6-Br-APB

{{Short description|Chemical compound}}

{{about|the dopamine D1 receptor agonist|the amphetamine derivative|6-APB}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 477225692

| IUPAC_name = 3-allyl-6-bromo-1-phenyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol

| image = 6-Br-APB Structure.svg

| image2 = 6-Br-APB-3D-balls.png

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

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

| CAS_number = 135974-57-1

| ATC_prefix =

| ATC_suffix =

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

| StdInChI = 1S/C19H20BrNO2/c1-2-9-21-10-8-14-15(11-17(22)19(23)18(14)20)16(12-21)13-6-4-3-5-7-13/h2-7,11,16,22-23H,1,8-10,12H2/t16-/m1/s1

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

| StdInChIKey = KKZGFVAZUKHFAC-MRXNPFEDSA-N

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

| ChEMBL = 34095

| PubChem = 11957483

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

| ChemSpiderID = 8627436

| C=19 | H=20 | Br=1 | N=1 | O=2

| smiles = c3ccccc3C2CN(CC=C)CCc(c1Br)c2cc(O)c1O

}}

6-Br-APB is a synthetic compound that acts as a selective D₁ agonist,{{cite journal |vauthors =Neumeyer JL |title=(+/-)-3-Allyl-6-bromo-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3- benzazepin, a new high-affinity D1 dopamine receptor ligand: synthesis and structure-activity relationship |journal=Journal of Medicinal Chemistry |volume=34 |issue=12 |pages=3366–71 |date=December 1991 |pmid=1684995 |doi= 10.1021/jm00116a004|display-authors=etal}} with the (R)-enantiomer being a potent full agonist, while the (S) enantiomer retains its D₁ selectivity but is a weak partial agonist.{{cite journal |vauthors =Neumeyer JL, Kula NS, Baldessarini RJ, Baindur N |title=Stereoisomeric probes for the D1 dopamine receptor: synthesis and characterization of R-(+) and S-(-) enantiomers of 3-allyl-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine and its 6-bromo analogue |journal=Journal of Medicinal Chemistry |volume=35 |issue=8 |pages=1466–71 |date=April 1992 |pmid=1533424 |doi= 10.1021/jm00086a016}} (R)-6-Br-APB and similar D₁-selective full agonists like SKF-81,297 and SKF-82,958 produce characteristic anorectic effects, stereotyped behaviour and self-administration in animals, with a similar but not identical profile to that of dopaminergic stimulants such as amphetamine.{{cite journal |vauthors =Rosenzweig-Lipson S, Hesterberg P, Bergman J |title=Observational studies of dopamine D1 and D2 agonists in squirrel monkeys |journal=Psychopharmacology |volume=116 |issue=1 |pages=9–18 |date=September 1994 |pmid=7862937 |doi= 10.1007/BF02244865|s2cid=24204026 }}{{cite journal |vauthors =Weed MR, Woolverton WL |title=The reinforcing effects of dopamine D1 receptor agonists in rhesus monkeys |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=275 |issue=3 |pages=1367–74 |date=December 1995 |pmid=8531104 }}{{cite journal |vauthors =Barrett AC, Miller JR, Dohrmann JM, Caine SB |title=Effects of dopamine indirect agonists and selective D1-like and D2-like agonists and antagonists on cocaine self-administration and food maintained responding in rats |journal=Neuropharmacology |volume=47 |pages=256–73 |year=2004 |issue=Suppl 1 |pmid=15464142 |doi=10.1016/j.neuropharm.2004.07.007 |s2cid=2959198 }}