2CBFly-NBOMe

2CBFly-NBOMe (NBOMe-2C-B-FLY, Cimbi-31) is a drug of the phenethylamine, DOx, and FLY families. It was 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]

2CBFly-NBOMe

Kekulé, skeletal formula of 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 Y[chemspider]
3D model (JSmol)	Interactive image Interactive image
Abbreviations	2CBFly-NBOMe
ChemSpider	26234936 Y
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 Y Key: CUFCITSPWAZWHS-UHFFFAOYSA-N Y
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). N verify (what is YN ?) Infobox references

Analogues and derivatives

Analogues and derivatives of 2C-B:

25-N:

• 25B-N1POMe
• 25B-NAcPip

25-NB:

• 25B-N(BOMe)2
• 25B-NB
• 25B-NB23DM
• 25B-NB25DM
• 25B-NB3OMe
• 25B-NB4OMe
• 25B-NBF
• 25B-NBMD
• 25B-NBOH
• 25B-NBOMe (NBOMe-2CB)
• 2C-B-DRAGONFLY-NBOH
• 2CBCB-NBOMe
  • DMBMPP
• 2CBFly-NBOMe (NBOMe-2CB-Fly)

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
• 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]