2CBCB-NBOMe

2CBCB-NBOMe (NBOMe-TCB-2) is a compound indirectly derived from the phenethylamine series of hallucinogens, which was discovered in 2007 at Purdue University as part of the ongoing research program of the team led by David Nichols focusing on the mapping of the specific amino acid residues responsible for ligand binding to the 5HT_2A receptor. 2CBCB-NBOMe acts as a potent and selective agonist for the 5-HT_2A and 5-HT_2C receptors, with a Ki of 0.27 nM at the human 5-HT_2A receptor, a similar potency to other agonists such as TCB-2, NBOMe-2C-I and Bromo-DragonFLY.^[1]

2CBCB-NBOMe

Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Class A
Identifiers
IUPAC name N-[(3-bromo-2,5-dimethoxy-bicyclo[4,2,0]octa-1,3,5-trien-7-yl)methyl]-1-(2-methoxyphenyl)methanamine
CAS Number	1354634-09-5 N
PubChem CID	57483909
ChemSpider	26234935 Y
UNII	WGI3S41A26
CompTox Dashboard (EPA)	DTXSID501028189
Chemical and physical data
Formula	C19H22BrNO3
Molar mass	392.293 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1ccccc1CNCC3c2c(C3)c(OC)c(Br)cc2OC
InChI InChI=1S/C19H22BrNO3/c1-22-16-7-5-4-6-12(16)10-21-11-13-8-14-18(13)17(23-2)9-15(20)19(14)24-3/h4-7,9,13,21H,8,10-11H2,1-3H3/t13-/m0/s1 Y Key:CLSBQRBXTFTLEX-ZDUSSCGKSA-N Y
NY (what is this?)  (verify)

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^[2]
  • N-(2C-B-FLY) fentanyl^[3]

Other:

• BOB
• BOH-2C-B, β-Hydroxy-2C-B, βOH-2CB^[4][5]
• 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.^[6]

United States

2CBCB-NBOMe is a controlled substance in Vermont as of January 2016.^[7]