To install click the Add extension button. That's it.

The source code for the WIKI 2 extension is being checked by specialists of the Mozilla Foundation, Google, and Apple. You could also do it yourself at any point in time.

How to transfigure the Wikipedia

Would you like Wikipedia to always look as professional and up-to-date? We have created a browser extension. It will enhance any encyclopedic page you visit with the magic of the WIKI 2 technology.

Try it — you can delete it anytime.

Install in 5 seconds
4,5
Kelly Slayton
Congratulations on this excellent venture… what a great idea!
Alexander Grigorievskiy
I use WIKI 2 every day and almost forgot how the original Wikipedia looks like.
Live Statistics
English Articles
Improved in 24 Hours
Added in 24 Hours
What we do. Every page goes through several hundred of perfecting techniques; in live mode. Quite the same Wikipedia. Just better.
Great Wikipedia has got greater.
.
Leo
Newton
Brights
Milds

25I-NBOH

From Wikipedia, the free encyclopedia

25I-NBOH
Legal status
Legal status
Identifiers
  • 2-((2-(4-Iodo-2,5-dimethoxyphenyl)ethylamino)methyl)phenol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H20INO3
Molar mass413.255 g·mol−1
3D model (JSmol)
  • Oc2ccccc2CNCCc(c(OC)cc1I)cc1OC
  • InChI=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 checkY
  • Key:FEUZHYRXGQTBRO-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

25I-NBOH (NBOH-2CI, Cimbi-27, 2-C-I-NBOH) is a derivative of the phenethylamine-derived hallucinogen 2C-I that was discovered in 2006 by a team at Purdue University.

Pharmacology

25I-NBOH acts as a potent agonist of the 5HT2A receptor,[2][3] with a Ki of 0.061 nM at the human 5HT2A receptor, similar to the better-known compound 25I-NBOMe, making it some twelve times the potency of 2C-I itself.

Although in vitro tests show this compound acts as an agonist, animal studies to confirm these findings have not been reported. While the N-benzyl derivatives of 2C-I had significantly increased binding to 5HT2A receptor fragments, compared to 2C-I, the N-benzyl derivatives of DOI were less active compared to DOI.[4]

25I-NBOH is notable as one of the most selective agonist ligands for the 5-HT2A receptor with an EC50 value of 0.074 nM with more than 400 times selectivity over the 5-HT2C receptor.[5]

Analytical chemistry

25I-NBOH is a labile molecule which fragments into 2C-I when analyzed by routine gas chromatography (GC) methods.[6] A specific method for reliable identification of 25I-NBOH using GC/MS has been reported, allowing forensic forces worldwide to correctly identify this compound.[7]

Legality

Sweden

The Riksdag added 25I-NBOH to Narcotic Drugs Punishments Act [sv] 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 listed as "25I-NBOH" and "2-([2-(4-jodo-2,5-dimetoxifenyl)etylamino]metyl)fenol".[8]

United Kingdom

This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.[9]

Analogues and derivatives

Analogues and derivatives of 2C-I:

25I-NB*:

N-(2C)-fentanyl:

  • N-(2C-I) fentanyl[10]

References

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, et al. (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): 681–93. doi:10.1007/s00259-010-1686-8. PMID 21174090. S2CID 12467684.
  3. ^ Silva ME, 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. Bibcode:2011JCAMD..25...51S. CiteSeerX 10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982. S2CID 3103050.
  4. ^ Braden MR, Parrish JC, Naylor JC, Nichols DE (December 2006). "Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists". Molecular Pharmacology. 70 (6): 1956–64. doi:10.1124/mol.106.028720. PMID 17000863. S2CID 15840304.
  5. ^ Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (March 2014). "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience. 5 (3): 243–9. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.
  6. ^ Arantes LC, Júnior EF, de Souza LF, Cardoso AC, Alcântara TL, Lião LM, et al. (2017). "2A receptor agonist identified in blotter paper seizures in Brazil". Forensic Toxicology. 35 (2): 408–414. doi:10.1007/s11419-017-0357-x. PMC 5486617. PMID 28706567.
  7. ^ Neto JC, Andrade AF, Lordeiro RA, Machado Y, Elie M, Júnior EF, Arantes LC (2017). "Preventing misidentification of 25I-NBOH as 2C-I on routine GC–MS analyses" (PDF). Forensic Toxicology. 35 (2): 415–420. doi:10.1007/s11419-017-0362-0. S2CID 32432586.
  8. ^ "Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkeme del, folkhälsa m.m." (PDF). Lakemedelsverket. Archived from the original (PDF) on 2017-10-30. Retrieved 2017-04-21.
  9. ^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
  10. ^ "Explore N-(2C-I)-Fentanyl | PiHKAL · info". isomerdesign.com.
This page was last edited on 4 February 2024, at 17:34
Basis of this page is in Wikipedia. Text is available under the CC BY-SA 3.0 Unported License. Non-text media are available under their specified licenses. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc. WIKI 2 is an independent company and has no affiliation with Wikimedia Foundation.
Contact WIKI 2
Introduction
Terms of Service
Privacy Policy