99295-33-7
Chemical Structure
SKF-83566
- CAS No.: 99295-33-7
- Formula:C17H18BrNO
- Molecular Weight:332.23
IUPAC Name: 8-bromo-3-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol
InChIKey: XFTVOHWWEQGXLS-UHFFFAOYSA-N
SMILES: OC1=C(Br)C=C2CCN(C)CC(C3=CC=CC=C3)C2=C1
Biological Activity: SKF-83566 is an orally active, blood-brain barrier-permeable D1/D5 dopamine receptor antagonist with a Ki value of approximately 0.4-0.56 nM. SKF-83566 modulates locomotor behavior and spatial memory by blocking D1 receptors and inhibits glioblastoma progression by targeting the DRD1/c-Myc/UHRF1 pathway. SKF-83566 acts as an inhibitor of the dopamine transporter (DAT) and adenylyl cyclase 2 (AC2). SKF-83566 competitively binds to DAT to inhibit dopamine reuptake and non-competitively inhibits AC2 activity, thereby reducing cAMP accumulation. SKF-83566 is used in research areas such as dopaminergic system mechanisms, learning and memory, targeted intervention for glioblastoma, AC2 pathophysiology, antiparasitic drug screening, and synaptic plasticity (the "gating effect")[1][2][3][4][5][6][7][8].
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SKF-83566 | 99.66% | SKF-83566 is an orally active, blood-brain barrier-permeable D1/D5 dopamine receptor antagonist with a Ki value of approximately 0.4-0.56 nM. SKF-83566 modulates locomotor behavior and spatial memory by blocking D1 receptors and inhibits glioblastoma progression by targeting the DRD1/c-Myc/UHRF1 pathway. SKF-83566 acts as an inhibitor of the dopamine transporter (DAT) and adenylyl cyclase 2 (AC2). SKF-83566 competitively binds to DAT to inhibit dopamine reuptake and non-competitively inhibits AC2 activity, thereby reducing cAMP accumulation. SKF-83566 is used in research areas such as dopaminergic system mechanisms, learning and memory, targeted intervention for glioblastoma, AC2 pathophysiology, antiparasitic drug screening, and synaptic plasticity (the "gating effect"). | ||||||||||||||||||||
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SKF-83566 (Standard) | ≥98% | SKF-83566 (Standard) is the analytical standard of SKF-83566 (HY-103430A). This product is intended for research and analytical applications. SKF-83566 is an orally active, blood-brain barrier-permeable D1/D5 dopamine receptor antagonist with a Ki value of approximately 0.4-0.56 nM. SKF-83566 modulates locomotor behavior and spatial memory by blocking D1 receptors and inhibits glioblastoma progression by targeting the DRD1/c-Myc/UHRF1 pathway. SKF-83566 acts as an inhibitor of the dopamine transporter (DAT) and adenylyl cyclase 2 (AC2). SKF-83566 competitively binds to DAT to inhibit dopamine reuptake and non-competitively inhibits AC2 activity, thereby reducing cAMP accumulation. SKF-83566 is used in research areas such as dopaminergic system mechanisms, learning and memory, targeted intervention for glioblastoma, AC2 pathophysiology, antiparasitic drug screening, and synaptic plasticity (the "gating effect"). | ||||||||||||||||||||
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- [1]. Molloy AG, et al. The enantiomers of SK&F 83566, a new selective D-1 dopamine antagonist, stereospecifically block stereotyped behaviour induced by apomorphine and by the selective D-2 agonist RU 24213. Eur J Pharmacol. 1985 Oct 8;116(1-2):183-6.
- [2]. Stouffer MA, et al. SKF-83566, a D1-dopamine receptor antagonist, inhibits the dopamine transporter. Journal of neurochemistry. 2011 Sep;118(5):714-20. [Content Brief]
- [3]. Dai F, et al. Dopaminergic antagonists inhibit bile chemotaxis of adult Clonorchis sinensis and its egg production. PLoS neglected tropical diseases. 2020 Mar;14(3):e0008220.
- [4]. Huang H, et al. The effects of aging and dopaminergic inhibition on large scale maze learning in rhesus monkeys. Brain research bulletin. 2021 Oct;175:63-68.
- [5]. Jacoby SM, et al. SKF 83566 attenuates the effects of ghrelin on performance in the object location memory task. Neuroscience letters. 2011 Oct 31;504(3):316-20.
- [6]. Xue Z, et al. The dopamine receptor D1 inhibitor, SKF83566, suppresses GBM stemness and invasion through the DRD1-c-Myc-UHRF1 interactions. Journal of experimental & clinical cancer research : CR. 2024 Jan 22;43(1):25.
- [7]. Conley JM, et al. Development of a high-throughput screening paradigm for the discovery of small-molecule modulators of adenylyl cyclase: identification of an adenylyl cyclase 2 inhibitor. The Journal of pharmacology and experimental therapeutics. 2013 Nov;347(2):276-87. [Content Brief]
- [8]. Huang YY, et al. D1/D5 receptors and histone deacetylation mediate the Gateway Effect of LTP in hippocampal dentate gyrus. Learn Mem. 2014 Feb 18;21(3):153-60. [Content Brief]
Keywords
