Chemistry:6-Br-APB

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Short description: Chemical compound
6-Br-APB
6-Br-APB Structure.svg
6-Br-APB-3D-balls.png
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC19H20BrNO2
Molar mass374.278 g·mol−1
3D model (JSmol)
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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. "(+/-)-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. December 1991. doi:10.1021/jm00116a004. PMID 1684995. 
  2. "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. April 1992. doi:10.1021/jm00086a016. PMID 1533424. 
  3. "Observational studies of dopamine D1 and D2 agonists in squirrel monkeys". Psychopharmacology 116 (1): 9–18. September 1994. doi:10.1007/BF02244865. PMID 7862937. 
  4. "The reinforcing effects of dopamine D1 receptor agonists in rhesus monkeys". The Journal of Pharmacology and Experimental Therapeutics 275 (3): 1367–74. December 1995. PMID 8531104. 
  5. "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. 2004. doi:10.1016/j.neuropharm.2004.07.007. PMID 15464142.