25I-NBOH

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25I-NBOH
Legal status
Legal status
Identifiers
  • 2-((2-(4-Iodo-2,5-dimethoxyphenyl)ethylamino)methyl)phenol
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

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

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

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
:

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. S2CID 12467684
    .
  3. S2CID 3103050
    .
  4. S2CID 15840304
    .
  5. PMID 24397362
    .
  6. PMID 28706567
    .
  7. 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". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
  10. ^ "Explore N-(2C-I)-Fentanyl | PiHKAL · info". isomerdesign.com.
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