View source for TCB-2

{{Drugbox
| IUPAC_name                = 1-[(7''R'')-3-bromo-2,5-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methanamine
| image                    = TCB-2.png
| CAS_number               = 912440-88-1
| CAS_supplemental         = <br />912342-36-0 ([[hydrobromide]])
| ATC_prefix               = none
| ATC_suffix               = 
| PubChem                  = 16086382
| DrugBank                 = 
| C = 11 | H = 14 | Br = 1 | N = 1 | O = 2
| molecular_weight         = 272.14 g/mol
| smiles                   = COc1c(Br)cc(OC)c2c1CC2CN
| bioavailability          = 
| metabolism               = 
| elimination_half-life    = 
| excretion                = 
| pregnancy_category       = 
| legal_status             = Uncontrolled
| routes_of_administration = Oral
}}

'''2C-BCB''', also known as '''TCB-2''' , is a [[conformation|conformationally]]-restricted [[chemical derivative|derivative]] of the [[substituted phenethylamine|phenethylamine]] [[hallucinogen]] [[2C-B]], discovered in 2006 by a team at [[Purdue University]] where it has been named ''2C-BCB''.<ref>{{cite journal | author = Yu B, Becnel J, Zerfaoui M, Rohatgi R, Boulares AH, Nichols CD | title = Serotonin 5-hydroxytryptamine(2A) receptor activation suppresses tumor necrosis factor-alpha-induced inflammation with extraordinary potency | journal = J. Pharmacol. Exp. Ther. | volume = 327 | issue = 2 | pages = 316–23 | year = 2008 | month = November | pmid = 18708586 | doi = 10.1124/jpet.108.143461 | url = }}</ref> The compound has been made commercially-available under the name ''TCB-2''.<ref>[http://www.tocris.com/dispprod.php?ItemId=166910 Tocris]</ref> It acts as a [[potency (pharmacology)|potent]] [[agonist]] for the [[5-HT2A receptor|5-HT<sub>2A</sub>]] and [[5-HT2C receptor|5-HT<sub>2C</sub>]] [[Receptor (biochemistry)|receptors]] with a [[Dissociation constant|K<sub>i</sub>]] of 0.26 nM at the human 5-HT<sub>2A</sub> 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.<ref>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</ref> This high potency and selectivity has made TCB-2 useful for distinguishing 5-HT<sub>2A</sub> mediated responses from those produced by other similar receptors.<ref>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</ref> 

== See also ==
* [[2C-B]]
* [[2CB-Ind]]
* [[Jimscaline]]

== References ==
{{Reflist}}


{{Hallucinogens}}
{{Serotonergics}}
{{Phenethylamines}}

[[Category:Psychedelic phenethylamines]]
[[Category:Organobromides]]
[[Category:Phenol ethers]]
[[Category:Benzocyclobutenes]]
[[Category:2Fix]]