6-Br-APB

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]

This article is about the dopamine D1 receptor agonist. For the amphetamine derivative, see 6-APB.
6-Br-APB
Identifiers
  • 3-allyl-6-bromo-1-phenyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H20BrNO2
Molar mass374.278 g·mol−1
3D model (JSmol)
  • c3ccccc3C2CN(CC=C)CCc(c1Br)c2cc(O)c1O
  • InChI=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 checkY
  • Key:KKZGFVAZUKHFAC-MRXNPFEDSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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. doi:10.1021/jm00116a004. 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. doi:10.1021/jm00086a016. 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. doi:10.1007/BF02244865. PMID 7862937. S2CID 24204026.
  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. S2CID 2959198.


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