage I | https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html
- Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (2,5-Dimetoksifeniletānamīni) | http://likumi.lv/doc.php?id=121086
- Läkemedelsverkets författningssamling - http://www.lakemedelsverket.se/upload/lvfs/LVFS_2013-15.pdf
- United Kingdom. (2014). Misuse of Drugs Act 1971 (S.I. 2014/1106). London: The Stationery Office Limited. Retrieved July 5, 2017, from http://www.legislation.gov.uk/uksi/2014/1106/made