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6-Br-APB: Wikis

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6-Br-APB
6BrAPB structure.png
IUPAC name
Identifiers
CAS number
PubChem 11957483
SMILES
Properties
Molecular formula C19H20BrNO2
Molar mass 374.271 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

6-Br-APB is a synthetic compound that acts as a selective dopamine receptor 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-81297 and SKF-82958 produce characteristic anorectic effects, stereotyped behaviour and self-administration in animals, with a similar but not identical profile to that of dopaminergic stimulant drugs such as amphetamine.[3][4][5]

References

  1. ^ Neumeyer JL, Baindur N, Niznik HB, Guan HC, Seeman P (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. PMID 1684995.  
  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. PMID 1533424.  
  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. PMID 7862937.  
  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. PMID 8531104.  
  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. doi:10.1016/j.neuropharm.2004.07.007. PMID 15464142.  
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