TCB-2

TCB-2
Systematic (IUPAC) name
	1-[(7R)-3-bromo-2,5-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methanamine
Clinical data
Pregnancy cat.	?
Legal status	Uncontrolled
Routes	Oral
Identifiers
CAS number	912440-88-1 ; 912342-36-0 (hydrobromide)
ATC code	None
PubChem	CID 16086382
Chemical data
Formula	C11H14BrNO2
Mol. mass	272.14 g/mol
	SMILES COc1c(Br)cc(OC)c2c1CC2CN;
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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-HT_2A and 5-HT_2C receptors with a K_i of 0.26nM at the human 5-HT_2A 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-HT_2A 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 5HT2A 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]

The related benzocyclobutene analogs of mescaline, Tomscaline and Bromotomscaline also exhibit significantly higher potency than their parent compound. The N-BnOMe (N-ortho-methoxybenzyl) analogs of TCB-2, Tomscaline, and Bromotomscaline were also synthesized.

[edit] See also

[edit] References

^ 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.
^ 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
^ 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
^ 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. edit
^ 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. edit
^ 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. edit
^ 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. doi:10.1016/j.neuropharm.2012.06.007. PMID 22722027. edit

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[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. edit

[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. edit

[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. edit

[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. doi:10.1016/j.neuropharm.2012.06.007. PMID 22722027. edit

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TCB-2

[edit] See also

[edit] References

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