25I-NBOMe - PsychonautWiki

25I-NBOMe

(Redirected from 2C-I-NBOMe)


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25I-NBOMe can be fatal at heavy doses.[1]

It is strongly discouraged to take large amounts of this substance or to insufflate (snort) it. Please see this section for more details.

Summary sheet: 25I-NBOMe
25I-NBOMe
25I-NBOMe.svg
Chemical Nomenclature
Common names 25i-NBOMe, 25i, Cimbi-5
Substitutive name 2C-I-NBOMe
Systematic name 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
Class Membership
Psychoactive class Psychedelic
Chemical class Phenethylamine
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.





⇣ Sublingual
Dosage
Threshold 50 µg
Light 200 - 500 µg
Common 500 - 700 µg
Strong 700 - 1000 µg
Heavy 25I-NBOMe can be fatal at heavy doses.[1]
Duration
Total 6 - 10 hours
Onset 15 - 120 minutes
Come up 30 - 120 minutes
Peak 2 - 4 hours
Offset 1 - 4 hours
After effects 3 - 6 days
⇣ Insufflated
Dosage
Threshold 50 µg
Light 200 - 500 µg
Common 500 - 700 µg
Strong 700+ µg
Heavy 25I-NBOMe can be fatal at heavy doses.[2]
Duration
Total 4 - 6 hours
Onset 5 - 10 minutes
Come up 10 - 30 minutes
Peak 60 - 120 minutes
Offset 120 - 180 minutes
After effects 1 - 7 days






DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.

Interactions
2C-T-X
5-MeO-xxt
Caffeine
Cannabis
DOx
MAOIs
MDMA
MXE
Amphetamines
aMT
Cocaine
DXM
Tramadol
Lithium


25I-NBOMe (also known as 2C-I-NBOMe, NBOMe-2C-I, Cimbi-5, Smiles, and one of many drugs referred to as N-Bomb) 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.[3] It was further researched by a team at Purdue University led by David Nichols.[4] 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).[5][6]

It is worth noting that compounds of the NBOMe family (any of which could be referred to as "N-Bomb", especially 25I-NBOMe and 25N-NBOMe) 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.[citation needed]. 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.

Chemistry

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.

Pharmacology

Further information: Serotonergic psychedelic

25I-NBOMe has efficacy at the 5-HT2A receptor where it acts as a Full agonist.[5] 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.[5] Contrary to popular belief, it is not a "full agonist"[citation needed], 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.[7]

Ki-values[5][7]
Receptor Ki (nM) ±
5-HT2A 0.044
5-HT2C 2
5-HT6 73 12
μ-opioid 82 14
H1 189 35
5-HT2B 231 73
κ-opioid 288 50

Subjective effects

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.


Physical effects
 

Visual effects
 

Cognitive effects
 

Auditory effects
 

Multi-sensory effects
 

    • 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.[citation needed] 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.

Transpersonal effects
 

Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include:

Additional experience reports can be found here:

Toxicity and harm potential

Further information: Research chemicals § Toxicity and harm potential, and Responsible use § Hallucinogens

Short-term as well as long-term damage of NBOMes have been occasionally tied to serious physical and mental problems on seemingly random people, including memory and speech difficulties, heart problems, HPPD and in some cases Anxiety and PTSD, from particularly difficult experiences.

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.[1] 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.[8][9] As of May 2013, 25I-NBOMe has reportedly led to five overdose deaths in the United States.[10] 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.[11]

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.[12]

A man in Australia died from injuries sustained by running into trees and power poles while intoxicated by 25I-NBOMe.[13]

A Brazilian 16-year-old died from overdose in April 2016.[citation needed]

The addition of 5-HTP can greatly increase the effects of 25i-NBOME and should be avoided.[citation needed]

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.

