6-Br-APB

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6-Br-APB
IUPAC ime
3-alil-6-bromo-1-fenil-1,2,4,5-tetrahidro-3-benzazepin-7,8-diol
Identifikatori
CAS broj135974-57-1 НеН
ATC kodnone
PubChemCID 11957483
ChemSpider8627436 ДаY
ChEMBLCHEMBL34095 ДаY
Hemijski podaci
FormulaC19H20BrNO2
Molarna masa374,27 g/mol
  • 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 ДаY
  • Key:KKZGFVAZUKHFAC-MRXNPFEDSA-N ДаY

6-Br-APB je sintetičko jedinjenje koje deluje kao selektivni agonist D1 receptora.[1] (R)-enantiomer je potentan pun agonist, dok (S) enantiomer ima D1 selektivnost, ali je slab parcijalni agonist.[2] (R)-6-Br-APB i slični D1-selektivni puni agonisti, kao što su SKF-81297 i SKF-82958 proizvode karakteristične anoreksične efekte, stereotipno ponašanje i samoadministraciju kod životinja. On ima sličan mada ne identičan profile sa dopaminergičkim stimulansima poput amfetamina.[3][4][5]

Reference[uredi | uredi izvor]

  1. ^ Neumeyer JL, Baindur N, Niznik HB, Guan HC, Seeman P (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. doi:10.1021/jm00116a004. 
  2. ^ Neumeyer JL, Kula NS, Baldessarini RJ, Baindur N (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. doi:10.1021/jm00086a016. 
  3. ^ Rosenzweig-Lipson S, Hesterberg P, Bergman J (1994). „Observational studies of dopamine D1 and D2 agonists in squirrel monkeys”. Psychopharmacology. 116 (1): 9—18. PMID 7862937. doi:10.1007/BF02244865. 
  4. ^ Weed MR, Woolverton WL (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. PMID 15464142. doi:10.1016/j.neuropharm.2004.07.007. 


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