25I-NBOH

25I-NBOH

25I-NBOH

Psychoactive Research chemicals are new synthetic substances that are structurally similar to the original drug, while being functional analogs. Research on the effects of, and treatment for, abuse of these drugs is limited due to the fact that they’re fairly new and have avoided mainstream notice. Research chemicals do not have a lot of human consumption data, and thus harm-reduction and special care should be taken if choosing to ingest them.

Psychedelics are drugs which cause profound changes in a one’s perceptions of reality, otherwise known as hallucinations. While under the influence of hallucinogens, users might see images, hear sounds or feel sensations. These chemicals offer some of the most intense psychological experiences and care should be taken when ingesting them.

Experimental drugs have extremely limited human consumption data. There is not enough reliable information about this substance. This is most likely because the substance is is not very old. Information on these substances is limite and incomplete. Please be cautioned. Always practice harm reduction.

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Description

25I-NBOH

Also known as:

  • 2-({[2-(4-Iod-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol[German][ACD/IUPAC Name]
  • 2-({[2-(4-Iodo-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol[ACD/IUPAC Name]
  • 2-({[2-(4-Iodo-2,5-diméthoxyphényl)éthyl]amino}méthyl)phénol[French][ACD/IUPAC Name]
  • 25I-NBOH
  • Phenol, 2-[[[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]amino]methyl]-[ACD/Index Name]

A phenethylamine psychedelic and stimulant derivative of 2C-I, this compound is related and has similar effects to 25i-NBOMe. It is significantly more potent than 2C-I but less potent than 25i-NBOMe. Overdoses of NBOH compounds may cause dangerous vasoconstriction. May induce uncomfortable body load.

Summary

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.

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 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. 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.

History

Chemistry

25I-NBOH

25I-NBOH

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.

Common Name25I-NBOH
Systematic name25I-NBOH
FormulaC_{17}H_{20}INO_{3}
SMILESIc1cc(OC)c(cc1OC)CCNCc2ccccc2O
Std. InChiInChI=1S/C17H20INO3/c1-21-16-10-14(18)17(22-2)9-12(16)7-8-19-11-13-5-3-4-6-15(13)20/h3-6,9-10,19-20H,7-8,11H2,1-2H3
Std. InChiKeyFEUZHYRXGQTBRO-UHFFFAOYSA-N
Avg. Mass413.2501 Da
Molecular Weight413.2501
Monoisotopic Mass413.048767 Da
Nominal Mass413
ChemSpider ID8177342

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Dosing Guide

Oral
Threshold166ug-416ug
Light416ug-766ug
Common800-1400ug
Strong1400ug-2000ug+

Duration

25I-NBOH Duration Data
Onset20-40 minutes
Duration5-10 hours
After-effects1-12 hours

Interactions and Synergies

There are no existing interaction or synergy data for this drug.

General Information

Experiences
Oral
Vaporization
Come up
Dosage
EffectsEuphoria, empathy, insight, brightened colour, Closed/Open eye visuals, enhanced tactile sensation, mental/physical stimulation, decreased appetite, pupil dilation, restlessness, change in perception, ego softening, sweating/chills, muscle tension, confusion, insomnia.
After Effects
AvoidOther psychedelics, stimulants, and double dosing.
Warning
Risks
Test Kits
Marguis Test Result
Tolerance
Detection
Half-life
Advice
Note
Note 2:
Note 3:

Effects

Pharmacological Effects

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

Subjective Effects

Physical Effects

Psychological Effects

The cognitive effects of 25I-NBOH 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:

Visual Effects

Enhancements

Suppressions

Distortions

Geometry

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-NBOH’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.

Hallucinatory states

25I-NBOH 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:

Auditory Effects

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. 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

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.

Legal Status


References

  1. 25I-NBOMe (2C-I-NBOMe) Fatalities / Deaths by Erowid | https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml
  2. 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. 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. :10.1007/BF03161089.  1556-9039.
  7. "Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (PDF) (in German). Bundesanzeiger Verlag. Retrieved December 11, 2019.
  8. "Anlage NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019.
  9. "§ 4 NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019.
  10. https://lakemedelsverket.se/upload/lvfs/HSLF_FS_2015_12.pdf
  11. 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

Sources

Information made possible with:

  1. PsychonautWiki is a community-driven online encyclopedia that aims to document the field of psychonautics in a comprehensive, scientifically-grounded manner.
  2. Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
  3. PubChem National Center for Bio Informatics
  4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
  5. Wikipedia

Additional APIs were used to construct this information. Thanks for ChemSpider, NCBI, PubChem etc.

Data is constantly updated so please check back later to see if there is any more available information on this substance.