25I-NBMD

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25I-NBMD
25I-NBMD.svg
Legal status
Legal status
Identifiers
CAS Number
  • 919797-25-4 No
PubChem CID
  • 57507899
ChemSpider
  • 26234932 YesY
UNII
  • R99110126K
Chemical and physical data
Formula C18H20INO4
Molar mass 441.259 g/mol
3D model (JSmol)
  • Interactive image
 NoYesY (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]

Legality

Sweden

The Riksdag added 25I-NBMD to Narcotic Drugs Punishments Act under swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of January 16, 2015, published by Medical Products Agency (MPA) in regulation LVFS 2014:11 listed as 25I-NBMD, and 2-(4-jodo-2,5-dimetoxifenyl)-N-[(2,3-metylendioxifenyl)metyl]etanamin.[5]

United Kingdom

This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.[6]


Analogues and derivatives

References

  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.; 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): 681–93. doi:10.1007/s00259-010-1686-8. PMID 21174090. 
  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. 
  5. ^ https://lakemedelsverket.se/upload/lvfs/LVFS_2014_11.pdf
  6. ^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk. 
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