2CBFly-NBOMe: Difference between revisions

2CBFly-NBOMe
Names
	Other names 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
CAS Number	1335331-42-4;
3D model (JSmol)	Interactive image; Interactive image;
Abbreviations	2CBFly-NBOMe
ChemSpider	26234936 ;
CompTox Dashboard (EPA)	DTXSID40726752 ;
	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 Key: CUFCITSPWAZWHS-UHFFFAOYSA-N ;
	SMILES COc1ccccc1CNCCc1c2CCOc2c(Br)c2CCOc12; COC1=C(CNCCC2=C3OCCC3=C(Br)C3=C2CCO3)C=CC=C1;
Properties
Chemical formula	C; 20NH; 22O; 3Br
Molar mass	404.298 g mol-1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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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 E. Nichols.^[3] It acts as a potent partial agonist for the 5HT_2A serotonin receptor subtype.^[4]^[5]^[6]

References

^ Elz S; et al. (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}}: Explicit use of et al. in: |author= (help)
^ Heim, Ralf (2004). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (PhD.). Free University of Berlin.
^ Braden, Michael Robert (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University.
^ Silva ME; et al. (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}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)
^ 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.
^ Hansen, Martin (2011). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (PhD.). University of Copenhagen.

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[1] Elz S; et al. (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}}: Explicit use of et al. in: |author= (help)

[2] Heim, Ralf (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, Michael Robert (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University.

[pmid21088982-4] Silva ME; et al. (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}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)

[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.

[6] Hansen, Martin (2011). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (PhD.). University of Copenhagen.

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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, ''et al.'' |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>{{Cite thesis |type=PhD. |title=Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts |url=http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 |last=Heim |first=Ralf |year=2004 |publisher=Free University of Berlin }}</ref> and subsequently investigated in more detail by a team at [[Purdue University]] led by [[David Nichols]].<ref>{{Cite thesis |type=PhD. |title=Towards a biophysical understanding of hallucinogen action |url=http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 |author= |last=Braden |first=Michael Robert |year=2007 |publisher=Purdue University }}</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, ''et al.'' |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><ref>{{Cite thesis |type=PhD. |title=Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain |url=http://bitnest.ca/external.php?id=%2518%253A3%25172%251BE%2524K%255BG%2521%2524%257D%2504%2504V |last=Hansen |first=Martin |year=2011 |publisher=University of Copenhagen }}</ref>
+'''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, ''et al.'' |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>{{Cite thesis |type=PhD. |title=Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts |url=http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 |last=Heim |first=Ralf |year=2004 |publisher=Free University of Berlin }}</ref> and subsequently investigated in more detail by a team at [[Purdue University]] led by [[David E. Nichols]].<ref>{{Cite thesis |type=PhD. |title=Towards a biophysical understanding of hallucinogen action |url=http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 |author= |last=Braden |first=Michael Robert |year=2007 |publisher=Purdue University }}</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, ''et al.'' |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><ref>{{Cite thesis |type=PhD. |title=Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain |url=http://bitnest.ca/external.php?id=%2518%253A3%25172%251BE%2524K%255BG%2521%2524%257D%2504%2504V |last=Hansen |first=Martin |year=2011 |publisher=University of Copenhagen }}</ref>
 ==See also==