TCB-2

TCB-2
	Racemic TCB-2 structure
	TCB-2 ball-and-stick model
Clinical data
Other names	2CBCB; 2C-BCB; 6,β-Methylene-2C-B; 2C-TCB
Routes of; administration	Unknown
Drug class	Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Legal status
Legal status	In general unscheduled;
Pharmacokinetic data
Duration of action	Unknown
Identifiers
	IUPAC name (3-bromo-2,5-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methanamine;
PubChem CID	16046239;
ChemSpider	13174651;
ChEBI	CHEBI:91625;
CompTox Dashboard (EPA)	DTXSID201027451 ;
Chemical and physical data
Formula	C11H14BrNO2
Molar mass	272.142 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC(=C(C2=C1C(C2)CN)OC)Br;
	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; Key:MPBCKKVERDTCEL-UHFFFAOYSA-N;
	(verify)

TCB-2, also known as 2CBCB or 2C-BCB, is a putative psychedelic drug of the phenethylamine, 2C, and benzocyclobutene families related to 2C-B. It is a cyclized phenethylamine and is the derivative of 2C-B in which the β position has been connected to the 6 position by a methylene bridge to form a benzocyclobutene ring system. It is unclear whether TCB-2 produces hallucinogenic effects in humans and its route of administration and properties such as dose and duration are unknown.

The drug is a highly potent serotonin receptor agonist, including of the serotonin 5-HT_2A receptor among others. TCB-2 produces psychedelic-like effects in animals. It may be among the most potent known serotonin 5-HT_2A receptor agonists and psychedelic phenethylamines. TCB-2 is often employed as its more potent and selective enantiomer (R)-TCB-2 in scientific research.

TCB-2 was first described in the scientific literature by Thomas McLean and colleagues of the lab of David E. Nichols at Purdue University in 2006. It was encountered as a novel designer drug by 2018, though it appears to be very rare. The drug is not an explicitly controlled substance in the United States and is fully legal for use in scientific research in this country. TCB-2 was suggested as an alternative and replacement of the widely employed DOI for use in research in 2025.