25I-NBOMe

25I-NBOMe
25I-NBOMe
Systematic (IUPAC) name
2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 919797-19-6
1043868-97-8 (hydrochloride)
ATC code None
PubChem CID 10251906
ChemSpider 8427392 YesY
Chemical data
Formula C18H22INO3 
Mol. mass 427.277 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

25I-NBOMe (NBOMe-2C-I, BOM-CI, Cimbi-5) is a derivative of the phenethylamine hallucinogen 2C-I, discovered in 2003 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,[3][4] 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.[5][6] In vitro tests showed this compound acted as an agonist but animal studies have not been reported. 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.[7]

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

  • 2CBCB-NBOMe (NBOMe-TCB-2)
  • 2CBFly-NBOMe (NBOMe-2CB-Fly)
  • 25B-NBOMe (NBOMe-2CB)
  • 25I-NBMD (NBMD-2CI)
  • 25I-NBOH (NBOH-2CI)
  • 25I-NBF (NBF-2CI)

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. ^ Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M. et al. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging 38 (4): 681–693. doi:10.1007/s00259-010-1686-8. ISBN 0025901016868. PMID 21174090.  edit
  4. ^ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor". Journal of Computer-aided Molecular Design 25 (1): 51–66. doi:10.1007/s10822-010-9400-2. PMID 21088982. 
  5. ^ Nichols DE, Frescas SP, Chemel BR, Rehder KS, Zhong D, Lewin AH (June 2008). "High Specific Activity Tritium-Labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): A High Affinity 5-HT2A Receptor-Selective Agonist Radioligand". Bioorganic & Medicinal Chemistry 16 (11): 6116–23. doi:10.1016/j.bmc.2008.04.050. PMC 2719953. PMID 18468904. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2719953. 
  6. ^ Ettrup, A.; Palner, M.; Gillings, N.; Santini, M. A.; Hansen, M.; Kornum, B. R.; Rasmussen, L. K.; Nagren, K. et al. (2010). "Radiosynthesis and Evaluation of 11C-CIMBI-5 as a 5-HT2A Receptor Agonist Radioligand for PET". Journal of Nuclear Medicine 51 (11): 1763. doi:10.2967/jnumed.109.074021. PMID 20956470.  edit
  7. ^ Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE (2006). "Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists". Molecular pharmacology 70 (6): 1956–64. doi:10.1124/mol.106.028720. PMID 17000863. 
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