2CBFly-NBOMe

Last updated
2CBFly-NBOMe
2CBFly-NBOMe-2D.svg
2CBFly-NBOMe-3D-balls.png
Clinical data
Other names2C-B-FLY-NBOMe; NBOMe-2C-B-FLY; Cimbi-31; N-(2-Methoxybenzyl)-2C-B-FLY
Drug class Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 2-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b′]difuran-4-yl)-N-[(2-methoxyphenyl)methyl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H22BrNO3
Molar mass 404.304 g·mol−1
3D model (JSmol)
  • COc1ccccc1CNCCc1c2CCOc2c(Br)c2CCOc12
  • InChI=1S/C20H22BrNO3/c1-23-17-5-3-2-4-13(17)12-22-9-6-14-15-7-10-25-20(15)18(21)16-8-11-24-19(14)16/h2-5,22H,6-12H2,1H3 Yes check.svgY
  • Key:CUFCITSPWAZWHS-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

2CBFly-NBOMe, also known as NBOMe-2C-B-FLY or as Cimbi-31, is a serotonin receptor modulator of the phenethylamine, DOx, and FLY families. It was indirectly derived from the phenethylamine hallucinogen 2C-B is and related to benzodifurans like 2C-B-FLY and N-benzylphenethylamines like 25B-NBOMe.

Contents

Interactions

Pharmacology

Pharmacodynamics

2CBFly-NBOMe acts as a potent partial agonist for the 5-HT2A serotonin receptor subtype. [1] [2] [3]

History

2CBFly-NBOMe was discovered in 2002, [4] and further researched by Ralf Heim at the Free University of Berlin, [5] and subsequently investigated in more detail by a team at Purdue University led by David E. Nichols. [6]

Society and culture

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]

See also

References

  1. ↑ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. Bibcode:2011JCAMD..25...51S. CiteSeerX   10.1.1.688.2670 . doi:10.1007/s10822-010-9400-2. PMID   21088982. S2CID   3103050.
  2. ↑ 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.
  3. ↑ Hansen M (2011). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (PhD.). University of Copenhagen. Archived from the original on 2013-10-22. Retrieved 2012-11-02.
  4. ↑ Elz S, Klass T, Heim R, Warnke U, Pertz HH (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.
  5. ↑ Heim R (2004). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (PhD.). Free University of Berlin.
  6. ↑ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University. ProQuest   304838368.
  7. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
  8. ↑ "Regulated Drugs Rule" (PDF). Vermont Department of Health. Archived from the original (PDF) on 5 June 2016. Retrieved 14 October 2015.
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