25I-NBMD

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]

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 Y
  • Key:NJNMIPDEUMTYNV-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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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