2CBFly-NBOMe

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
Identifiers
CAS Number	1335331-42-4 [chemspider];
3D model (JSmol)	Interactive image; Interactive image;
Abbreviations	2CBFly-NBOMe
ChemSpider	26234936 ;
PubChem CID	57469208;
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	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 5HT_2A serotonin receptor subtype.[4][5][6]

Analogues and derivatives

Analogues and derivatives of 2C-B:

25-NB:

25B-NB3OMe
25B-NB4OMe
25B-NBF
25B-NBMD
25B-NBOH
25B-NBOMe (NBOMe-2CB)

Substituted benzofurans:

2C-B-FLY
2CBFly-NBOMe (NBOMe-2CB-Fly)

Other:

2C-B-AN
2C-B-BUTTERFLY
2C-B-DragonFLY
2CB-5-hemifly
2CB-Ind
βk-2C-B (beta-keto 2C-B)
TCB-2 (2C-BCB)

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.[7]

United States

2CBFly-NBOMe is a controlled substance in Vermont as of January 2016.[8]

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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 (1 Suppl): R21–R40. doi:10.1007/s00210-002-0604-4.
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. ProQuest 304838368.
Silva ME; et al. (January 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. CiteSeerX 10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982. Archived from the original on 2014-02-17. Retrieved 2018-07-24.
Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J.; et al. (2010). "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.
Hansen, Martin (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.
"The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
"Regulated Drugs Rule" (PDF). Vermont Department of Health. Retrieved 14 October 2015.

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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 (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. ProQuest 304838368.

[pmid21088982-4] Silva ME; et al. (January 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. CiteSeerX 10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982. Archived from the original on 2014-02-17. Retrieved 2018-07-24.

[5] Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J.; et al. (2010). "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.

[6] Hansen, Martin (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] "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.

[8] "Regulated Drugs Rule" (PDF). Vermont Department of Health. Retrieved 14 October 2015.