TCB-2

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TCB-2
TCB-2.png
Systematic (IUPAC) name
[(7R)-3-Bromo-2,5-dimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl]methanamine
Clinical data
Routes of
administration
Oral
Legal status
Legal status
  • Uncontrolled
Identifiers
CAS Number 912440-88-1 YesY
912342-36-0 (hydrobromide)
ATC code none
PubChem CID 16086382
ChemSpider 17245036
ChEMBL CHEMBL379637
Chemical data
Formula C11H14BrNO2
Molar mass 272.14 g/mol
  (verify)

TCB-2 is a hallucinogen, discovered in 2006 by Thomas McLean, working in the lab of Prof. 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 0.26nM 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.[2] This high potency and selectivity has made TCB-2 useful for distinguishing 5-HT2A mediated responses from those produced by other similar receptors.[3] 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.[4][5][6][7]

See also[edit]

References[edit]

  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. ^ 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
  3. ^ 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
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ 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 3477617free to read. PMID 22722027.