TCB-2

TCB-2 is a hallucinogen discovered in 2006 by Thomas McLean working in the lab of David Nichols at Purdue University.^[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 0.26 nM at the human 5-HT_2A receptor.

TCB-2

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In General Unscheduled
Identifiers
IUPAC name [(7R)-3-Bromo-2,5-dimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl]methanamine
CAS Number	912440-88-1 Y 912342-36-0 (hydrobromide)
PubChem CID	16086382
ChemSpider	17245036
UNII	8U6Z2MP6H7
ChEMBL	ChEMBL379637
CompTox Dashboard (EPA)	DTXSID201027451
Chemical and physical data
Formula	C11H14BrNO2
Molar mass	272.142 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1c(Br)cc(OC)c2c1CC2CN
InChI InChI=1S/C11H14BrNO2/c1-14-9-4-8(12)11(15-2)7-3-6(5-13)10(7)9/h4,6H,3,5,13H2,1-2H3/t6-/m0/s1 Key:MPBCKKVERDTCEL-LURJTMIESA-N
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In drug-substitution experiments in rats, TCB-2 was found to be of similar potency to both LSD and Bromo-DragonFLY, ranking it among the most potent phenethylamine hallucinogens yet discovered.^[1] This high potency and selectivity has made TCB-2 useful for distinguishing 5-HT_2A receptor-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-HT_2A 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] It has also been found to produce rapid antidepressant-, anti-anhedonic-, and anxiolytic-like effects in animals.^[7]

See also

• β-Methyl-2C-B
• 2CB-Ind
• 2CBCB-NBOMe
• Ivabradine
• Jimscaline
• LPH-5 (drug)
• S33005
• ZC-B