TCB-2

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TCB-2
TCB-2.png
Clinical data
Routes of
administration
Oral
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C11H14BrNO2
Molar mass 272.14 g·mol−1
3D model (JSmol)
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TCB-2 is a hallucinogen discovered in 2006 by Thomas McLean working in the lab of David Nichols at Purdue University where it was named 2C-BCB.[1] It is a conformationally-restricted derivative of the phenethylamine 2C-B, also a hallucinogen, and acts as a potent agonist for the 5-HT2A and 5-HT2C receptors with a Ki of 0.26 nM at the human 5-HT2A 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.[1] This high potency and selectivity has made TCB-2 useful for distinguishing 5-HT2A mediated responses from those produced by other similar receptors.[2] TCB-2 has similar but not identical effects in animals to related phenethylamine hallucinogens such as DOI, and has been used for studying how the function of the 5-HT2A receptor differs from that of other serotonin receptors in a number of animal models, such as studies of cocaine addiction and neuropathic pain.[3][4][5][6]

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References[edit]

  1. ^ a b McLean, T. H.; Parrish, J. C.; Braden, M. R.; Marona-Lewicka, D; Gallardo-Godoy, A; Nichols, D. E. (2006). "1-Aminomethylbenzocycloalkanes: Conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists". Journal of Medicinal Chemistry. 49 (19): 5794–803. CiteSeerX 10.1.1.688.9849Freely accessible. doi:10.1021/jm060656o. PMID 16970404. 
  2. ^ Chang, C. W.; Poteet, E; Schetz, J. A.; Gümüş, Z. H.; Weinstein, H (2009). "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. 56 Suppl 1: 213–25. doi:10.1016/j.neuropharm.2008.07.049. PMC 2635340Freely accessible. PMID 18762202. 
  3. ^ Fox, M. A.; French, H. T.; Laporte, J. L.; Blackler, A. R.; Murphy, D. L. (2009). "The serotonin 5-HT2A receptor agonist TCB-2: A behavioral and neurophysiological analysis". Psychopharmacology. 212 (1): 13–23. doi:10.1007/s00213-009-1694-1. PMID 19823806. 
  4. ^ Aira, Z.; Buesa, I.; Salgueiro, M.; Bilbao, J.; Aguilera, L.; Zimmermann, M.; Azkue, J. J. (2010). "Subtype-specific changes in 5-HT receptor-mediated modulation of C fibre-evoked spinal field potentials are triggered by peripheral nerve injury". Neuroscience. 168 (3): 831–841. doi:10.1016/j.neuroscience.2010.04.032. PMID 20412834. 
  5. ^ Katsidoni, V.; Apazoglou, K.; Panagis, G. (2010). "Role of serotonin 5-HT2A and 5-HT2C receptors on brain stimulation reward and the reward-facilitating effect of cocaine". Psychopharmacology. 213 (2–3): 337–354. doi:10.1007/s00213-010-1887-7. PMID 20577718. 
  6. ^ Zhang, G.; Ásgeirsdóttir, H. N.; Cohen, S. J.; Munchow, A. H.; Barrera, M. P.; Stackman, R. W. (2012). "Stimulation of serotonin 2A receptors facilitates consolidation and extinction of fear memory in C57BL/6J mice". Neuropharmacology. 64: 403–13. doi:10.1016/j.neuropharm.2012.06.007. PMC 3477617Freely accessible. PMID 22722027.