6-Br-APB
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6-Br-APB
This article is about the dopamine D1 receptor agonist. For the amphetamine derivative, see 6-APB.
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| Systematic (IUPAC) name | |
| 3-allyl-6-bromo-1-phenyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 135974-57-1  |
| ATC code | ? |
| PubChem | CID 11957483 |
| ChemSpider | 8627436  |
| ChEMBL | CHEMBL34095 |
| Chemical data | |
| Formula | C19H20BrNO2 |
| Mol. mass | 374.27 g/mol |
| SMILES | eMolecules & PubChem |
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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, 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. 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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