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TCB-2
Systematic (IUPAC) name
1-[(7R)-3-bromo-2,5-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methanamine
Identifiers
CAS number 912440-88-1
912342-36-0 (hydrobromide)
ATC code  ?
PubChem 16086382
Chemical data
Formula C 11H14BrNO2  
Mol. mass 272.14 g/mol
SMILES eMolecules & PubChem
Synonyms TCB-2, ((8R)-4-bromo-2,5-dimethoxy-8-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methanamine
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

2C-BCB, also known as TCB-2 , is a conformationally restricted derivative of the phenethylamine derived hallucinogen 2C-B, discovered in 2006 by a team at Purdue University where it has been named 2C-BCB.[1] The compound has been made commercially available under the name TCB-2.[2] It acts as a potent agonist for the 5HT2A and 5HT2C receptors with a Ki of 0.26nM at the human 5HT2A receptor. In drug-substitution experiments in rats, TCB-2 was found to be of similar potency to both LSD and Br-DFLY, ranking it among the most potent phenethylamine hallucinogens yet discovered.[3] This high potency and selectivity has made TCB-2 useful for distinguishing 5-HT2A mediated responses from those produced by other similar receptors.[4]

References

  1. ^ Yu B, Becnel J, Zerfaoui M, Rohatgi R, Boulares AH, Nichols CD (November 2008). "Serotonin 5-hydroxytryptamine(2A) receptor activation suppresses tumor necrosis factor-alpha-induced inflammation with extraordinary potency". J. Pharmacol. Exp. Ther. 327 (2): 316–23. doi:10.1124/jpet.108.143461. PMID 18708586.  
  2. ^ Tocris
  3. ^ McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE. 1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists. Journal of Medicinal Chemistry. 2006 Sep 21;49(19):5794-803. PMID 16970404
  4. ^ Chang CW, Poteet E, Schetz JA, Gümüş ZH, Weinstein H. Towards a quantitative representation of the cell signaling mechanisms of hallucinogens: measurement and mathematical modeling of 5-HT1A and 5-HT2A receptor-mediated ERK1/2 activation. Neuropharmacology. 2009;56 Suppl 1:213-25. PMID 18762202
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