2CBFly-NBOMe

2CBFly-NBOMe
Names
Other names
N-(2-Methoxybenzyl)-1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b’]difuran-4-yl)-2-aminoethane
Identifiers
3D model (JSmol)
Abbreviations 2CBFly-NBOMe
ChemSpider
Properties
C20H22BrNO3
Molar mass 404.298 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

2CBFly-NBOMe (NBOMe-2C-B-FLY, Cimbi-31) is a compound indirectly derived from the phenethylamine hallucinogen 2C-B, and related to benzodifurans like 2C-B-FLY and N-benzylphenethylamines like 25I-NBOMe. It was discovered in 2002,[1] and further researched by Ralf Heim at the Free University of Berlin,[2] and subsequently investigated in more detail by a team at Purdue University led by David E. Nichols.[3] It acts as a potent partial agonist for the 5HT2A serotonin receptor subtype.[4][5][6]

Analogues and derivatives

Analogues and derivatives of 2C-B:

25-NB:

Substituted benzofurans:

Other:

Legality

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.[7]

United States

2CBFly-NBOMe is a controlled substance in Vermont as of January 2016.[8]

References

  1. Elz S; et al. (2002). "Development of highly potent partial agonists and chiral antagonists as tools for the study of 5-HT2A-receptor mediated function". Naunyn-Schmiedeberg's Archives of Pharmacology. 365 (1 Suppl): R21–R40. doi:10.1007/s00210-002-0604-4.
  2. Heim, Ralf (2004). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (PhD.). Free University of Berlin.
  3. Braden, Michael Robert (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University.
  4. Silva ME; et al. (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor" (Submitted manuscript). Journal of Computer-aided Molecular Design. 25 (1): 51–66. doi:10.1007/s10822-010-9400-2. PMID 21088982.
  5. 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.
  6. Hansen, Martin (2011). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (PhD.). University of Copenhagen.
  7. "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
  8. "Regulated Drugs Rule" (PDF). Vermont Department of Health. Retrieved 14 October 2015.


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