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2CB-ind structure.png
Systematic (IUPAC) name
Clinical data
Routes of
Legal status
Legal status
  • Uncontrolled
CAS Number 912342-23-5 N
ATC code none
PubChem CID 16086368
ChemSpider 17245022 YesY
Chemical data
Formula C12H16BrNO2
Molar mass 286.164 g/mol
 NYesY (what is this?)  (verify)

2CB-Ind is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, discovered in 1974 by Alexander Shulgin. It acts as a moderately potent and selective agonist for the 5-HT2A and 5-HT2C receptors, but unlike the corresponding benzocyclobutene derivative TCB-2 which is considerably more potent than the parent compound 2C-B, 2CB-Ind is several times weaker, with racemic 2CB-Ind having a Ki of 47nM at the human 5-HT2A receptor, only slightly more potent than the mescaline analogue (R)-jimscaline.[1][2]

See also[edit]


  1. ^ McLean, TH; et al. (2006). "1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists". Journal of Medicinal Chemistry. 49 (19): 5794–803. doi:10.1021/jm060656o. PMID 16970404. 
  2. ^ Braden, Michael Robert (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University.