2CBCB-NBOMe

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 452168959

| IUPAC_name = N-[(3-bromo-2,5-dimethoxy-bicyclo[4,2,0]octa-1,3,5-trien-7-yl)methyl]-1-(2-methoxyphenyl)methanamine

| image = 2CBCB-NBOMe-skeletal.svg

| tradename =

| legal_DE = NpSG

| legal_UK = Class A

| legal_status =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 1354634-09-5

| PubChem = 57483909

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 26234935

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = WGI3S41A26

| C=19 | H=22 | Br=1 | N=1 | O=3

| smiles = COc1ccccc1CNCC3c2c(C3)c(OC)c(Br)cc2OC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C19H22BrNO3/c1-22-16-7-5-4-6-12(16)10-21-11-13-8-14-18(13)17(23-2)9-15(20)19(14)24-3/h4-7,9,13,21H,8,10-11H2,1-3H3/t13-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CLSBQRBXTFTLEX-ZDUSSCGKSA-N

}}

2CBCB-NBOMe (NBOMe-TCB-2) is a compound indirectly derived from the phenethylamine series of hallucinogens, which was discovered in 2007 at Purdue University as part of the ongoing research program of the team led by David Nichols focusing on the mapping of the specific amino acid residues responsible for ligand binding to the 5HT_2A receptor. 2CBCB-NBOMe acts as a potent and selective agonist for the 5-HT_2A and 5-HT_2C receptors, with a Ki of 0.27 nM at the human 5-HT_2A receptor, a similar potency to other agonists such as TCB-2, NBOMe-2C-I and Bromo-DragonFLY.{{Cite thesis |type=Ph.D. |title=Towards a biophysical understanding of hallucinogen action | vauthors = Braden MR |year=2007 |publisher=Purdue University |id={{ProQuest|304838368}} }}