Overdose

Due to the very high potency and seemingly unpredictable effects the margin between a normal and an overdose of NBOMe compounds is extremely small when compared to many other substances. The exact toxic dose is unclear since it seems to depend a lot on personal physiology, rather than predominantly dose. However, various anecdotal reports suggest that dangerous side effects begin to appear when exceeding 1000 μg and it possibly becoming lethal for the more sensitive people at roughly 2000 μg. Reports of other people surviving much higher doses, sometimes even without any major side effects have been documented as well.

There is also the uncertainty of dosage on blotter paper since it is rather difficult to lay such an exact dosage. Insufflating, vaporizing or drinking tinctures of this substance is highly discouraged because of this and has been tied to many documented deaths[1][14][2]. One study found that 25I‐NBOMe and 25C‐NBOMe blotter papers contained 'hotspots' with higher quantities of the drug, implying an inherent risk of overdosing.[15]

The overdose effects of NBOMes are typically a dangerously high heart rate, blood pressure, hyperthermia and significant vasoconstriction[16][17] also accompanied by confusion, delusions, panic attacks, aggressive behavior, numbness or pain, amnesia and often seizures. The risks in an overdose include anything from organ failure to cardiac arrest and death[citation needed]. There are also multiple reports of people lethally injuring themselves or falling to death[18][19]. Benzodiazepines or antipsychotics can help with the psychological effects during an overdose although medical attention should always be called in even a possible overdose of 25I-NBOMe.

Dangerous interactions

 

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.

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit. Due to the highly unpredictable nature of the NBOMe series, it is generally advised to avoid mixing them with other psychoactive substances.

  • 2C-T-X - The 2C-T-X phenethylamines can be unpredictable in their interactions and the NBOMes are known to be unpredictable even alone. As a result, this combination should be avoided.
  • 5-MeO-xxt - The 5-MeO tryptamines can be unpredictable in their interactions and the NBOMes are known to be unpredictable even alone. As a result, this combination should be avoided.
  • Amphetamines - Amphetamines and NBOMes both provide considerable stimulation. When combined they can result in tachycardia, hypertension, vasoconstriction and, in extreme cases, heart failure. The anxiogenic and focusing effects of stimulants are also not good in combination with psychedelics as they can lead to unpleasant thought loops. NBOMes are known to cause seizures and stimulants can increase this risk.
  • aMT
  • Caffeine - Caffeine can bring out the natural stimulation from psychedelic drugs to make it uncomfortable. High doses can cause anxiety which is hard to handle while tripping.
  • Cannabis - Cannabis has an unexpectedly strong and unpredictable synergy with the effects of psychedelics. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid over intake.
  • Cocaine - Cocaine and NBOMes both provide considerable stimulation. When combined they can result in severe vasoconstriction, tachycardia, hypertension, and in extreme cases heart failure.
  • DOx
  • DXM
  • Lithium - Lithium is commonly prescribed in the treatment of [https://en.wikipedia.org/wiki/Bipolar_disorder bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged.
  • MAOIs - MAO-B inhibitors can increase the potency and duration of phenethylamines unpredictably.
  • MDMA
  • MXE - As an NMDA antagonist, MXE potentiates NBOMes which can be unpleasantly intense.
  • Tramadol - Tramadol is well known to lower seizure threshold and NBOMes have also shown a tendency to cause severe seizures

Legal status

In September 2014, the European Council decided that 25I-NBOMe shall be subjected by the Member States to control measures and criminal penalties by October 2, 2015.[20]

