TCB-2

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TCB-2
TCB-2.png
Systematic (IUPAC) name
1-[(7R)-3-bromo-2,5-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methanamine
Clinical data
Legal status
  • Uncontrolled
Routes of
administration
Oral
Identifiers
CAS Number 912440-88-1 YesY
912342-36-0 (hydrobromide)
ATC code none
PubChem CID: 16086382
Chemical data
Formula C11H14BrNO2
Molecular 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 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]

See also

References

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  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
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