6-Br-APB

6-Br-APB
IUPAC ime
	3-alil-6-bromo-1-fenil-1,2,4,5-tetrahidro-3-benzazepin-7,8-diol
Identifikatori
CAS broj	135974-57-1
ATC kod	none
PubChem	CID 11957483
ChemSpider	8627436
ChEMBL	CHEMBL34095
Hemijski podaci
Formula	C19H20BrNO2
Molarna masa	374,27 g/mol
	SMILES c3ccccc3C2CN(CC=C)CCc(c1Br)c2cc(O)c1O; ;
	InChI 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 ; Key:KKZGFVAZUKHFAC-MRXNPFEDSA-N ;

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

^ 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.
^ 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.
^ 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.
^ 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.
^ 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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