  • Australia: Possession, production and sale is illegal.[citation needed]
  • Austria: Since June 26, 2019, 25I-NBOMe is illegal to possess, produce and sell under the SMG. (Suchtmittelgesetz Österreich)[21]
  • Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[22]
  • Canada: 25I-NBOMe would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.[23]
  • China: As of October 2015 25I-NBOMe is a controlled substance in China.[24]
  • Denmark: 25I-NBOMe is controlled by the generic classification of phenethylamines in the Executive Order on Euphoriant Substances.[25]
  • Germany: 25I-NBOMe is controlled under Anlage I BtMG (Narcotics Act, Schedule I)[26] as of December 13, 2014.[27] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[28]
  • Finland: 25I-NBOMe is controlled under the Medicines Act (395/87) as of March 15, 2013.[25]
  • Hungary: 25I-NBOMe falls within the generic definition of phenethylamines in Schedule C of Government Decree 66/2012.[25]
  • Israel: The drug was banned in 2012.[29]
  • Italy: In Italy 25I-NBOMe is a Schedule 1 controlled substance, meaning it's illegal in this state.[30]
  • Japan: 25I-NBOMe is a narcotic drug in Japan effective November 1st, 2015.[31]
  • Latvia: 25I-NBOMe is a Schedule I controlled substance.[32]
  • New Zealand: 25I-NBOMe is a Schedule 2 controlled substance in New Zealand.[33]
  • Norway: 25I-NBOMe is controlled by the generic scheduling of phenethylamines as of February 14, 2013.[25]
  • Poland: 25I-NBOMe falls under the definition of a ‘substitution drug’ under the Act on Counteracting Drug Addiction and the Act on State Sanitary Inspection, 2010. As such its marketing and production is penalised with a fine (administrative sanctions).[25]
  • Romania: In 2011, Romania banned all psychoactive substances,[34] no matter what they really are.[35]
  • Russia: Possession, production and sale is illegal.[citation needed]
  • Slovenia: 25I-NBOMe was included in a Decree amending the classification of illicit drugs (Official Gazette of RS No. 62/2013).[25]
  • Sweden: 25I-NBOMe is classed as Schedule I.[36]
  • Switzerland: 25I-NBOMe is a controlled substance specifically named under Verzeichnis D.[37]
  • United Kingdom: 25I-NBOMe is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause.[38]
  • 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.[39]

