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2CBFly-NBOMe

Names
Preferred IUPAC name 2-(8-Bromo-2,3,6,7-tetrahydrobenzodifuran-4-yl)-N-ethan-1-amine
Identifiers
CAS Number	1335331-42-4
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,6-12H2,1H3Key: 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 , 100 kPa). N 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, and further researched by Ralf Heim at the Free University of Berlin, and subsequently investigated in more detail by a team at Purdue University led by David E. Nichols. It acts as a potent partial agonist for the 5-HT_2A serotonin receptor subtype.

Analogues and derivatives

Analogues and derivatives of 2C-B:

25-N:

• 25B-N1POMe
• 25B-NAcPip

25-NB:

• 25B-NB
• 25B-NB23DM
• 25B-NB25DM
• 25B-NB3OMe
• 25B-NB4OMe
• 25B-NBF
• 25B-NBMD
• 25B-NBOH
• 25B-NBOMe (NBOMe-2CB)
  • DMBMPP

25-NM:

• 25B-NMe7BF
• 25B-NMe7BT
• 25B-NMe7Bim
• 25B-NMe7Box
• 25B-NMe7DHBF
• 25B-NMe7Ind
• 25B-NMe7Indz
• 25B-NMePyr

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
  • N-(2C-B-FLY) fentanyl

Other:

• BOB
• BOH-2C-B, β-Hydroxy-2C-B, βOH-2CB
• 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.

United States

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

References

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.
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.

• 25-NB (psychedelics)
• Bromobenzene derivatives
• Phenethylamines
• Psychedelic phenethylamines
• Serotonin receptor agonists
• Heterocyclic compounds with 3 rings
• Dihydrofurans
• Secondary amines
• 2-Methoxyphenyl compounds