25I-NBMD

25I-NBMD
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
IUPAC name
  • N-[(2H-1,3-benzodioxol-4-yl)methyl]-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H20INO4
Molar mass441.265 g·mol−1
3D model (JSmol)
SMILES
  • c13OCOc3cccc1CNCCc(c(OC)cc2I)cc2OC
InChI
  • InChI=1S/C18H20INO4/c1-21-16-9-14(19)17(22-2)8-12(16)6-7-20-10-13-4-3-5-15-18(13)24-11-23-15/h3-5,8-9,20H,6-7,10-11H2,1-2H3 checkY
  • Key:NJNMIPDEUMTYNV-UHFFFAOYSA-N checkY
 ☒NcheckY (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 0.049 nM 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

Analogues and derivatives of 2C-I:

25I-NB*:

References

  1. ↑ Braden MR, Parrish JC, Naylor JC, Nichols DE (December 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. S2CID 15840304.
  2. ↑ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.
  3. ↑ Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, et al. (April 2011). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–93. doi:10.1007/s00259-010-1686-8. PMID 21174090. S2CID 12467684.
  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. ↑ "Archived copy" (PDF). Archived from the original (PDF) on 2015-03-16. Retrieved 2017-04-21.{{cite web}}: CS1 maint: archived copy as title (link)
  6. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
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