2CB-Ind
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • (5-bromo-4,7-dimethoxy-2,3-dihydro-1H-inden-1-yl)methanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H16BrNO2
Molar mass286.169 g·mol−1
3D model (JSmol)
  • COc1c(Br)cc(OC)c2c1CCC2CN
  • InChI=1S/C12H16BrNO2/c1-15-10-5-9(13)12(16-2)8-4-3-7(6-14)11(8)10/h5,7H,3-4,6,14H2,1-2H3 checkY
  • Key:HCLPGYNQMVSQIM-UHFFFAOYSA-N checkY
 ☒NcheckY (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]

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[3]
    • N-(2C-B-FLY) fentanyl[4]

Other:

See also

References

  1. ↑ McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE (September 2006). "1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists". Journal of Medicinal Chemistry. 49 (19): 5794–803. CiteSeerX 10.1.1.688.9849. doi:10.1021/jm060656o. PMID 16970404.
  2. ↑ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University. ProQuest 304838368.
  3. ↑ "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.
  4. ↑ "Explore N-(2C-FLY)-Fentanyl | PiHKAL · info". isomerdesign.com.
  5. ↑ 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.
  6. ↑ Beta-hydroxyphenylalkylamines and their use for treating glaucoma
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