2CBFly-NBOMe

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
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). verify (what is ?) 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 5-HT_2A serotonin receptor subtype.^[4]^[5]^[6]

Analogues and derivatives

Analogues and derivatives of 2C-B:

25-N:

25-NB:

25-NM:

Substituted benzofurans:

2C-B-FLY
- 2C-B-BUTTERFLY
- 2C-B-DRAGONFLY
2CBFly-NBOMe (NBOMe-2CB-Fly)
DOB-FLY
DOB-2-DRAGONFLY-5-BUTTERFLY

N-(2C)-fentanyl:

N-(2C-B) fentanyl^[7]
- N-(2C-B-FLY) fentanyl^[8]

Other:

BOB
BOH-2C-B, β-Hydroxy-2C-B, βOH-2CB^[9]^[10]
BMB
2C-B-5-hemifly
2C-B-aminorex (2C-B-AR)
2C-B-AN
2C-B-BZP
2C-B-FLY-NB2EtO5Cl
2C-B-PP
2CB-Ind
βk-2C-B (beta-keto 2C-B)
N-Ethyl-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.^[11]

United States

2CBFly-NBOMe is a controlled substance in Vermont as of January 2016.^[12]

References

^ 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.
^ "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.
^ "Explore N-(2C-FLY)-Fentanyl | PiHKAL · info". isomerdesign.com.
^ 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.
^ Beta-hydroxyphenylalkylamines and their use for treating glaucoma
^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
^ "Regulated Drugs Rule" (PDF). Vermont Department of Health. Archived from the original (PDF) on 5 June 2016. Retrieved 14 October 2015.

[1] 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.

[2] 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.

[3] Braden MR (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University. ProQuest 304838368.

[pmid21088982-4] 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.

[5] 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.

[6] 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.

[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. Archived from the original (PDF) on 5 June 2016. Retrieved 14 October 2015.

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