Psychedelic Research Chemicals or RC Chems are new synthetic substances which are structurally similar to the original drug, while being functional analogs. Data on their effects limited due as they’re fairly new and do not have a lot of human consumption history.

Psychedelics are substances (natural or laboratory made) which cause profound changes in a one’s perceptions of reality. While under the influence of hallucinogens, users might hallcuniate visually and auditorily.

This is an Experimental Substance with little data. This is most likely because the substance is is not very old. Information is limite and incomplete.

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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.

Chemistry

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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Dose Chart

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

Duration Chart

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

Legal Status

Sources

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

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 to 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.