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]
^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.
PMID21174090.
S2CID12467684.
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]
^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.
PMID21174090.
S2CID12467684.