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
Molecular structure of 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 - 200 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.

25I-NBOH (also known as 2C-I-NBOH, NBOH-2CI, and Cimbi-27) is novel synthetic psychedelic substance of the phenethylamine chemical class that produces an array of visually-dominant and stimulating psychedelic effects when administered. 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

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This subjective effect breakdown is a stub.

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

You can help by expanding it.

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 injury or death.

Physical effects
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Visual effects
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Cognitive effects
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Multi-sensory effects
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Transpersonal effects
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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

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This toxicity and harm potential section is a stub.

As such, it may contain incomplete or even dangerously wrong information. You can help by expanding upon or correcting it.
We also recommend that you practice diligent independent research and the most thorough harm reduction practices when 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.[5]

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

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.

Legality

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This legality section is a stub.

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

  • United Kingdom - 25I-NBOH is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause.[7]
  • 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[8]

See also

External links

Forums

References

  1. 25I-NBOMe (2C-I-NBOMe) Fatalities / Deaths by Erowid | https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml
  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. (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. PMID 21174090. https://doi.org/10.1007/s00259-010-1686-8
  3. 3.0 3.1 Silva, M. E.; Heim, R.; Strasser, A.; Elz, S.; Dove, S. (2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor". Journal of Computer-aided Molecular Design. 25 (1): 51–66. PMID 21088982. https://doi.org/10.1007/s10822-010-9400-2
  4. Hansen, M.; Phonekeo, K.; Paine, J. S.; Leth-Petersen, S.; Begtrup, M.; Bräuner-Osborne, H.; Kristensen, J. L. (2014). "Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–9. PMC 3963123. PMID 24397362. https://doi.org/10.1021/cn400216u
  5. http://www.erowid.org/chemicals/2ci_nbome/2ci_nbome.shtml/
  6. 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
  7. 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
  8. https://lakemedelsverket.se/upload/lvfs/HSLF_FS_2015_12.pdf