6-Br-APB

6-Br-APB

6-Br-APB
Systematic (IUPAC) name
3-allyl-6-bromo-1-phenyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol
Clinical data
Legal status
?
Identifiers
CAS number  N
ATC code ?
PubChem
ChemSpider  YesY
ChEMBL  YesY
Chemical data
Formula C19H20BrNO2 
Mol. mass 374.27 g/mol
 N   

6-Br-APB is a synthetic compound that acts as a selective D1 agonist,[1] with the (R)-enantiomer being a potent full agonist, while the (S) enantiomer retains its D1 selectivity but is a weak partial agonist.[2] (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.[3][4][5]

References

  1. ^ Neumeyer JL, et al. (December 1991). "(+/-)-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 of Medicinal Chemistry 34 (12): 3366–71.  
  2. ^ Neumeyer JL, Kula NS, Baldessarini RJ, Baindur N (April 1992). "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 of Medicinal Chemistry 35 (8): 1466–71.  
  3. ^ Rosenzweig-Lipson S, Hesterberg P, Bergman J (September 1994). "Observational studies of dopamine D1 and D2 agonists in squirrel monkeys". Psychopharmacology 116 (1): 9–18.  
  4. ^ Weed MR, Woolverton WL (December 1995). "The reinforcing effects of dopamine D1 receptor agonists in rhesus monkeys". The Journal of Pharmacology and Experimental Therapeutics 275 (3): 1367–74.  
  5. ^ Barrett AC, Miller JR, Dohrmann JM, Caine SB (2004). "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". Neuropharmacology. 47 Suppl 1: 256–73.