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Systematic (IUPAC) name
CAS Number 919797-19-6
1043868-97-8 (hydrochloride)
ATC code none
PubChem CID 10251906
Chemical data
Formula C18H22INO3
Molar mass 427.277 g/mol[[Script error: No such module "String".]]
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25I-NBOMe (NBOMe-2C-I, BOM-CI or N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane) is a derivative of the phenethylamine hallucinogen 2C-I, discovered in 2004 by Ralf Heim at the Free University of Berlin,[1] and subsequently investigated in more detail by a team at Purdue University led by David Nichols.[2]

25I-NBOMe acts as a highly potent agonist for the human 5-HT2A receptor with a Ki of 0.044 nM, making it some sixteen times the potency of 2C-I itself, and a radiolabelled form of 25I-NBOMe can be used for mapping the distribution of 5-HT2A receptors in the brain.[3] 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.[4]

Anecdotal reports from human users suggest 25I-NBOMe to be an active hallucinogen at a dose of as little as 500 mcg, making it a similar potency to other phenethylamine derived hallucinogens such as bromo-dragonfly.[citation needed]

See also


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  1. Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)
  2. Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.
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  4. 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