See also

External links

Discussion

References

  1. ↑ 1.0 1.1 1.2 1.3 Erowid 25I-NBOMe (2C-I-NBOMe) Vault : Fatalities / Deaths 
  2. ↑ 2.0 2.1 Erowid NBOMe (Other or Unknown NBOMe-Compound) Vault : Fatalities / Deaths 
  3. ↑ Heim, R. (2004). "Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2 -Methoxybenzyl-Partialstruktur: Entwicklung eines neuen Struktur-Wirkungskonzepts". doi:10.17169/refubium-16193. Retrieved 10 May 2013. 
  4. ↑ Braden, M. R. (1 January 2007). "Towards a biophysical understanding of hallucinogen action". Theses and Dissertations Available from ProQuest: 1–176. Retrieved 8 August 2012. 
  5. ↑ 5.0 5.1 5.2 5.3 Ettrup, A., Hansen, M., Santini, M. A., Paine, J., Gillings, N., Palner, M., Lehel, S., Herth, M. M., Madsen, J., Kristensen, J., Begtrup, M., Knudsen, G. M. (April 2011). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–693. doi:10.1007/s00259-010-1686-8. ISSN 1619-7089. 
  6. ↑ 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. ISBN 9788792719003. 
  7. ↑ 7.0 7.1 Nichols, D. E., Frescas, S. P., Chemel, B. R., Rehder, K. S., Zhong, D., Lewin, A. H. (1 June 2008). "High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand". Bioorganic & Medicinal Chemistry. 16 (11): 6116–6123. doi:10.1016/j.bmc.2008.04.050. ISSN 1464-3391. 
  8. ↑ Geller, L. (2012), Kids overdosing on new drug, WWBT NBC12 
  9. ↑ 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
  10. ↑ {{Citation | title=New drug N-bomb hits the street, terrifying parents, troubling cops | url=https://www.nydailynews.com/news/national/new-synthetic-hallucinogen-n-bomb-killing-users-cops-article-1.1336327
  11. ↑ 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/
  12. ↑ Martin, N. (2012), 21-year-old dies after one drop of new synthetic drug at Voodoo Fest, NOLA 
  13. ↑ 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/
  14. ↑ Erowid 2C-C-NBOMe (25C-NBOMe) Vault : Fatalities / Deaths 
  15. ↑ Lützen, E., Holtkamp, M., Stamme, I., Schmid, R., Sperling, M., Pütz, M., Karst, U. (April 2020). "Multimodal imaging of hallucinogens 25C‐ and 25I‐NBOMe on blotter papers". Drug Testing and Analysis. 12 (4): 465–471. doi:10.1002/dta.2751. ISSN 1942-7603. 
  16. ↑ Marchi, N. C., Scherer, J. N., Fara, L. S., Remy, L., Ornel, R., Reis, M., Zamboni, A., Paim, M., Fiorentin, T. R., Wayhs, C. A. Y., Von Diemen, L., Pechansky, F., Kessler, F. H. P., Limberger, R. P. (1 March 2019). "Clinical and Toxicological Profile of NBOMes: A Systematic Review". Psychosomatics. 60 (2): 129–138. doi:10.1016/j.psym.2018.11.002. ISSN 0033-3182. 
  17. ↑ Yoon, K. S., Yun, J., Kim, Y.-H., Shin, J., Kim, S. J., Seo, J.-W., Hyun, S.-A., Suh, S. K., Cha, H. J. (1 April 2019). "2-(2,5-Dimethoxy-4-methylphenyl)-N-(2-methoxybenzyl)ethanamine (25D-NBOMe) and N-(2-methoxybenzyl)-2,5-dimethoxy-4-chlorophenethylamine (25C-NBOMe) induce adverse cardiac effects in vitro and in vivo". Toxicology Letters. 304: 50–57. doi:10.1016/j.toxlet.2019.01.004. ISSN 0378-4274. 
  18. ↑ https://psychonautwiki.org/wiki/File:Nbome_death_news_i2013e0190_disp.jpg
  19. ↑ https://psychonautwiki.org/wiki/File:Nbome_death_news_i2013e0191_disp.jpg
  20. ↑ "Council Implementing Decision on subjecting 25I-NBOMe, AH-7921, MDPV and methoxetamine to control measures". Official Journal of the European Union. Office for Official Publications of the European Communites (published October 1, 2014). September 25, 2014. pp. 22–26. OCLC 52224955. L 287. 
  21. ↑ https://www.ris.bka.gv.at/Dokumente/BgblAuth/BGBLA_2019_II_167/BGBLA_2019_II_167.pdfsig
  22. ↑ http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
  23. ↑ Branch, L. S. (2022), Consolidated federal laws of Canada, Controlled Drugs and Substances Act 
  24. ↑ 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
  25. ↑ 25.0 25.1 25.2 25.3 25.4 25.5 "25I-NBOMe: EMCDDA–Europol Joint Report on a new psychoactive substance: 25I-NBOMe (4-iodo-2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine)" (PDF). European Monitoring Centre for Drugs and Drug Addiction. 2014. doi:10.2810/27828. ISBN 978-92-9168-682-7. ISSN 1977-7868. Retrieved February 18, 2020. 
  26. ↑ "Anlage I BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019. 
  27. ↑ "Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (PDF) (in German). Bundesanzeiger Verlag. Retrieved December 11, 2019. 
  28. ↑ "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019. 
  29. ↑ http://www.health.gov.il/LegislationLibrary/25574413.pdf
  30. ↑ Tabella 1 Stupefacenti dello Stato Italiano |http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf
  31. ↑ 新たに４物質を麻薬に指定し、規制の強化を図ります ｜報道発表資料｜厚生労働省, 厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)] 
  32. ↑ Zaudējis spēku - Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem 
  33. ↑ Misuse of Drugs Act 1975 No 116 (as at 07 December 2021), Public Act – New Zealand Legislation 
  34. ↑ Takács, I. G. (2013), Colored City: Recreational drug use in Belgrade 
  35. ↑ http://www.dreptonline.ro/legislatie/legea_194_2011_comba
  36. ↑ Läkemedelsverkets författningssamling (PDF) 
  37. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020. 
  38. ↑ The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 
  39. ↑ http://www.justice.gov/dea/divisions/hq/2013/hq111513.shtml


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