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
Abbreviations
2CBFly-NBOMe
ChemSpider
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
Y Key: CUFCITSPWAZWHS-UHFFFAOYSA-N
Y
COc1ccccc1CNCCc1c2CCOc2c(Br)c2CCOc12
COC1=C(CNCCC2=C3OCCC3=C(Br)C3=C2CCO3)C=CC=C1
Properties
C 20 H 22 Br N O 3
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).
Chemical compound
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]
^ 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 .
^ 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.
^ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University. ProQuest 304838368 .
^ 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 .
^ 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 .
^ 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 .