25I-NBMD

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25I-NBMD
25I-NBMD.svg
Systematic (IUPAC) name
2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2,3-methylenedioxyphenyl)methyl]ethanamine
Clinical data
Legal status ?
Identifiers
CAS number 919797-25-4 N
ATC code ?
ChemSpider 26234932 YesY
Chemical data
Formula C18H20INO4 
Mol. mass 441.259 g/mol
 N (what is this?)  (verify)

25I-NBMD (NBMD-2C-I, Cimbi-29) is a derivative of the phenethylamine hallucinogen 2C-I, discovered in 2006 by a team at Purdue University led by David Nichols. It acts as a potent partial agonist for the 5HT2A receptor with a Ki of 0.049nM at the human 5HT2A receptor.[1][2][3] The corresponding 4-bromo analogue 25B-NBMD has been used for molecular dynamics studies on the shape of the 5-HT2A receptor.[4] Common doses are reported to be between 500 µg and 1.5 mg. Although the low end of the dose response curve is similar to LSD, being active at 500 µg, some reports show 1.5–2.0 mg being a low dose, making it up to four times less active than its nbome counterpart 25I-NBOMe. As a recreational drug, 25I-NBMD has not been on the open market for long; therefore there are very few reports about its use.

See also[edit]

References[edit]

  1. ^ 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. 
  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.; Madsen, J. (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. PMID 21174090.  edit
  4. ^ Isberg V, Balle T, Sander T, Jørgensen FS, Gloriam DE (February 2011). "G protein- and agonist-bound serotonin 5-HT2A receptor model activated by steered molecular dynamics simulations". Journal of Chemical Information and Modeling 51 (2): 315–25. doi:10.1021/ci100402f. PMID 21261291.