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25I-NBOMe
Systematic (IUPAC) name
2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
Identifiers
CAS number 919797-19-6
1043868-97-8 (hydrochloride)
ATC code  ?
PubChem 10251906
Chemical data
Formula C 18H22INO3  
Mol. mass 427.277 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

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] It acts as a potent agonist for the 5HT2A receptor with a Ki of 0.044nM at the human 5HT2A receptor, making it some sixteen times 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.[3] Anecdotal reports from human users suggest 25I-NBOMe to be an active hallucinogen at a dose of as little as 500mcg, making it a similar potency to other phenethylamine derived hallucinogens such as bromo-dragonfly.

See also

References

  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.
  3. ^ 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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