This article is about the dopamine D1 receptor agonist. For the amphetamine derivative, see 6-APB .
6-Br-APB
3-allyl-6-bromo-1-phenyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol
CAS Number 135974-57-1 N PubChem CID ChemSpider ChEMBL CompTox Dashboard (EPA ) Formula C 19 H 20 Br N O 2 Molar mass 374.278 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
Y Key:KKZGFVAZUKHFAC-MRXNPFEDSA-N
Y
N Y (what is this?)
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 [ ]
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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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# WHO-EM
‡ Withdrawn from market
Clinical trials :
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D1 -like
Agonists
Benzazepines : 6-Br-APB
Fenoldopam
SKF-38,393
SKF-77,434
SKF-81,297
SKF-82,958
SKF-83,959
Trepipam
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CY-208,243
Dihydroergocryptine
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Etilevodopa
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PF-6649751
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SKF-89,145
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See also: Receptor/signaling modulators
Adrenergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins