25I-NBOH

IdentifiersCAS NumberPubChem CIDChemSpiderUNIICompTox Dashboard (EPA)Chemical and physical dataFormulaC₁₇H₂₀INO₃Molar mass413.255 g·mol⁻¹3D model (JSmol) ^NY (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 5HT_2A receptor,^[2][3] with a K_i of 0.061 nM at the human 5HT_2A 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 5HT_2A 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-HT_2A receptor with an EC₅₀ value of 0.074 nM with more than 400 times selectivity over the 5-HT_2C 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

References