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 5HT2A receptor. 2CBCB-NBOMe acts as a potent and selective agonist for the 5-HT2A and 5-HT2C receptors, with a Ki of 0.27 nM at the human 5-HT2A 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
  • N-[(3-bromo-2,5-dimethoxy-bicyclo[4,2,0]octa-1,3,5-trien-7-yl)methyl]-1-(2-methoxyphenyl)methanamine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC19H22BrNO3
Molar mass392.293 g·mol−1
3D model (JSmol)
  • COc1ccccc1CNCC3c2c(C3)c(OC)c(Br)cc2OC
  • 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 checkY
  • Key:CLSBQRBXTFTLEX-ZDUSSCGKSA-N checkY
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Analogues and derivatives

Analogues and derivatives of 2C-B:

25-N:

  • 25B-N1POMe
  • 25B-NAcPip

25-NB:

25-NM:

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

Substituted benzofurans:

N-(2C)-fentanyl:

  • N-(2C-B) fentanyl[2]
    • N-(2C-B-FLY) fentanyl[3]

Other:

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]

References
  1. Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D.). Purdue University. ProQuest 304838368.
  2. "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.
  3. "Explore N-(2C-FLY)-Fentanyl | PiHKAL · info". isomerdesign.com.
  4. 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.
  5. Beta-hydroxyphenylalkylamines and their use for treating glaucoma
  6. "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
  7. "Regulated Drugs Rule" (PDF). Vermont Department of Health. Retrieved 14 October 2015.
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