2CB-Ind

{{Short description|Chemical compound}}

{{Use dmy dates|date=January 2024}}

{{Infobox drug

| Verifiedfields = changed

| verifiedrevid = 477216871

| IUPAC_name = (5-bromo-4,7-dimethoxy-2,3-dihydro-1H-inden-1-yl)methanamine

| image = 2CB-Indane.png

| tradename =

| legal_status = Uncontrolled

| routes_of_administration = Oral

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

| CAS_number = 912342-23-5

| ATC_prefix = none

| PubChem = 16086368

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

| ChemSpiderID = 17245022

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = ZMP92SN5X2

| ChEMBL = 424890

| C=12 | H=16 | Br=1 | N=1 | O=2

| smiles = COc1c(Br)cc(OC)c2c1CCC2CN

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

| StdInChI = 1S/C12H16BrNO2/c1-15-10-5-9(13)12(16-2)8-4-3-7(6-14)11(8)10/h5,7H,3-4,6,14H2,1-2H3

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

| StdInChIKey = HCLPGYNQMVSQIM-UHFFFAOYSA-N

}}

2CB-Ind is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, discovered in 1974 by Alexander Shulgin. It acts as a moderately potent and selective agonist for the 5-HT_2A and 5-HT_2C receptors, but unlike the corresponding benzocyclobutene derivative TCB-2 which is considerably more potent than the parent compound 2C-B, 2CB-Ind is several times weaker, with racemic 2CB-Ind having a K_i of 47nM at the human 5-HT_2A receptor, only slightly more potent than the mescaline analogue (R)-jimscaline.{{cite journal | vauthors = McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE | title = 1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists | journal = Journal of Medicinal Chemistry | volume = 49 | issue = 19 | pages = 5794–803 | date = September 2006 | pmid = 16970404 | doi = 10.1021/jm060656o | citeseerx = 10.1.1.688.9849 }}{{Cite thesis |type=PhD. |title=Towards a biophysical understanding of hallucinogen action |last=Braden |first=Michael Robert | name-list-style = vanc |year=2007 |publisher=Purdue University |id={{ProQuest|304838368}} }}