Chemistry:2CBFly-NBOMe

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2CBFly-NBOMe
Kekulé, skeletal formula of 2CBFly-NBOMe
2CBFly-NBOMe-3D-balls.png
Names
Preferred IUPAC name
2-(8-Bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b′]difuran-4-yl)-N-[(2-methoxyphenyl)methyl]ethan-1-amine
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).
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Infobox references
Tracking categories (test):

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 5-HT2A 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. ↑ "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. 2002. doi:10.1007/s00210-002-0604-4. 
  2. ↑ 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.
  3. ↑ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University. ProQuest 304838368.
  4. ↑ "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design 25 (1): 51–66. January 2011. doi:10.1007/s10822-010-9400-2. PMID 21088982. Bibcode: 2011JCAMD..25...51S. 
  5. ↑ "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. April 2011. doi:10.1007/s00259-010-1686-8. PMID 21174090. 
  6. ↑ 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.
  7. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014" (in en). http://www.legislation.gov.uk/uksi/2014/1106/made. 
  8. ↑ "Regulated Drugs Rule". Vermont Department of Health. http://healthvermont.gov/regs/documents/regulated_drugs_rule_20160101.pdf. 



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