25I-NBOH - PsychonautWiki

25I-NBOH

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25I-NBOH may result in severe injury or death.

While no deaths have been reported, it is likely that this compound shares a similar toxicity profile with 25I-NBOMe (which has been linked to multiple deaths).[1] It is strongly discouraged to take higher doses of this substance or to insufflate (snort) it. Please see this section for more details.

Summary sheet: 25I-NBOH
25I-NBOH
25I-NBOH.svg
Chemical Nomenclature
Common names 25i-NBOH, Cimbi-27
Substitutive name 2C-I-NBOH
Systematic name 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-hydroxyphenyl)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 - 900 µg
Strong 900 - 1400 µg
Heavy 25I-NBOH may be fatal at heavy doses.
Duration
Total 5 - 8 hours
Onset 15 - 60 minutes
Come up 30 - 90 minutes
Peak 2 - 3.5 hours
Offset 1.5 - 2.5 hours
After effects 3 - 12 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
Cannabis
Stimulants
Tramadol
Lithium


25I-NBOH (also known as 2C-I-NBOH, NBOH-2C-I, and Cimbi-27) is novel synthetic psychedelic substance of the phenethylamine class. It is a closely related analog of 25I-NBOMe and is reported to share most of its properties with the exception of a moderately reduced potency and a shorter duration.

The name 25I-NBOH, which short-hand for 2C-I-NBOH, is a derivative of the phenethylamine psychedelic 2C-I. It was first synthesized and documented in 2006 by a team at Purdue University led by David Nichols.[citation needed] 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).[2][3]

It is worth noting that compounds of the NBOH 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-NBOH in humans. It has no history of human use before being sold online as a designer drug in 2011.[citation needed] It is closely related to members of the 25x-NBOMe series, specifically 25I-NBOMe, which 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-NBOH or 2C-I-NBOH, is a serotonergic N-benzyl derivative of the substituted phenethylamine psychedelic known as 2C-I. 25I-NBOH 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-hydroxybenzyl (BOH) group. 25I-NBOH shares this 2-hydroxybenzyl substitution with other chemicals of the NBOH family. This NBOH addition is comprised of a hydroxy ether OH- bound to a benzene ring at R2.

Pharmacology

Further information: Serotonergic psychedelic

25I-NBOH has efficacy at the 5-HT2A receptor where it acts as a potent agonist.

This compound is pharmacologically unique when compared to other psychedelics due to the unusually high selectivity it displays for serotonin receptors. It is notable as one of the most selective agonist ligands for the 5-HT2A receptor with an EC50 value of 0.074 nM and more than 400x selectivity over the 5-HT2C receptor.[2][3] It has a Ki of 0.061 nM at the human 5HT2A receptor, similar to the better-known compound 25I-NBOMe, making it some twelve times as potent of 2C-I itself.[4]

However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.

Subjective effects

 
This subjective effects section is a stub.

As such, it is still in progress and may contain incomplete or wrong information.

You can help by expanding or correcting it.

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
 

Multi-sensory effects
 

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

 

This toxicity and harm potential section is a stub.

As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it.
Note: Always conduct independent research and use harm reduction practices if using this substance.

25I-NBOH is a relatively new substance, and little is known about its toxicity or interaction with other substances. It is assumed to pose similar acute health risks as 25I-NBOMe (see this section for more information). The LD50 has not yet been determined although it is likely to be potentially fatal at heavy dosages.

25I-NBOH's extreme potency means it should not be insufflated (snorted) as this method of administration has been associated with many deaths and hospitalizations with the closely related 25I-NBOMe.

Tolerance and addiction potential

25I-NBOH 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-NBOH 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-NBOH presents cross-tolerance with all psychedelics, meaning that after the consumption of 25I-NBOH all psychedelics will have a reduced effect.

Dangerous interactions

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.

Legal status

 

This legality section is a stub.

As such, it may contain incomplete or wrong information. You can help by expanding it.

  • Germany: 25I-NBOH is controlled under the NpSG (New Psychoactive Substances Act) as of November 26, 2016.[6][7] Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.[8]
  • Sweden: The Riksdag added 25I-NBOH to Narcotic Drugs Punishments Act under swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of August 18, 2015, published by Medical Products Agency (MPA) in regulation HSLF-FS 2015:12[9]
  • Switzerland: 25I-NBOH is a controlled substance specifically named under Verzeichnis E.[10]
  • United Kingdom: 25I-NBOH is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause.[11]

See also

External links

References

  1. Erowid 25I-NBOMe (2C-I-NBOMe) Vault : Fatalities / Deaths 
  2. 2.0 2.1 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-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–693. doi:10.1007/s00259-010-1686-8. ISSN 1619-7070. 
  3. 3.0 3.1 Silva, M. E., Heim, R., Strasser, A., Elz, S., Dove, S. (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. doi:10.1007/s10822-010-9400-2. ISSN 0920-654X. 
  4. Hansen, M., Phonekeo, K., Paine, J. S., Leth-Petersen, S., Begtrup, M., Bräuner-Osborne, H., Kristensen, J. L. (19 March 2014). "Synthesis and Structure–Activity Relationships of N -Benzyl Phenethylamines as 5-HT 2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–249. doi:10.1021/cn400216u. ISSN 1948-7193. 
  5. 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. ISSN 1556-9039. 
  6. "Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (PDF) (in German). Bundesanzeiger Verlag. Retrieved December 11, 2019. 
  7. "Anlage NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019. 
  8. "§ 4 NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019. 
  9. https://lakemedelsverket.se/upload/lvfs/HSLF_FS_2015_12.pdf
  10. "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020. 
  11. The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014, London: The Stationery Office Limited., 2014, retrieved 5 July 2017