2CBFly-NBOMe

2CBFly-NBOMe
Kekulé, skeletal formula of 2CBFly-NBOMe
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
CAS Number
3D model (JSmol)
Abbreviations 2CBFly-NBOMe
ChemSpider
PubChem CID
InChI
  • 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 checkY
    Key: CUFCITSPWAZWHS-UHFFFAOYSA-N checkY
SMILES
  • COc1ccccc1CNCCc1c2CCOc2c(Br)c2CCOc12
  • COC1=C(CNCCC2=C3OCCC3=C(Br)C3=C2CCO3)C=CC=C1
Properties
Chemical formula
 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

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-N:

  • 25B-N1POMe
  • 25B-NAcPip

25-NB:

25-NM:

  • 25B-NMe7BF
  • 25B-NMe7BT
  • 25B-NMe7Bim
  • 25B-NMe7Box
  • 25B-NMe7DHBF
  • 25B-NMe7Ind
  • 25B-NMe7Indz
  • 25B-NMePyr

Substituted benzofurans:

N-(2C)-fentanyl:

  • N-(2C-B) fentanyl[7]
    • N-(2C-B-FLY) fentanyl[8]

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.[11]

United States

2CBFly-NBOMe is a controlled substance in Vermont as of January 2016.[12]

References

  1. ↑ 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.
  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. ↑ 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.
  5. ↑ 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.
  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. ↑ "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.
  8. ↑ "Explore N-(2C-FLY)-Fentanyl | PiHKAL · info". isomerdesign.com.
  9. ↑ Glennon, Richard A.; Bondarev, Mikhail L.; Khorana, Nantaka; Young, Richard; May, Jesse A.; Hellberg, Mark R.; McLaughlin, Marsha A.; Sharif, Najam A. (November 2004). "β-Oxygenated Analogues of the 5-HT2ASerotonin Receptor Agonist 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–6041. doi:10.1021/jm040082s. ISSN 0022-2623. PMID 15537358.
  10. ↑ Beta-hydroxyphenylalkylamines and their use for treating glaucoma
  11. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
  12. ↑ "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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