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'''2CBFly-NBOMe''' ('''NBOMe-2C-B-FLY''', '''Cimbi-31''') is a compound indirectly derived from the [[phenethylamine]] [[Psychedelic drug|hallucinogen]] [[2C-B]], and related to benzodifurans like [[2C-B-FLY]] and ''N''-benzylphenethylamines like [[25I-NBOMe]]. It was discovered in 2002,<ref>{{cite journal |author= Elz S |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 |issue= 1 Suppl|pages= R29 |year= 2002|doi=10.1007/s00210-002-0604-4|display-authors=etal}}</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 |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 |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 |date=January 2011 |pmid=21088982 |doi=10.1007/s10822-010-9400-2 |url=|display-authors=etal}}</ref><ref>{{Cite journal |doi= 10.1007/s00259-010-1686-8 |last= Ettrup |first= A. | last2= Hansen | first2= M. |last3= Santini | first3= M. A. |last4= Paine | first4= J. |last5= Gillings | first5= N. |last6= Palner | first6= M. |last7= Lehel | first7= S. |last8= Herth | first8= M. M. |last9= Madsen | first9= J. | first10= J. | last10= Kristensen |displayauthors=9 | first11= M. | last11 = Begtrup | first12= G. M. | last12 = Knudsen | title = Radiosynthesis and ''in vivo'' evaluation of a series of substituted <sup>11</sup>C-phenethylamines as 5-HT<sub>2A</sub> agonist PET tracers |journal= European Journal of Nuclear Medicine and Molecular Imaging |volume= 38 |issue= 4 |pages= 681–93 |year= 2010 |pmid= 21174090 }}
'''2CBFly-NBOMe''' ('''NBOMe-2C-B-FLY''', '''Cimbi-31''') is a compound indirectly derived from the [[phenethylamine]] [[Psychedelic drug|hallucinogen]] [[2C-B]], and related to benzodifurans like [[2C-B-FLY]] and ''N''-benzylphenethylamines like [[25I-NBOMe]]. It was discovered in 2002,<ref>{{cite journal |author= Elz S |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 |issue= 1 Suppl|pages= R21–R40 |year= 2002|doi=10.1007/s00210-002-0604-4|display-authors=etal}}</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 |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 |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 |date=January 2011 |pmid=21088982 |doi=10.1007/s10822-010-9400-2 |url=http://bitnest.ca/external.php?id%3D%7DbxUgX%5DCY%04%04%7Cx%7D%19%05V%5BL%0BPIw%60b|display-authors=etal|format=Submitted manuscript }}</ref><ref>{{Cite journal |doi= 10.1007/s00259-010-1686-8 |last= Ettrup |first= A. | last2= Hansen | first2= M. |last3= Santini | first3= M. A. |last4= Paine | first4= J. |last5= Gillings | first5= N. |last6= Palner | first6= M. |last7= Lehel | first7= S. |last8= Herth | first8= M. M. |last9= Madsen | first9= J. | first10= J. | last10= Kristensen |displayauthors=9 | first11= M. | last11 = Begtrup | first12= G. M. | last12 = Knudsen | title = Radiosynthesis and ''in vivo'' evaluation of a series of substituted <sup>11</sup>C-phenethylamines as 5-HT<sub>2A</sub> agonist PET tracers |journal= European Journal of Nuclear Medicine and Molecular Imaging |volume= 38 |issue= 4 |pages= 681–93 |year= 2010 |pmid= 21174090 }}
</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>
</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>


Revision as of 16:51, 24 July 2018

2CBFly-NBOMe
Kekulé, skeletal formula of 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
3D model (JSmol)
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 checkY
    Key: CUFCITSPWAZWHS-UHFFFAOYSA-N checkY
  • COc1ccccc1CNCCc1c2CCOc2c(Br)c2CCOc12
  • COC1=C(CNCCC2=C3OCCC3=C(Br)C3=C2CCO3)C=CC=C1
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).
☒N verify (what is checkY☒N ?)

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 5HT2A serotonin receptor subtype.[4][5][6]

Analogues and derivatives

Analogues and derivatives of 2C-B:

25-N:

25-NB:

25-NM:

Substituted benzofurans:

N-(2C)-fentanyl:

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; 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 (1 Suppl): R21 – R40. doi:10.1007/s00210-002-0604-4.
  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.
  4. ^ Silva ME; et al. (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor" (Submitted manuscript). Journal of Computer-aided Molecular Design. 25 (1): 51–66. doi:10.1007/s10822-010-9400-2. PMID 21088982.
  5. ^ Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J.; Kristensen, J.; Begtrup, M.; Knudsen, G. M. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–93. doi:10.1007/s00259-010-1686-8. PMID 21174090. {{cite journal}}: Unknown parameter |displayauthors= ignored (|display-authors= suggested) (help)
  6. ^ Hansen, Martin (2011). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (PhD.). University of Copenhagen.
  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. Retrieved 14 October 2015.


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