25I-NBOH

Drugbox
IUPAC_name = 2-((2-(4-iodo-2,5-dimethoxyphenyl)ethylamino)methyl)phenol

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PubChem= 10001761
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C=17 | H=20 | I=1 | N=1 | O=3
molecular_weight = 413.249 g/mol
smiles = Oc2ccccc2CNCCc(c(OC)cc1I)cc1OC
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25I-NBOH or "N"-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane is a derivative of the phenethylamine derived hallucinogen 2C-I, discovered in 2006 by a team at Purdue University. It acts as a potent agonist for the 5HT_2A receptor with a Ki of 0.12nM at the human 5HT_2A receptor, making it some 5x the potency of 2C-I itself. "In vitro" tests showed this compound acted as an agonist but animal studies have not been reported. Interestingly while the "N"-benzyl derivatives of 2C-I were significantly increased in potency compared to 2C-I, the "N"-benzyl derivatives of DOI were inactive. [Braden MR, Parrish JC, Naylor JC, Nichols DE. Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent "N"-benzyl phenethylamine agonists. "Molecular Pharmacology". 2006 Dec;70(6):1956-64. PMID 17000863]

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