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'''2CBFly-NBOMe''' ('''NBOMe-2C-B-FLY''', '''Cimbi-31''') is a compound indirectly derived from the [[phenethylamine]] [[psychedelic|hallucinogen]] [[2C-B]], and related to benzodifurans like [[2C-B-FLY]] and ''N''-benzylphenethylamines like [[NBOMe-2C-I]]. It was discovered in 2002,<ref>{{cite journal | author = Elz S, Kläß T, Heim R, Warnke U, Pertz HH | title = Development of highly potent partial agonists and chiral antagonists as tools for the study of 5-HT2A-receptor mediated function | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | yer = 2002 | volume = 365 | pages = R29}}</ref> and further researched by Ralf Heim at the [[Free University of Berlin]],<ref>[http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)]</ref> and subsequently investigated in more detail by a team at [[Purdue University]] led by [[David Nichols]].<ref>[http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.]</ref> It acts as a potent [[partial agonist]] for the [[5HT2A receptor|5HT<sub>2A</sub>]] [[serotonin]] [[Receptor (biochemistry)|receptor]] subtype,<ref name="pmid21088982">{{cite journal |author=Silva ME, Heim R, Strasser A, Elz S, Dove S |title=Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor |journal=Journal of Computer-aided Molecular Design |volume=25 |issue=1 |pages=51–66 |year=2011 |month=January |pmid=21088982 |doi=10.1007/s10822-010-9400-2 |url=}}</ref><ref>{{Cite doi|10.1007/s00259-010-1686-8}}</ref> with a [[Dissociation constant|Ki]] of 0.14nM at the rat 5HT<sub>2A</sub> receptor.
'''2CBFly-NBOMe''' ('''NBOMe-2C-B-FLY''', '''Cimbi-31''') is a compound indirectly derived from the [[phenethylamine]] [[psychedelic|hallucinogen]] [[2C-B]], and related to benzodifurans like [[2C-B-FLY]] and ''N''-benzylphenethylamines like [[NBOMe-2C-I]]. It was discovered in 2002,<ref>{{cite journal | author = Elz S, Kläß T, Heim R, Warnke U, Pertz HH | title = Development of highly potent partial agonists and chiral antagonists as tools for the study of 5-HT2A-receptor mediated function | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 365 | pages = R29 | year = 2002}}</ref> and further researched by Ralf Heim at the [[Free University of Berlin]],<ref>[http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)]</ref> and subsequently investigated in more detail by a team at [[Purdue University]] led by [[David Nichols]].<ref>[http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.]</ref> It acts as a potent [[partial agonist]] for the [[5HT2A receptor|5HT<sub>2A</sub>]] [[serotonin]] [[Receptor (biochemistry)|receptor]] subtype,<ref name="pmid21088982">{{cite journal |author=Silva ME, Heim R, Strasser A, Elz S, Dove S |title=Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor |journal=Journal of Computer-aided Molecular Design |volume=25 |issue=1 |pages=51–66 |year=2011 |month=January |pmid=21088982 |doi=10.1007/s10822-010-9400-2 |url=}}</ref><ref>{{Cite doi|10.1007/s00259-010-1686-8}}</ref> with a [[Dissociation constant|Ki]] of 0.14nM at the rat 5HT<sub>2A</sub> receptor.


==See also==
==See also==

Revision as of 11:49, 5 June 2011

2CBFly-NBOMe
Kekulé, skeletal formula of 2CBFly-NBOMe
Names
IUPAC name
N-(2-Methoxybenzyl)-1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b’]difuran-4-yl)-2-aminoethane[citation needed]
Identifiers
3D model (JSmol)
Abbreviations 2CBFly-NBOMe
  • 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
    Key: CUFCITSPWAZWHS-UHFFFAOYSA-N
  • COc1ccccc1CNCCc1c2CCOc2c(Br)c2CCOc12
  • COC1=C(CNCCC2=C3OCCC3=C(Br)C3=C2CCO3)C=CC=C1
Properties
C=20
Molar mass 164.084 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 NBOMe-2C-I. 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 Nichols.[3] It acts as a potent partial agonist for the 5HT2A serotonin receptor subtype,[4][5] with a Ki of 0.14nM at the rat 5HT2A receptor.

See also

References

  1. ^ Elz S, Kläß 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: R29.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^ Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)
  3. ^ Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.
  4. ^ Silva ME, Heim R, Strasser A, Elz S, Dove S (2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor". Journal of Computer-aided Molecular Design. 25 (1): 51–66. doi:10.1007/s10822-010-9400-2. PMID 21088982. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  5. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1007/s00259-010-1686-8, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1007/s00259-010-1686-8 instead.